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Vacation Rentals in Islamorada, FL

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$99
Per Night
1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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$110
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1 / 29
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$428
Per Night
1 / 21
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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$1,700
Per Week
1 / 13
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
PLEASE DO NOT TRY TO BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry. We do not use the optional calendar feature on this listing. We are fully booked until March 28th! This is a very popular rental, so book your preferred week well in advance of peak season!... View all property information
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5 of 5 stars Reviewed November 16, 2014
We spent 4 nights. We just loved it. It is everything as advertised. The place is small, but so clean and neat and romantic. Great info in a binder that was thoughtfully prepared...
5 of 5 stars Reviewed September 8, 2014
Had a very relaxed we here with my partner just chilling out and doing very little except lying on the hammock watching the parrot fish swim by. The hosts are great friendly...
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From
$275
Per Night
1 / 27
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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From
$2,100
Per Month
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Minimum Rental: 1 Month Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen has been totally remodeled with all new cabinets and appliances. The living room furniture is brand new and there's a big flat... View all property information
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From
$71
Per Night
1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautifully remodeled top floor two bedroom condo with a Caribbean flair. Offered with all amenities. Unit faces the bayside and building is on the Atlantic Ocean. Enjoying the pool, jacuzzi or just sitting under tiki huts watching the ocean. Kayak available. Separate workout rooms for men and... View all property information
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$300
Per Night
1 / 35
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Gym
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
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5 of 5 stars Reviewed January 6, 2012
My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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From
$300
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a... View all property information
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From
$120
Per Night
1 / 25
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (16) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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5 of 5 stars Reviewed December 9, 2014
this condo is really great for two People. The Retreat is quite (allthough directly located at the overseas Highway), the condo is towards Bay and the small marina. The condos...
5 of 5 stars Reviewed August 11, 2014
My wife and I stayed a week at the Florida Bayside retreat and absolutely loved it. The condo was extremely clean and had a great view of the water. My wife and I also were...
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From
$1,500
Per Week
1 / 22
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautiful bayside condo, 3bedrooms 2baths, sleeps 6 comfortably, new sealy beds in all rooms with cable and wifi. Newly furnished and clean. Comes with 36 foot boat slip in the marina. There is a boat ramp on the property along with a brand new pool. Deep water dockage and deep channel to... View all property information
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4 of 5 stars Reviewed June 15, 2014
We spent a full week at this Futura Yacht Club rental, which we enjoyed very much. Here are the pro's and con's: Pro: Boat slip accommodated our 29 foot boat well Fresh water...
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From
$150
Per Night
1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Imagine waking to the beauty of a sunrise brimming over the aqua seas. Linger in your master suite and watch the ocean shift through a prism of aqua, blues and emerald greens. Gentle breezes waft through this two bedroom, two bath condo with comfortable appointments and an elegant sea glass... View all property information
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From
$258
Per Night
1 / 21
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Details Reviews (2) Make Inquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
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5 of 5 stars Reviewed September 2, 2014
Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
5 of 5 stars Reviewed January 24, 2014
This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the...
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From
$250
Per Night
1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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5 of 5 stars Reviewed November 16, 2014
my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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1 / 47
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Satellite TV
  • Sauna
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada,... View all property information
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2 of 5 stars Reviewed August 22, 2013
In addition to my wife's comments there is another thing a prospective renter must take into consideration: the lease agreement states that any disputes with the rental agent be...
2 of 5 stars Reviewed August 13, 2013
My husband and I recently rented this condo for a 3-night dive trip with our 2 boys, ages 17 and 19. While the condo itself was clean, the building was old and the parking lot was...
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From
$115
Per Night
1 / 6
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1 Bedroom, 1 Bathroom, Sleeps 3
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Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi is free also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas BBQ. Dockage for your boat and parking for your... View all property information
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3 of 5 stars Reviewed June 12, 2014
Location was great, quiet & relaxing. Close to shopping & restaurants. Allowed us to bring our elderly dog. Small but had everything you needed.
3 of 5 stars Reviewed April 25, 2014
You've got to like Key Islamarada because it's strictly for boaters and this place has a slip for yours. We booked it because it was one of the few rentals with handicapped...
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From
$250
Per Night
1 / 20
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Balcony
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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From
$500
Per Night
1 / 8
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4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This large 4 bedroom house sits jst 10 feet from a 116 foot dock. You are right around the corner from 4 bridges in a row where yo can get to the Ocean or Bay within a few minutes. View all property information
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5 of 5 stars Reviewed August 26, 2014
We had a great stay! Ended up renting both houses for a weekend stay. Had 15 people and 4 boats. We had a great weekend, Helen and her son Rob were very accommodating and quickly...
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From
$1,599
Per Night
1 / 33
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4 Bedrooms, 5 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen, snorkel in the backyard!!!! Seven Flat Screens and entire house wired for sound.... View all property information
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1 / 27
4 Bedrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Casa Dorado is a premier rental vacation home on Lower Matecumbe Key in Islamorada, Florida. Completely renovated in 2014, the spacious living and dining areas, four bedrooms, and three and a half bathrooms will make for a very comfortable stay during your visit to the Florida Keys. The house is... View all property information
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From
$975
Per Night
1 / 20
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two Acre Ocean Front Estate in the heart of Islamorada. Over 200 feet of ocean front with an ocean front pool with two sides in the Atlantic. A large flat beach area with a large patio at the ocean's edge. The estate has two villas, both have a full kitchen, living room, pull out sofas and... View all property information
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From
$271
Per Night
1 / 25
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
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From
$325
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a month. This helps keep the property exclusive, serene and beautifully respected--something you will truly enjoy should you decide to stay with us. . Absolutely no smoking inside the... View all property information
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From
$275
Per Month
1 / 21
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a... View all property information
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5 of 5 stars Reviewed November 18, 2014
We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our...
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From
$171
Per Night
1 / 14
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Modest home in great subdivision. Excellent, deep dockage on a wide canal with easy ocean and bay access via Snake Creek. Cool tropical breezes can be enjoyed on the screened in porch. Wirelss internet. VACATION RENTAL LICENSE: VR-009 Click Here for Map! CLICK HERE to view photos on a mobile... View all property information
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From
$279
Per Night
1 / 24
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
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From
$140
Per Night
1 / 21
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Enjoy spectacular water views from the private petite beach, large TIKI hut and boat dock at the end of the community,You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private kiddie pool,and play... View all property information
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From
$215
Per Night
1 / 7
Payment Protection
2 Bedrooms, 3 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a "home away from home" feel. The Coastal style conch cottage is located in the gated community, ocean front resort... View all property information
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From
$7,500
Per Month
1 / 10
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
****This house cannot rent for less than 28 days, due to a County Ordinance**** You fall in love with The Cottage @ Schooner Bay Estate at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is... View all property information
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5 of 5 stars Reviewed December 2, 2013
We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so...
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1 / 8
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished.... View all property information
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3 of 5 stars Reviewed November 7, 2014
The pictures of the home were pretty accurate although the canal it sits on offers no added feature, not used by anyone, no dock, swimming or view of boats. Home had bare minimum...
5 of 5 stars Reviewed July 14, 2013
The Perfect Getaway is an appropriate name for this house; it had everything needed for a perfect vacation getaway in the Keys. The pool and hot tub were great to cool off from...
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From
$12,000
Per Month
1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the... View all property information
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From
$2,975
Per Week
1 / 49
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN... View all property information
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5 of 5 stars Reviewed May 13, 2014
We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
5 of 5 stars Reviewed February 13, 2014
My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to locking...
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From
$18,000
Per Month
1 / 11
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and... View all property information
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5 of 5 stars Reviewed June 16, 2013
Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
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From
$500
Per Night
1 / 38
3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Balcony
  • Dishwasher
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  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application.... View all property information
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5 of 5 stars Reviewed May 19, 2013
This home was the perfect location for our spring break vacation. It was so central to many activities on the keys and so many wonderful restaurants. The home is very nice, a...
5 of 5 stars Reviewed January 20, 2013
I recently returned from Islamorada where the weather was low 80s and sunny every day. JoAn and Barbara were exceedingly helpful. The house was perfect for the needs of six of...
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From
$170
Per Night
1 / 26
3 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
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  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
ENTERED VACATION RENTAL MARKET: NOVEMBER 26, 2014 Welcome to SOL Y MAR SOL Y MAR offers 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. The Property is located in the Center of the Florida Keys, Tavernier, 1.5 Hours to Miami, 1.5 Hours to Key West;... View all property information
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From
$107
Per Night
1 / 15
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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  • ?
About this property
Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters,... View all property information
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5 of 5 stars Reviewed July 9, 2014
Stayed here the last week in June with my wife, two kids and granddaughter. Room was clean and well laid out but a little bit cramped for the number of people. Closet space was...
5 of 5 stars Reviewed May 26, 2014
The condo was nicer and larger than we expected. It had everything we needed plus a few surprises: beach chairs and a float, very comfortable beds, and quiet neighbors. Also...
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From
$5,000
Per Week
1 / 8
3 Bedrooms, 4 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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  • ?
About this property
VR-203 You can not rent this property for less than one week. Relax and rejuvenate at The Palms at Schooner Bay Estate. Features are a plantation-style home and beautiful wrap around porch, 3 bedrooms/3.5 baths, a beach entry pool, and abundant coquina decking. The natural landscaping enhances the... View all property information
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3 of 5 stars Reviewed April 8, 2013
The site was beautiful. Nice sized house, clean, beautiful view, well kept grounds. Really nice covered porch all around the house where you could get out of the sun and enjoy...
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From
$6,500
Per Week
1 / 14
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
VR-202 You can not rent this property for less than one week. The Gardens is a 4/4 private home surrounded by impeccably landscaped grounds. This property has over 50 types of palms, abundant orchids, and bougainvilleas. At your doorstep is a breathtaking view of the Atlantic Ocean where you can... View all property information
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From
$22,000
Per Month
1 / 15
5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean... View all property information
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1 / 15
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully... View all property information
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From
$6,000
Per Week
1 / 22
5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Village Permit # VR-204 You can not rent this property for less than one week. Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean….and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres... View all property information
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From
$640
Per Night
1 / 11
5 Bedrooms, 4 Bathrooms, Sleeps 9
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room... View all property information
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From
$385
Per Night
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three... View all property information
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5 of 5 stars Reviewed May 12, 2014
We loved staying at Villa Marlin, and the owner was very helpful before and during our stay. The home is prettier than the pictures, and we felt right at home!
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From
$300
Per Night
1 / 29
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich... View all property information
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5 of 5 stars Reviewed August 20, 2014
We fell in love with the villa the minute we walked in through the door. Everything was immaculate and extremely welcoming. The owner had thought about everything and the box of...
5 of 5 stars Reviewed June 30, 2014
This was the perfect place for a relaxing vacation with my extended family. The location was great, and close to all Islamorada has to offer. The pool was so nice, overlooking the...
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1 / 9
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This comfortable, country-style cottage is located in Plantation Key Colony, a quiet family neighborhood at mile marker 90, bayside, on Plantation Key, the northernmost key of the seven keys that comprise Islamorada, "The Village Of Islands". It is a three bedroom, three bath home: the master... View all property information
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From
$800
Per Night
1 / 45
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
* 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
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From
$1,500
Per Night
1 / 15
3 Bedrooms, 3 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Royal Palm, South - Ocean Front Home Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil Sena —with nothing compromised— this luxurious Caribbean home is on the ocean's edge with 180 degrees of unobstructed ocean views and sunrises. Complete privacy. Full... View all property information
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From
$185
Per Night
1 / 6
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a... View all property information
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5 of 5 stars Reviewed November 18, 2014
Just wanted to thank Bill for a wonderful four days at his place. Condo has tremendous views -- you are on the top floor -- amenities are great as well as the sleeping...
4 of 5 stars Reviewed July 7, 2014
The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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From
$850
Per Night
1 / 7
Payment Protection
8 Bedrooms, 6 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Keys Oceanfront Estate The Florida Keys largest and most presteges home A peaceful and picturesque mansion awaits you and your loved ones in Islamorada, Florida. Grab your rod and reel, for an afternoon of casting right off the dock. Enjoy the abundance of nature right outside your door while you... View all property information
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5 of 5 stars Reviewed March 26, 2014
The house was amazing! Just as the pictures show. We were traveling with 4 adults and 6 teenagers. There was always something for everyone to do. The property manager was friendly...
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From
$100
Per Night
1 / 6
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Call Property Manager for Best Rate. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool sandy Beachfront, fishing pier with flats boat dockage (drawing 24' or less) located directly on the ocean your views could NOT be any better. Under the condo... View all property information
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