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.

Islamorada Condos

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.
dd/mm/yyyy dd/mm/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
    €262 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Islamorada are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    Applied filters: Clear All
    We couldn't find properties that match all your filter selections. View all properties below, or reset your filters
    1 / 22
    4.5 of 5 bubbles (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    1 / 29
    5 of 5 bubbles (24) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    No Match
    Show Prices
    Payment Protection
    1 / 24
    4 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    1 / 41
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium... View all property information
    Location Information
    Islamorada, Florida Keys FL 33036
    5 of 5 bubbles Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    5 of 5 bubbles Reviewed 5 January 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and sunrise...
    See all reviews
    1 / 25
    5 of 5 bubbles (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 17 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple. Due...
    4 of 5 bubbles Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
    See all reviews
    1 / 18
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    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... No view of the ocean from our unit. 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 14 June 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 bubbles Reviewed 18 January 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 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Parking
    • Wi-Fi
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 28 November 2016
    Fantastic townhouse!! Came here to stay with a couple of friends and went fishing. It is right in the heart of Islamorada. You'll never run out of things to do, or places to eat...
    See all reviews
    1 / 7
    5 of 5 bubbles (1) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    No Match
    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
    5 of 5 bubbles Reviewed 2 weeks ago
    A beautiful place in a quiet neighborhood. Thorn is a wonderful host and the breakfast was delicious!
    See all reviews
    1 / 25
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Washer
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 10 November 2016
    Loved the home. Everything that was advertised was available and easy to use and find. Nice pool, access to the beach, and close to tons of activities. We were here for a family...
    5 of 5 bubbles Reviewed 20 April 2016
    I highly recommend this vacation rental! Very clean the pictures online are exactly what you see when you enter this beautiful home. It’s safe, convenient, well decorated...
    See all reviews
    1 / 19
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    No Match
    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 bubbles Reviewed 3 weeks ago
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    5 of 5 bubbles Reviewed 5 May 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...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    No Match
    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. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd bathroom in hallway. This... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 10 July 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 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    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
    "."
    5 of 5 bubbles Reviewed 9 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for making...
    See all reviews
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, gym, plenty of parking, secured entrances, elevator, and quiet. My condo is kept meticulously with attention to detail. Linens, towels and pool towels are included in the... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Wi-Fi
    • Grill
    • Patio
    • Shared Outdoor Pool...
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 bubbles Reviewed 1 May 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    5 of 5 bubbles Reviewed 28 March 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
    See all reviews
    1 / 19
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    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 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    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 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Get the List
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor...
    • Internet Access
    • Sauna
    • Hot Tub
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Spacious and impeccably remodeled luxury two-bedroom condo. Elegantly furnished by renowned designer. Italian ceramic flooring throughout, new gourmet kitchen with top of the line stainless steel appliances, designer bathrooms and walk-in closets. The Grand is a waterfront luxury full service... View all property information
    Location Information
    Islamorada, Florida Keys 33132
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 19
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • DVD Player
    • Terrace
    • Grill
    • Washer
    • Balcony
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Mina Bay - vacation rental with "the million dollar view"! Truly OCEANFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 12 March 2017
    We spent part of the holidays at Mina Bay! The views are stunning! Not to mention you can hear the sound of the waves from the second bedroom - very relaxing! The unit is located...
    5 of 5 bubbles Reviewed 24 January 2017
    Beautiful spacious oceanfront condo fully detailed and furnished in a gated community in Islamorada. The location is perfect and the beach is on the doorstep. Perfect for two or...
    See all reviews
    1 / 25
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails, board walks to... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 1 April 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
    See all reviews
    1 / 21
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Sauna
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax and Unwind in Your Luxuriously Renovated Condo With Oceanfront Views in the Fishing Capital of the World: Islamorada!! Beautiful Open Water Views in a Well-appointed Building That Provides Everything You Need for a Relaxing and Memorable Vacation. the Cozy Patio Invites You to Enjoy Your... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 27 October 2016
    This vacation was the perfect relaxing trip we have had in a long time. It is less than 2 hours from Miami airport, which is a beautiful drive. The condo was perfect. If I...
    See all reviews
    1 / 13
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Parking
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 9
    4.5 of 5 bubbles (4) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    No Match
    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
    3 of 5 bubbles Reviewed 18 December 2016
    Appealing features: Convenient location. The grounds were beautiful, with a little waterfall, trees, plants and interesting art around little sitting areas in the courtyard...
    5 of 5 bubbles Reviewed 26 May 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...
    See all reviews
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This unit is a duplex with 2 full Bedrooms and 2 full Baths - plus a loft in the master bedroom that sleeps an additional 2. There is also an electric EZ Bed for larger groups. Also included is a gas BBQ Grill in the back porch and use of any of the recreational items at the unit. Located in the... View all property information
    Location Information
    Islamorada, Florida Keys 34950
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 37
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Beautiful 2 bedroom 2 bath, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and this unit has ocean views. Some... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Upper Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** This water front home is located oceanside in the tropical Lower Matecumbe key, Islamorada, mile marker 73 (The Sport Fishing Capital of the World). It features a 15' wood dock and 12’ wide ramp, so you can bring your own boat and... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 27 October 2015
    This house was absolutely great! I loved that it had a dock and I was able to bring my boat with me instead of having to leave it at a marina. I stayed here for a week with a...
    See all reviews
    1 / 8
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Cottage is a bright and airy 1,250 sq ft unit with a huge... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 29
    4.5 of 5 bubbles (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 bubbles Reviewed 13 August 2016
    House was nice - except we did not feel comfortable - could not feel at ease - felt like we were being watched - paid a lot of money 😕
    5 of 5 bubbles Reviewed 22 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
    See all reviews
    1 / 22
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Beautiful 4 bedroom 4.5 bath home located in Venetian Shores.  The home has a great kitchen that opens up to the living room.  You can even play a game of pool in the room off the living room.  Upstairs there is a master suite that has a great porch that you can sit and enjoy your morning coffee... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Satellite TV
    • Parking
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Hot Tub
    • Shared Outdoor Pool...
    • Grill
    • Balcony
    • Satellite TV
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large balcony at this modern and luxurious oceanfront condo at mile marker 87. BOAT SLIP INCLUDED which can accommodate up to a 30' boat. SLEEPING ARRANGEMENTS (Sleeps 4) Master Bedroom: - King Size... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 19
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. Enjoy the sunrise or sunset... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 24 November 2016
    very neat and clean. Great location and views. Easy access to all of the Keys. Spacious nice size kitchen for cooking a meal if you feel like it. Nice location, because it's far...
    5 of 5 bubbles Reviewed 22 July 2016
    This place was in a great location, beautiful view, nicely furnished, perfect in every way. Would definitely stay next time I'm in the area!
    See all reviews
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Islamorada Oceanfront Pool home! Wake up in the morning to a gorgeous sunrise.  This home is a 3 bedroom 2 bath home with vaulted wood ceilings, decorated with a cottage feel.  The porch is perfectly shaded and overlooking the Atlantic Ocean. Relax in the heated swimming pool or swing in the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    No Match
    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
    1 / 42
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 4 bedrooms, 3 ½ baths, family room, living room, game rooms, pool/spa and bar. This home can comfortably accommodate 8-12 people with room to spare.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    • Grill
    • Washer
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the 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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 35
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2 bathroom apartment downstairs (3rd floor inaccessible to... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800 per... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 31
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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 bubbles Reviewed 25 March 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 bubbles Reviewed 5 June 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 / 20
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Hot Tub
    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. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 2 January 2017
    This condo is beautiful, clean and has great amenities (swimming pool, hot tub, tennis court and gym). Everything in the condo is first class with excellent quality of furniture...
    5 of 5 bubbles Reviewed 2 January 2017
    This condo was gorgeous and well stocked. They kept a collection of brochures for all the activities around the area in the condo. We loved swimming in the pool and fishing in...
    See all reviews