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.

Holiday Rentals with Pools in Long Key

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
    $245 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Long Key are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 18
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
    other traveller has booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 24
    4.5 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Cozy, canalfront, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bedrooms are located in a separated, quiet part of the house, while the living, dining, and kitchen are open for enjoying each... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware. All you need to bring is your clothes, bathing suit, fishing gear and... View all property information
    Location Information
    Long Key, Florida Keys 33001
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Internet Access
    • Sauna
    • Ocean Views
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware . All you need to bring is your clothes, bathing suit, fishing gear and... View all property information
    Location Information
    Long Key, Florida Keys 33001
    1 / 9
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large... View all property information
    Location Information
    Long Key, Florida Keys 33036
    We couldn't find properties that match all your filter selections. View all properties below, or reset your filters
    1 / 23
    4.5 of 5 bubbles (12) 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
    • x
    • Smoking allowed
    • ?
    About this property
    Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside.  This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room.  The complex has 2 tennis courts, weight room, dockage, pool, fish cleaning station,... View all property information
    Location Information
    Long Key, Florida Keys 33036
    5 of 5 bubbles Reviewed 1 May 2016
    There is no beach but the pool is not crowded. A hot tub is near-by. This unit,304A was very nicely decorated. Loounge chairs make watching TV comfortable. Kitchen pans...
    4 of 5 bubbles Reviewed 5 January 2015
    This condo was great for us...3 couples(family) each having their own bedroom..2 1/2 bathrooms ...we used the kitchen and 5 people could work together in it! The kitchen was...
    See all reviews
    1 / 10
    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 delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Near the house... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    No Match
    Show Prices
    Amenities & Details
    • Patio
    • Parking
    • Internet Access
    • Balcony
    • Grill
    • Satellite TV
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Minimum Rental: 28 Days "Sea Grape" is a serene, quaint part of paradise that the entire family will enjoy at this ultra-charming BEACH HOUSE just footsteps from the SEA. Come and stay in this adorable home located on the crystal clear Atlantic Ocean! The home has plenty of room for your whole... View all property information
    Location Information
    Long Key, Florida Keys 33036
    5 of 5 bubbles Reviewed 2 January 2016
    What a wonderful place! So comfortable and the views!!!! We were 6 people and had the best time. There is ample room, the views are unbelievable, the porch is out of this...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Patio
    • Terrace
    • Grill
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Minimum Rental: 28 Days "Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on a dead... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 42
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Internet Access
    • Waterfront
    • Grill
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Discover the very best of the Florida Keys in this charming pet-friendly rental with a dock and beach! The unique home offers the makings of a romantic getaway or intimate retreat with friends. The rental is three miles from town and a few hundred feet from the Long Key Viaduct. Located in Henry... View all property information
    Location Information
    Long Key, Florida Keys 33001
    5 of 5 bubbles Reviewed 10 November 2016
    We had our 2 children with us on this trip. (5years, and 3 years.) The beach was beautiful and the kids had a great time swimming and fishing. The house was perfect. We can not...
    See all reviews
    1 / 16
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    No Match
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Washer
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    FEELS LIKE YOU ARE LIVING RIGHT ON TOP THE WATER!!! Great View! Please take the time to read our client reviews! For reviews, rates and availability calendar go to our listing on V.R.B.O. Listing # 50672 Or email from here and I can send you the link. We supply many extras for our renters... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 45
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Waterfront
    • Grill
    • Internet Access
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Everyone wants to leave their worries behind and escape on a soothing beachfront vacation - why not make your next one something special? This top-floor Long Key condo has it all: a gorgeous white sand beach, a shared swimming pool with a swim-up bar, and an amazing selection of games and... View all property information
    Location Information
    Long Key, Florida Keys 33001
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Enjoy a getaway in one of Islamorada's most prestigious neighborhoods when you rent this three-bedroom, three-bathroom home. Located at the end of a cul-de-sac within the Port Antigua neighborhood on Lower Matecumbe Key, the home quickly enchants arriving guests with its peach-colored exterior set... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    From the minute you step foot in this luxurious condo, the water dominates your view and your activities. Oceanfront views from living room and master bedroom, 3 balconies... lush gardens, pool, palm trees, the finest sandy beach in the keys and the magnificent Atlantic Ocean are your constant... View all property information
    Location Information
    Long Key, Florida Keys 33001
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Let this picturesque 3-bedroom, 2-bathroom Islamorada vacation rental house serve as the perfect setting for your next trip to Florida! Featuring comfortable sleeping space for 8, top-notch amenities and an unrivaled location near beaches and main attractions - this alluring abode will not... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 27
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Satellite TV
    • Washer
    • Waterfront
    • Internet Access
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Slip into the beach lifestyle and leave the daily grind behind when you book your stay at this oceanfront Layton cottage. With a dock, expansive deck, and a stunning beach location, you may never want to leave. With historic roots as the home to the 1900's author, Zane Grey, and easy access to a... View all property information
    Location Information
    Long Key, Florida Keys 33001