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.

Matecumbe Key House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$363 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Matecumbe Key area vacation rental. You're so close to securing your perfect getaway. Book today.
    158 Matching Rentals in the Matecumbe Key AreaView all 296 rentals
    Sort by:
    Default
    75130 Overseas Highway1 / 19
    (5)Excellent
    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    75731 Overseas Highway1 / 32
    (13)Very good
    Matecumbe Key
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Matecumbe Key
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Cable/satellite TV
    • Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days  'Crystal Clear Bay Home' offers beautiful open water views and fabulous world famous sunsets. This brand new home is located at Mile Marker 89 on a quiet street in Islamorada. Everything is brand new and offers 4 bedrooms and 2 1/2 bathrooms. Upstairs,on the main level...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Matecumbe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on the beautiful Florida Bay, this 3BR/2BA Islamorada home offers an idyllic waterfront haven with its own private beach, dock, kayak, paddleboards, and sprawling backyard with a volleyball net. Spend leisurely afternoons fishing off the dock before cooking up your catch on the grill....
    View all property information
    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Matecumbe Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a sun-soaked day, head back to your canal-front 4BR/3BA home and take a refreshing dip in the sparkling private pool. Fire up the BBQ for an al fresco feast on the covered patio. As the stars come out, go for a soak in the private hot tub. A full wraparound balcony, cool tile floors, and...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    The following rentals are within 10 kilometres of Matecumbe Key.
    Escape to Paradise in a Gated Tropical Bayfront Estate (Free Wifi)1 / 19
    (3)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 2018
    Loved the cottage, we had such a nice time staying here. It's a great Location, near a lot of nice restaurants and there is great snorkeling and kayaking nearby. Had a BBQ every...
    Reviewed 14 June 2017
    The best part about this rental is the bayside snorkeling and the fact that 2 double kayaks are included with the rental. You can kayak across the bay to the mangroves. The best...
    See all reviews
    About this property
    Tucked away on a gated tropical estate, is our 'Island Breeze Cottage'. This cottage is located in the middle of the Estate and steps away from our white sandy beach and those beautiful Gulf of Mexico sunsets !! There is a tiki hut on the beach. And a dock to fish from or go snorkeling right from...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Moon Bay A2041 / 33
    (1)Very good
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This condo was a perfect location for our vacation. Restaurants, shopping and parks close by. The most beautiful sunsets I have ever seen.
    See all reviews
    About this property
    Want to be close to the Mainland while still being in the Upper Keys? Look no further. This beautifully decorated condo at Moon Bay will not disappoint. The Master bedroom has a spacious King size bed. Guest bedroom has 2 twin beds and there is a bonus room with a trundle bed. Vibrant colors...
    View all property information
    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
    See all reviews
    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
    View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage is located in a Gated Estate on the Gulf of Mexico in the Florida Keys for watching those beautiful Keys Sunsets !!! 'Tiki Palm Cottage' has it's own private Tiki hut for relaxing with a cool beverage or just for reading a favorite novel. Walk in through double French doors to a large...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Matecumbe Key rentals sent straight to your email!
    Get the List
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated and remodeled 2 Bedroom Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' This unit is comfortably and stylishly furnished, it has(2)...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Florida Keys Splendor at Hammer Point1 / 24
    (14)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2016
    I would recommend staying here it was a very comfortable home in a great location close to everything sunsets were beautiful and (5) manatees came to visit twice a day right off...
    Reviewed 18 December 2015
    We stayed here for three nights in December. Migdy is the best. Manatees visited us at the dock. All conveniences of home are here.Nice restaurants in the area, but the house...
    See all reviews
    About this property
    If you want peace and quiet and disconnect from the daily stresses of life, this is the place to be! Come enjoy all that the Florida Keys has to offer in this 'home away from home' Your reservation includes so many amenities! Great for a well-deserved get-away or Mini-vacation! Located in the...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    THE PERFECT GETAWAY1 / 28
    (6)Very good
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2016
    My husband and I searched for six weeks to find the perfect house for our vacation with another couple, and kept coming back to this one. All four of us were looking for a...
    Reviewed 9 April 2016
    We thoroughly enjoyed staying at the Perfect Getaway. My family and I had enough space to sleep, relax and enjoy meals together. The pool was a great addition to the property...
    See all reviews
    About this property
    This four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. It is situated in a clean, upscale neighborhood of all waterfront homes. The house is equipped with all the comforts of home. It is modernly furnished. Upstairs there are...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tropically decorated 2 bedroom 2 bath unit, has a King bed and (2) Twins beds is approximately 1 hour and 20 minutes from Miami International Airport and 90 Minutes from Ft. Lauderdale airport.  Futura Yacht Club is located in the Village of Islamorada in the Upper Florida Keys. Located...
    View all property information
    Location Information
    Tavernier, Key Largo 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3/2 or 6/4 Tropical Parroteyes, Location,Comfort Views!1 / 27
    (1)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
    See all reviews
    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. You Can Rent One Level a 3/2...
    View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed 24 August 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
    See all reviews
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Water front Boat slip for 20-22 foot Jacuzzi Tiki hut Close to pennecamp park , winndixie , restaurants , all water sport activities and rentals . Good weather year round . Enjoy beaches , fishing access to ocean and bayside . Restaurants accessible via bay and Oceanside . Great for relaxation
    View all property information
    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    **Spring Discount** Amazing views from this Oceanside Home near Pennekamp, dinin1 / 24
    (3)Very good
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Parking
    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    Here is the bottom line..after about a week of our two month rental we had already rented this home for next year. The location is awesome and fishing off the dock was...
    Reviewed 25 March 2015
    Great House! Big enough for extended family. I really enjoyed the dock and the view of the water. Clean and neat.
    See all reviews
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MM 90 Beautifully Remodeled Home. This charming home is surrounded by mature trees making it very private, beautifully updated, offering 2 bedrooms 1.5 bathrooms (split floor plan), awesome screened in porch, car port, tons of storage, large kitchen pantry, balcony off from the main bedroom while...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Islamorada Waterfront Paradise 21 / 29
    (5)Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a dip in our gorgeous new pool, or Jacuzzi (for 14 people)! Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private gatehouse and road. The suite offers a...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    82754 Overseas Highway1 / 29
    (4)Excellent
    Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed 9 May 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
    See all reviews
    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 1 Bedroom 1 Bath Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' The unit offers sea breezes and ocean views. Seagulls condo offers a...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    **Spring Discount** Ocean Front Keys Home with Private Beach - Great for Kite Su1 / 25
    (2)Average
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
    See all reviews
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    **Spring Discount** Family Friendly Executive Bay Townhome with Beach & Pool1 / 25
    (10)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Tavernier family vacation home is like 'home away from home'. Property is fenced. Nicely decorated and tiled throughout our home is very well kept and clean only four homes from open Bay access with clear water canal and direct ocean access via Tavernier Creek. Master bedroom features queen...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    132 Columbus Drive1 / 18
    (16)Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
    See all reviews
    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Islamorada
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Blue Marlin House, Anglers Reef Islamorada1 / 23
    (1)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 BR 2 BA 1 HF BA Sleeps 8 There is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    107 San Remo Drive1 / 36
    (1)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2018
    What a fabulous area and home, Nancy and Norm were (the owners) told us places for dining out, Island times grill, Craigs seafood ( Mahi Mahi sandwich is to die for) Mrs Mac...
    See all reviews
    About this property
    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs.  The downstairs apartment has a complete kitchen and living room and separate bedroom.   There is a screened in porch of the living room upstairs.  The home has awesome...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the...
    View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Islamorada
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at SuCasa next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. This 2-bedroom apartment sleeps four comfortably in two bedrooms each with a queen-sized. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee maker, blender and all the...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweet little home away from home. This 2 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 4th floor balcony. If you are looking to get out on the water the condo...
    View all property information
    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    PALMS 3091 / 25
    (1)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    Our three month stay was excellent. We enjoyed the location and close proximity to where we had our boat stored.
    See all reviews
    About this property
    Minimum Rental: 28 Days 'The Palms #309' is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (4)Excellent
    Islamorada
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
    Reviewed 12 February 2017
    On our recent family trip to the keys, we were lucky enough to find this amazing home. We stayed for one week and wish we had stayed a month!The house is 6 stars and the hosts...
    See all reviews
    About this property
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a waterfront manufactured home that has been upgraded. You can rent the home with or without the boat. You can relax in the waterfront Tiki hut or float in the pool. The house is very convenient to either the ocean or bay side of the island. House comes complete with cable tv in every...
    View all property information
    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'The Beach Fixes Everything'. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid 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...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    MANATEE MANOR1 / 25
    (2)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Internet Access
    • Patio
    • Parking
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    We enjoyed the month of June at Manatee Manor. You are greeted on the first floor with a comfortable game room area that includes a pool table that converts to ping pong and...
    Reviewed 10 August 2017
    Our family stayed and Manatee Manor for the month of July and had the perfect summer vacation. The layout of the home as well as the quality of the furnishings, location and...
    See all reviews
    About this property
    Minimum Rental: 28 Days 'Manatee Manor' is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier Creek...
    View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    MY PARADISE1 / 25
    (3)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Balcony
    • Internet Access
    • Parking
    • Patio
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Just returned from our 2nd annual monthly stay at My Paradise. We again had a wonderful stay. The house is right on a beautiful sandy beach and is great for walking and...
    Reviewed 3 October 2016
    The house is a dream! It is located in a quiet dead-end road and right on the sandy beach.Perfect for a family vacation. The house is fully equipped, from the kitchen to...
    See all reviews
    About this property
    Minimum Rental: 28 Days 'My Paradise' is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    We spent a wonderful, spirit rejuvenating MONTH with Ewa and Peter at their beautiful home by a lagoon in Lower Matecumbe Key. At first we bustled about, kayaking from the dock...
    Reviewed 1 March 2016
    We had a delightful stay in this lovely property - by the water and with hammocks and a very peaceful setting. The room was well equipped and the owner were very helpful.
    See all reviews
    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    1
    List your property
    Owner log in