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Vacation Rentals in Summerland Key, FL and nearby

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    All 52 Rentals in the Summerland Key Area
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    From
    $300
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    1 / 15
    1 of 5 stars (1) Terrible
    Summerland Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    $1,250
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    1 / 18
    Summerland Key
    3 Bedrooms / 10 Bathrooms / Sleeps 8
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    $285
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    1 / 30
    Summerland Key
    2 Bedrooms / 3 Bathrooms / Sleeps 10
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    $20,000
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    1 / 9
    Summerland Key
    7 Bedrooms / 5 Bathrooms / Sleeps 14
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    Amenities & Details
    • Deck
    • Waterfront
    • Washer
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located 25 miles from Key West, this unique estate property has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon fishing, lobstering and privacy. This newly constructed estate just completed in July 2009 is located on 1 acre adjacent to wild life reserve... View all property information
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    Summerland Key, Lower Keys 33042
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    $5,988
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    1 / 8
    4.5 of 5 stars (2) Very good
    Summerland Key
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Internet Access
    • TV
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Lovely three Bedroom/2 Bath home with pool and hot tub located on Summerland Key. Mile marker 25. Deep water swimming canal with boat ramp and dockage. Large screened in porch for outdoor dining and BBQ grill. Tropical landscape and extra sleeping. Sleeps up to 8. 28 day rental. Please... View all property information
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    Summerland Key, Lower Keys 33042
    5 of 5 stars Reviewed June 9, 2015
    Island Living is quite comfortable for us. Plenty of room for friends. Quiet, safe neighborhood. Easy ride to shopping and Key West. The pool is very nice. Boating access is...
    4 of 5 stars Reviewed April 2, 2012
    The home and pool were clean, comfortable and nicely furnished. Kitchen is simply furnished and could use a variety of serving dishes and sharp knives. You will need to purchase...
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    $170
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    1 / 12
    4 of 5 stars (1) Very good
    Summerland Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Deck
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Seasonal Rates Start at 1190.00 per week based on 7 night miniimum stay. Extremely private two bedroom two full bathrooms on beautiful Little Torch Key , Oceanside . Deep Water swimming canal . Plenty of room for docking and parking of trailers etc... house was completely renovated less than... View all property information
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    Summerland Key, Lower Keys 33042
    4 of 5 stars Reviewed April 27, 2015
    There was plenty of parking for our truck and boat trailer. We liked the fact that the boat dock was inset for more protection of the boat, but parking into it was a little...
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    $329
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    1 / 8
    5 of 5 stars (1) Excellent
    Summerland Key
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Waterfront
    • Hot Tub
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open.. This is a spacious oceanfront 4/2 home with a heated pool/spa and breathtaking open water views! It is located on beautiful Ramrod Key 110 ft concrete... View all property information
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    Location Information
    Summerland Key, Lower Keys 33042
    5 of 5 stars Reviewed November 10, 2014
    This oceanfront home in Ramrod Key is beautiful! It is clean and well kept. The owner ensures that you are comfortable in your home away from home. The view is gorgeous. The...
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    $125
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    1 / 15
    3 of 5 stars (3) Average
    Summerland Key
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Waterfront
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    'The Pisces House' is a cozy cottage perfectly located on a deep water canal with open water views. This adorable 'keys style' cottage has everything you need for a relaxing getaway. This 1 bedroom/2bath cottage features a FULL kitchen, quaint living quarters with a sofa bed, and a peaceful patio... View all property information
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    Location Information
    Summerland Key, Lower Keys
    1 of 5 stars Reviewed June 18, 2015
    We booked this rental after seeing the the review off tripadvisor so thought it would be o k , but when we arrived our hearts sank . The house is in serious state of disrepair the...
    5 of 5 stars Reviewed June 1, 2015
    We stayed for 9 nights. Marianne was easy to communicate with prior to our arrival. In addition, she provided a cell phone contact in case there were any issues. We arrived at 4PM...
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    $393
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    1 / 3
    Summerland Key
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Boat Available
    • Water Views
    • Satellite TV
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished... View all property information
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    Location Information
    Summerland Key, Lower Keys 33042
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    $250
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    1 / 18
    Summerland Key
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Stereo System
    • Waterfront
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Big Torch Key is reminiscent of the Florida Keys 40 years ago,seclusion and peace invade your senses immediately, sunset views that will take your breath away. Torchview has an open floor plan (kitchen/living room/dining room) with a huge master suite(king bed)and two other bedrooms (one with a... View all property information
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    Location Information
    Summerland Key, Lower Keys 33042
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    $321
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    1 / 22
    Summerland Key
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Waterfront
    • Dryer
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome Tropical Villa which is a large home on a clear, flow through swimming canal. With 65 feet of seawall, and 4.5 feet of control depth, even large sailboats can be accommodated here! We only three minutes to the ocean, only fifteen minutes to Looe Key reef (one of the Key's premier dive... View all property information
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    Location Information
    Summerland Key, Lower Keys 33042

    The following rentals are within 5 miles of Summerland Key, Lower Keys, Florida Keys, Florida.

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    $130
    / Night
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    1 / 24
    5 of 5 stars (7) Excellent
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Water Views
    • Shared Tennis Court
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a very cute 24x32 two bedroom, two bathroom home located on mile marker 23 just 19 miles from the entrance to key west. The house has a very nice fully equipped kitchen. All the floors are tile with the exception of the master bedroom which is bamboo. The master bedroom comes with its... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed June 4, 2015
    First of all the owners were very helpful and informative from booking all the way through our stay. I went with my husband and two daughters and stayed seven nights. We found the...
    5 of 5 stars Reviewed March 24, 2015
    Stayed for a month and a half, wish we could stay longer. Randy and Donna were very accommodating and responded to any requests. The unit was clean and well equipped, has a...
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    From
    $110
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    1 / 25
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Shared Tennis Court
    • Waterfront
    • Satellite TV
    • Water Views
    • Watersports Nearby
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    From
    $720
    / Week
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    1 / 17
    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Internet Access
    • Water Views
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Children's Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Tropical, Affordable Rental in Gated Community, Wi-Fi & Gas Grill Colorful tropical vacation home. The living room nicely decorated with tropical flare, has a flat screen TV with DVD, Directv W/DVR,two sofas, one is a queen size sleeper and comfortable bamboo chair. Dining area conveniently... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    From
    $235
    / Night
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    1 / 24
    5 of 5 stars (1) Excellent
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Hot Tub
    • Ping Pong Table
    • Swingset
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Dock you boat or jet skis behind this nicely decorated 2 bedroom 2 bathroom(sleeps up to six people) on a deep water canal just a stone's throw from the open water of the Atlantic Ocean. On-site amenities include an 80 foot heated swimming pool, seperate pool for the kiddies, jacuzzi, marina, boat... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed October 25, 2014
    Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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    $500
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    1 / 14
    3.5 of 5 stars (7) Average
    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Stereo System
    • Watersports Nearby
    • Air Conditioning
    • DVD Player
    • Children's Pool
    • Satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    In response to the 1 review that gave us 1 star, I would like to report all issues have been addressed. We have new kitchen, dinning room and bathroom flooring, from the bottom up. it is all new and reinforced.( no soft spots) We have replaced the toilet and vanity in the bathroom. We have a new... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed July 24, 2015
    Check-in with resort guard house (this is a gated community) was quick and easy; only accepts cash and checks however for resort fees, so be prepared for that. The rental is just...
    4 of 5 stars Reviewed May 21, 2015
    The place is somewhat shabby with obvious water damage but sparkling clean. The floor has several soft spots. There are plenty of dishes and a nice gas grill. Besides, you're in...
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    $1,500
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    1 / 19
    4 of 5 stars (1) Very good
    Cudjoe Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • DVD Player
    • Washer
    • Stereo System
    • Satellite TV
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed May 6, 2015
    This rental was perfect for our week trip to the Keys. It was clean and well stocked with cooking utensils to allow us to BBQ up some fresh fish a few nights. The beds were...
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    $107
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    1 / 11
    Ramrod Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • DVD Player
    • Water Views
    • Air Conditioning
    • Internet Access
    • Private Fishing...
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    10 minutes to the OCEAN - DEEP WATER CANAL READY FOR LOBSTER SEASON!!!!! 3 bedroom 2 bath Stilt house on a canal. Nice screened in porch (mosquito proofed) to relax in the evening. 10 minutes to the Ocean!! Just 25 minutes to Key West. Walking distance to Looe Key Reef Resort and Tikki Bar... View all property information
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    Location Information
    Ramrod Key, Florida Keys 330402
    From
    $236
    / Night
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    1 / 23
    5 of 5 stars (1) Excellent
    Little Torch Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    3 bedroom, 2 full bathroom, 1 outdoor shower, Sleeps 8 This three bedroom home boasts of many special features and offers a perfect location. The unit can sleep 6-8 . Laying at the corner of Dolphin Marina and Little Palm Island you'll vacation in one of Key's finest neighborhoods. A 60 second... View all property information
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    Little Torch Key, Florida Keys 33043
    5 of 5 stars Reviewed August 7, 2014
    This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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    $400
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    1 / 32
    4.5 of 5 stars (35) Very good
    Cudjoe Key, FL
    5 Bedrooms / 3 Bathrooms / Sleeps 14
    Overview Reviews (35) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Hot Tub
    • Private Outdoor...
    • Playground
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Great for large groups, White Ibis Inn has a Main and Guest House, with a total of 5 bedrooms, 3 baths, and 2 kitchens. There's plenty of room for play, peace, and parking. The property is situated on Cudjoe Key, MM21, about a 20 minute drive to Key West. It's a safe area with older residents and... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed April 21, 2015
    We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we...
    5 of 5 stars Reviewed February 7, 2015
    This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group...
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    $1,100
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    1 / 54
    Cudjoe Key, FL
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Water Views
    • Satellite TV
    • Deck
    • Stereo System
    • Air Conditioning
    • Private Fishing...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size Sleep Number Bed - Fully... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
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    $242
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    1 / 29
    4 of 5 stars (10) Very good
    Ramrod Key, FL
    4 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Reviews (10) Make Inquiry
    Amenities & Details
    • TV
    • Pool Table
    • DVD Player
    • Waterfront
    • Private Fishing...
    • Air Conditioning
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    House and AMERICAN CARRIBEAN VILLA near to Key West, Florida in Ramrod Key, visit: www.villamarquesa.com for our Official Prices, Calandar and Photos and for our Sister Property Casa Serenity http://www.flipkey.com/ramrod-key-vacation-rentals/p300040/ See us in on TV as the most affordable rental... View all property information
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    Location Information
    Ramrod Key, Florida Keys 33042
    1 of 5 stars Reviewed July 13, 2015
    Beware!! the owner,we rented house from June 27 until July 5 2015.after giving him 2450.00 plus 1000.00 deposit he notified me we could not get in house until June 28th or...
    5 of 5 stars Reviewed April 27, 2015
    My wife and I had a spectacular week staying at Villa Marquesa. The owner answered all our questions and was prompt in returning phone calls. He provided tips to local...
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    $3,500
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    1 / 11
    Cudjoe Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Linens Provided
    • Wi-Fi
    • Parking
    • Grill
    • Ocean Views
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    CANAL FRONT HOME WITH 3 BEDROOM AND 2 BATH AND POSSIBLE 4TH BEDROOM , TWO ENTRANCE HOME ONE TO LIVING ROOM AND OTHER TO COVERED DECK OVERLOOKING CANAL. GLASS SLIDERS TO BEAUTIFUL VIEWS OFF 2 BEDROOMS . ALL NEW FURNITURE AND STAINLESS STEEL APPLIANCES, GRANITE COUNTER TOPS AND COFFEE NOOK IN... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
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    $650
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    1 / 6
    5 of 5 stars (1) Excellent
    Little Torch Key, FL
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Internet Access
    • Water Views
    • Dryer
    • Air Conditioning
    • Boat Available
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Private Home, 6 Bedrooms + Convertible Bed(s), 4 Baths (Sleeps 10-16) Unique Property that has its own private boat basin and boat ramp. Dockage, shopping, scuba diving, off shore fishing, back county fishing, lobstering and privacy. This classic Florida Keys compound is located on Pine Channel,... View all property information
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    Location Information
    Little Torch Key, Florida Keys 33402
    5 of 5 stars Reviewed March 17, 2014
    We had a great time and a relaxing vacation. The house is great lots of room in main house and the guest house has 2 bedrooms, 1 bathroom kitchen and living room. You are supplied...
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    $2,810
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    1 / 20
    5 of 5 stars (7) Excellent
    Cudjoe Key, FL
    4 Bedrooms / 3 Bathrooms / Sleeps 14
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    • Waterfront
    • Water Views
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks.... View all property information
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    Location Information
    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed April 17, 2015
    Great location. As described. A multimillion dollar view from back porch. Well maintained grounds and a private master suite upstairs. There are dogs next door that might be an...
    5 of 5 stars Reviewed July 28, 2014
    We rented this home for a week in July for a quiet family getaway. This was my first time renting a home in the keys, I have done so many times in the Smokey Mountains but never...
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    5 of 5 stars (6) Excellent
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Water Views
    • Waterfront
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed January 14, 2015
    A lovely waterfront home facing south on Cudjoe Bay. Outside you have palms, a dock, hot tub, pool, hammock, bikes, kayaks, adirondack chairs, deck, umbrella table, flowers...
    5 of 5 stars Reviewed January 10, 2015
    In October I contacted owner of this property and I was glad it's was available! We were absolute in love with place from the moment we saw it! It has everything you've ever need...
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    4.5 of 5 stars (12) Very good
    Cudjoe Key, FL
    6 Bedrooms / 4 Bathrooms / Sleeps 18
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    Amenities & Details
    • Water Views
    • Satellite TV
    • Air Conditioning
    • Washer
    • Deck
    • Internet Access
    • Waterfront
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. Floating dock is great to fish and swim... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed June 18, 2015
    12 of our family came down from NC & VA to celebrate a college graduation and fulfill some bucket list items. It was a classic road trip and the very best vacation imaginable. We...
    3 of 5 stars Reviewed June 10, 2015
    Went to see the property before signing the lease. Everything is as I remembered. Nice big screen porch facing the open water. Room for everyone on that porch. Big roomy kitchen...
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    5 of 5 stars (1) Excellent
    Cudjoe Key, FL
    4 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Water Views
    • Waterfront
    • Internet Access
    • Private Outdoor...
    • TV
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful four thousand plus square foot home located on Cudjoe Key. Private beach and 30 foot swimming pool with 10 foot waterfall hot tub. Huge master suite overlooking the ocean. The house comes with BBQ grill and single and double kayaks. Spectacular views can be enjoyed from the screened... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed January 5, 2014
    We are 3 families, 5 adults and 3 teenagers. The 4 bedrooms are each very private and quiet. There are 2 master bedrooms each with ensuite bathrooms; 1 upstairs and 1 downstairs...
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    5 of 5 stars (1) Excellent
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    180 degree wrap around porch with patio furniture. 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. Panoramic view from front room with three sets of glass sliders. TV, DVD player, queen sleeper sofa. Kitchen island, side by side refrigerator with water... View all property information
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    Cudjoe Key, Florida Keys 33042
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    4 of 5 stars (1) Very good
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Panoramic open water view! Enjoy this hypnotic view from living room, dining area and kitchen. Unusually large 50' seawall with cleats, swim ladder and fish cleaning table. Flat screen TV with DVD conveniently placed for viewing from living room, dining area and kitchen. Living area has... View all property information
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    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed October 27, 2014
    Enjoyed our stay. Lots to see and do! The view was breathtaking and the resort was in a great location. The pools and hot tub were very convenient. We would definitely visit again!
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    5 of 5 stars (1) Excellent
    Cudjoe Key, FL
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 5 bedroom 3 bath house with pool on ocean front property on Highway, located just 20 miles away from the famous Key west complete with WiFi. This lovely home has it's own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill,... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed June 23, 2015
    2015 marked one of the "mile-stone" birthdays. I've been planning this trip for a year and it took me almost 6 months to find the Royal Key House in Cudjoe Key, 20 minutes from...
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    4.5 of 5 stars (3) Very good
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Satellite TV
    • Patio
    • Refrigerator
    • Washer
    • DVD Player
    • Dryer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    For a TROPICAL VACATION come to our beautiful designer furnished 2BD/2BA cottage at VENTURE OUT RESORT on Cudjoe Key. We pride our home on its comfort and cleanliness and have been told we have one of the nicest 2BD/2BA NON-WATERFRONT RENTAL HOMES in Venture Out Resorts. Olympic size pool, hot... View all property information
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    Cudjoe Key, Florida Keys 33042
    3 of 5 stars Reviewed July 18, 2015
    This place is fine if you do not mind small. This is a small mobile home close to water in a large community. The place was not real clean, mostly the floors were dirty and our...
    5 of 5 stars Reviewed April 8, 2015
    We loved our place and would recommend it to anyone! It was very comfortable and had everything we needed to make our stay very comfortable for the week! Venture Out has all the...
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    5 of 5 stars (1) Excellent
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Microwave
    • Satellite TV
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Relax enjoying water views from both front and back decks. This home was recently redecorated with comfy upscale furniture and art. Large open living room has flat screen TV with DVD. Furniture is microfabric sleeper sofa, love seat and an armchair with hassock. Kitchen is conveniently laid... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed November 10, 2014
    We had a wonderful stay at Venture Out. It was very peaceful and enjoyable. The internet was fast and the cable TV had plenty of channels. The appliances and furniture are modern...
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    4 of 5 stars (1) Very good
    Cudjoe Key, FL
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Grill
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    38' seawall with dock posts, cleats, fish cleaning table and swim ladder. This home has a large covered, screened porch with upscale patio furniture including a large table with four comfortable chairs, a swinging love seat and several swivel chairs. The master bedroom has a queen size bed with... View all property information
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    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed April 23, 2014
    The unit was nice and clean. Everything worked good. The screen porch was very popular.. I did not have a chance to have my boat there but the dock area was in good shape. The...
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    4 of 5 stars (1) Very good
    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Freshly redecorated canal front home. Living room has a 32' flat screen TV with DVD, two sleeper sofas . Master bedroom has full size bed, mirror closet and a vanity with drawers. Guest bedroom has twin trundel bed with mirror closet and slider doors to patio and canal. Spacious open kitchen... View all property information
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    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed November 23, 2013
    Two bedrooms, living room, full kitchen and bathroom was enough to accommodate five people. Place is quiet, but not very close to public beaches. For the end of October there are...
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    4.5 of 5 stars (2) Very good
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    You will fall in love with the happy colorful tropical decorations in this canal front home. 35' seawall with whips, high end dock posts, cleats, swim ladder. Large table, comfortable patio chairs and lounging furniture to enjoy the seawall view and shade under the home. Upper deck has a view of... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed March 31, 2015
    Very nice clean house. Could have used a couple more needed utensils in the kitchen. But, other than that very clean canal, great security, and lots of activities. Great for...
    4 of 5 stars Reviewed January 3, 2015
    Nice property on a friendly resort. Goods and bad points:- Small shop with a simple selection of key essentials Onsite parking underneath the property Plenty of storage No...
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    3 of 5 stars (2) Average
    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Canal front home with spacious ambiance. 35’ seawall with dock posts, cleats, fish cleaning table with hose and outdoor shower. Covered back deck with ceiling fan, drop shades and patio furniture. Living room has large Flat Screen TV with DVD, sleeper sofa, two rockers, recliner and door to... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed July 19, 2015
    We had a very great family vacation. We couldn't have asked for a better place. Everything we wanted and more. We will be back.
    1 of 5 stars Reviewed September 18, 2014
    Upon entering the house, floors were dirty. Cabinets had roach feces all through out and live roaches in the oven drawer and in cabinets. Did not cook food in the home the last...
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    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Boat Available
    • DVD Player
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Comfortable and charming, this newer stilt home has everything you could want for a vacation for just the two of you, a few friends, or the whole family! Fantastic waterfront open canal views. Located on a 60' wide canal, you can bring your powerboat, jet ski, kayak, or what have... View all property information
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    Cudjoe Key, Florida Keys 33042
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    Cudjoe Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Washer
    • DVD Player
    • Dryer
    • Air Conditioning
    • Stereo System
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a spacious, open floor plan, Three bedrooms, Two Bathrooms, 6 people accomodation, brightly painted colors, beautifully furnished. Relax in the upper covered porch or down below to the open and spacious patio leading to the pool. Outdoor Tiki shower hut. The grounds are landscaped with an... View all property information
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    Cudjoe Key, Florida Keys
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    Ramrod Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Deck
    • Internet Access
    • Boat Available
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    3bd/2ba home w/ sliding glass doors off entire back of house provides never ending views of the Atlantic Ocean Fully equipped home just 25 min from Key West, 10 minutes from beautiful Bahia Honda State Park. Deep water access w/ mean draft of 3ft. Ramrod Key features Looe key reef for excellent... View all property information
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    Ramrod Key, Florida Keys 33042
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    Ramrod Key, FL
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Boat Available
    • Hot Tub
    • Waterfront
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    KEY WEST only a 25 minutes drive. Bahia Honda (Beach) National Park 10 minutes...local - Looe Key National Marine Santuary for the Best Diving/Snorkling - 5 mile of reef Near Content Key Reef (Gulf side) - Best Lobstering! Depth 8-15' Good for Novice to experienced snorklers and divers. VERY... View all property information
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    Ramrod Key, Florida Keys 33042
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    Cudjoe Key, FL
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Private Outdoor...
    • Dryer
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Deck
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    3 Bedrooms, 3 Bathrooms, Sleeps 8 L’Anquesa – The Angel’s Key Luxury Amenities Include: Total renovation completed January 2014 2 master bedrooms suites with king beds, ensuite baths, flatscreen TVs and surround sound with incredible panoramic views 1 Guest room with 2 Queen Beds... View all property information
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    Cudjoe Key, Florida Keys
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    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Tropical whimsy merged with designer chic! Living room has a wall of windows overlooking tropically landscaped patio. Patio has glass top dining table, two (lie down and never get up) lounge chairs, colorful picnic table, three shade umbrellas and large gas grill. Living room has a flat screen... View all property information
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    Cudjoe Key, Florida Keys 33042
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    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Designer elegant canal front home on unusual seawall accommodating two boats! Corner dock 49' one side and 39' other side, dock posts, cleats, swim ladder and mosaic picnic table. Partially covered deck with patio furniture to enjoy scenery. Living room is open with double glass sliders across... View all property information
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    Cudjoe Key, Florida Keys
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    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Cute as can be! Tastefully decorated with cozy comfortable furniture. Close to all of the amenities, including the pool, community store, marina, recreation hall, bocce ball courts, etc. Queen bed in one room and a double bed in the second bedroom Nice, large deck on front of home with table... View all property information
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    Cudjoe Key, Florida Keys
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    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Microwave
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This charming two bedroom, two bath home has been totally renovated and updated for your comfort and enjoyment! Spacious, open floor plan in the living room/dining room/kitchen area is excellent for entertaining!! Nice covered patio area - perfect for relaxing or reading your favorite book. 35'... View all property information
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    Cudjoe Key, Florida Keys 33042
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    Cudjoe Key, FL
    1 Bedroom / 1 Bathroom / Sleeps 4
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This clean and very well maintained canal front vaction home features 1Bd/1Ba with master bedroom king size bed with access to the full size bathroom. Living room features a futon sleeper with 32' flat screen television with DVD player. 35'concrete seawall features dock posts, cleats, swim... View all property information
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    Cudjoe Key, Florida Keys 33042
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    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Affordable vacation home beautifully decorated in peaceful pastel colors. This home has many nice features including being bright, spacious and tropically decorated. The living room area has a Flat screenTV with DVD & VCR, queen size sleeper sofa, glass top table and comfy chairs. Master bedroom... View all property information
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    Cudjoe Key, Florida Keys 33042
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    Cudjoe Key, FL
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Two bedroom home with ocean view from living room and deck. Living room has a queen size sleeper sofa, flat screen TV.Smart TV with Wifi for your devices. Kitchen is open and inviting with wood tone cabinets. Dining area located in a pleasant alcove near kitchen has a glass top table with seating... View all property information
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    Cudjoe Key, Florida Keys 33042
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    $171
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    Cudjoe Key, FL
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Wrap around open water view with a huge 61' concrete dock/seawall, complete with cleats, padded aluminum dock posts,mooring whip holders,and hose. Covered deck with lounge furniture to dine out or enjoy an evening drink. Or eat inside on upscale dining set and still enjoy the million dollar... View all property information
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    Cudjoe Key, Florida Keys 33042