We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

House Rentals and Cottages in Islamorada, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $236 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 41
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 29
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 17
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Internet Access
    • Parking
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, 1 bath with a new leather couch that pulls out to a queen size bed. Downstairs an... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 6, 2016
    I can't say enough about our most recent vacation rental in the keys. We have been vacationing in Islamorada for years and I can definitely say this is one of the best places we...
    5 of 5 stars Reviewed September 21, 2015
    Awesome house. Modern furnishings makes this rental a standout. Being able to keep your boat here is a real plus. Fast access to the reefs for some amazing diving. The local...
    See all reviews
    1 / 9
    5 of 5 stars (3) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • DVD Player
    • Housekeeping...
    • Grill
    • Patio
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 26, 2016
    I recommend this B&B to anyone who just wants a beautiful property to relax and enjoy the company of your significant other. The staff is very attentive and accommodating and the...
    5 of 5 stars Reviewed September 9, 2015
    Enjoyed my 2 night stay. Bombay room was quiet, uniquely furnished, clean, and well-air conditioned. Refreshing pool and nice seating areas with plantings, water features, and...
    See all reviews
    1 / 22
    4.5 of 5 stars (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee... View all property information
    Location Information
    Islamorada, Florida Keys 33037
    5 of 5 stars Reviewed June 6, 2016
    Wonderful vacation nice, relaxing. I would definitely return. Charlie was very informative on where to go to eat. Locals were very nice too.
    4 of 5 stars Reviewed October 16, 2015
    What a great little spot! Was quiet and very peaceful. Clean and cozy! Had everything we needed. Will be back to Stay again soon! :)
    See all reviews
    1 / 19
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Patio
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed May 5, 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
    5 of 5 stars Reviewed April 6, 2016
    Very nice, quiet, low key place to stay. Great location, in walking distance of many restaurants. Would love to stay again in the near future!
    See all reviews
    1 / 18
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our unit is a short walk to the beach and dock... 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 private beach and a fishing/dock. The townhouse has 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed June 14, 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    5 of 5 stars Reviewed January 18, 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
    See all reviews
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This is a tropical vacation home away from home and is located in the heart of The Florida Keys. Perfect for families, couples, or a friends getaway. Our beautiful house has 3 bedrooms & 2 baths, and can sleeps 6 to 8 comfortably. It has a full kitchen with a spacious living room, plenty of... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 2 weeks ago
    We just returned from a week at this house. We had a great time, it is really well equipped, nice to have lots of beach and bath towels, huge fridge and freezer, and the laundry...
    See all reviews
    1 / 4
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Balcony
    • Shared Outdoor Pool...
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast.LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 14
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Grill
    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 8
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Located at mile marker 76 overlooking a beautiful canal leading to the Atlantic Ocean. Boat slip available for the adventurous types. Kayaks for those wanting to explore the local mangroves. Borrow a bicycle and peddle your way through the lower matecumbe via bike path. Don't forget to visit... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 31, 2016
    This is our last day of our month long stay in paradise. Our unit has been totally updated, is very clean and we are very sad to leave. Our boat is right outside our door...
    See all reviews
    1 / 5
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Outdoor Dining Area
    • Housekeeping...
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Family Vacation Rental Dwelling... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Ocean Views
    • Hot Tub
    • Waterfront
    • Washer
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. Spacious rooms and large double wide lanai with breathtaking views add to your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking, locked storage with bait freezer, bike... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby.... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. Saturday to Saturday stays preferred. For a couple with 2 kids or two couples. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! This direct oceanfront, well-cared for 5th floor corner unit... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed July 10, 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
    See all reviews
    1 / 4
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Hot Tub
    • Shared Outdoor Pool...
    • Housekeeping...
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Balcony
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    MINIMUM STAY: 29 DAYS - Available this winter! Very comfortable 50ft dock, wide canal, home located close to Tavernier Creek Channel with easy access to the Gulf and Atlantic. Great fishing, kayaking and diving. Concrete dock, fish cleaning station . 1.5 mile north of the world famous Holiday... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Get the List
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Satellite TV
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    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
    Location Information
    Islamorada, Florida Keys 33070
    1 / 7
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Housekeeping...
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 50 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Ocean Views
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    jaouoroqoaueo9quoruroqwu9euour99n9n9r9wur9ue9adouafiuaeoufasljfaof0askr;oasd-fsd4fas8/da5se/xgv5asqe-0taa8asdg=as9ufaoefauoatwouoasujfgaseuroue9rtasofuoasuaweroasufoauf0aasf5asf6asf6as6f6aseoufawi9rayweriyawiywririyseiyaweiryqwiryiweykcasdyvkshvckcaicaeiycaiyaisyaivyiseyvaifyksdhfikzhfisadkasrhisdhf... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed August 14, 2015
    My husband and I spent a fantastic week at this beautiful condo! The pictures don't do it justice! The view is spectacular. The inside is clean and nicely decorated! The owner is...
    See all reviews
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33023
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Parking
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Premier condo in Islamorada in Upper Florida Keys. Located on 12-acre property with 1,100 feet of oceanfront. Gated complex, large swimming pool, sand beach, and two tennis courts as well as boat ramp and dedicated slip. Spectacular Atlantic Ocean views. This top-floor, freshly-remodeled 2 bed 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY 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,... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 19
    5 of 5 stars (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    <b> Minimum Rental: 7 Nights </b> You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 13, 2016
    Having been acquainted with the area and having been, physically, all 'round the property, occasionally, but never in it - it was a shocking and wonderful surprise that this...
    5 of 5 stars Reviewed February 8, 2016
    A surprisingly tranquil place bearing in mind that it is positioned in its own grounds between two neighbouring resorts. The rental accomodation is the ground floor of a two...
    See all reviews
    1 / 31
    5 of 5 stars (23) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Children's Pool
    • DVD Player
    • Sauna
    • Air Conditioning
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 televisions, 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
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed May 1, 2016
    Absolutely fantastic facilities in a wonderful setting. From the time we booked this place until the time we left we had an amazing experience. The flat is really well...
    5 of 5 stars Reviewed April 29, 2016
    Absolutely loved staying here. We enjoyed the home away from home feel, and also a beautiful view of the ocean from the balcony. Very comfortable, and quiet. The owner was so...
    See all reviews
    1 / 25
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    <b> Minimum Rental: 7 Nights (Saturday to Saturday)</b> BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed March 22, 2016
    Brockhaus was exceptional! Everything we could have needed was provided and the property is fabulously maintained! It was exactly as pictured and immaculate. I was a little...
    5 of 5 stars Reviewed October 5, 2015
    We came for 10 days to celebrate my husband's 70th birthday. Wow! The views from the balcony and in three directions - all onto the water - were amazing. Gorgeous...
    See all reviews
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wonderful two story townhome in a private, gated community with all amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60 inch... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Wi-Fi
    • DVD Player
    • Grill
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map<BR><BR>Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6<BR><BR>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.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 29, 2015
    We thoroughly enjoyed our week here, with our adult children. The home is very clean and well-maintained and beautifully decorated and furnished in a tropical style. The outdoor...
    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!
    See all reviews
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Grill
    • Patio
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Outdoor...
    • Balcony
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay.<BR><BR>Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 6
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Terrace
    • Washer
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    License #: VR-215, DWE5403682 This resort style community is located at mile marker 85 in Islamorada and is situated directly on the Atlantic Ocean with fantastic views. The community is beautifully landscaped and has a large community pool (heated year-round) that overlooks the ocean! The... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Keys Kottage Villa is located in beautiful Islamorada, Florida Keys. We are on mile marker 82. Private Marina access and trailer parking available to guests. Bring your boat and or pet. We can accommodate up to 26 ft. vessels. This is a Fisherman's dream for a week of fishing. Please call for... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 31
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Affordable Venetian Shores canal home at the Mile Marker 86, Bay-side. Nice decor, recently updated with a private downstairs apartment. Two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room). Easy ocean or bay access via Snake Creek.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 10, 2015
    We had a wonderful time with the family fishing trip. The house is great, with grown sons the house is set up so everyone has privacey. The house is in a perfect location. The...
    See all reviews
    1 / 30
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 25, 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the new...
    4 of 5 stars Reviewed June 5, 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
    See all reviews
    1 / 16
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    <b> Minimum Rental: 7 Nights </b> Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed January 29, 2016
    Stayed in the cottage, 5 of us in total. Gorgeous cottage inside and out, set on a fabulous site with beautiful trees, shrubs, birds, green grass, stone paths, lots of parking...
    5 of 5 stars Reviewed May 28, 2013
    The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for...
    See all reviews
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Grill
    • Shared Outdoor Pool...
    • Patio
    • Balcony
    • Satellite TV
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    <b> Minimum Rental: 1 Month </b> Charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. You will enjoy your... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • Grill
    • Parking
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 stars Reviewed April 10, 2015
    Overall this was a good choice for our 2 week stay. We were within reasonable distance from both Key Largo and Marathon, and there were numerous attractions and activities close...
    4 of 5 stars Reviewed August 3, 2014
    Nice townhome with water view, easy drive to activities in Islamorada, Tavernier, and Key Largo. Townhome is 3 levels, lots of stairs, narrow staircases. Clean, updated, kitchen...
    See all reviews
    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Waterfront
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    <b> Minimum Rental: 7 Nights </b> Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed July 2, 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area by...
    5 of 5 stars Reviewed November 5, 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The...
    See all reviews
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Satellite TV
    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 4 weeks ago
    Each year we travel to the Keys for lobster season. This year we were very happy with our choice of accomodations. The condo is in a great location with easy access by boat to the...
    5 of 5 stars Reviewed January 5, 2016
    The Lobinskys, the owners, were responsive, informative, and extremely helpful. We traveled as a family with our two teenagers and our boat. Chris and Deanna provided options...
    See all reviews
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Grill
    • Patio
    • Washer
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Parking
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two... View all property information
    Location Information
    Islamorada, Florida Keys 33036