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 and Apartments in Summerland Key, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
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
    $251 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Summerland Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 20
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    1 / 18
    3 Bedrooms, 10 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Parking
    • DVD Player
    • Satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy this large oceanfront home on Summerland Beach. This expansive 3 bedroom, 2 bathroom home is just perfect for large families and big boats. Over 2,500 square feet of living space with lots of room for everyone to spread out. The kitchen has plenty of room for everyone to get in act to make... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Step away from the norm and into the most peaceful and quiet blue waters you will ever see, within the Private Island of Serenity, located just 25 miles from Key West and a short boat trip from Summerland Key. This three bedroom home boasts almost 360 degrees of waterfront views from its glass... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 8
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Washer
    • Private Outdoor...
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open.. This is a spacious oceanfront 4/2 home with a heated pool/spa and breathtaking open water views! It is located on beautiful Ramrod Key 110 ft concrete... View all property information
    Location Information
    Summerland Key, Lower Keys
    5 of 5 stars Reviewed 10 November 2014
    This oceanfront home in Ramrod Key is beautiful! It is clean and well kept. The owner ensures that you are comfortable in your home away from home. The view is gorgeous. The...
    See all reviews
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home has three stories including a super play room off the pool area with a ping-pong table and a big screen TV for the kids. The 2nd floor accommodates a large... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Balcony
    • Patio
    • Washer
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    3 Bedroom / 2 Bath Upstairs 1 King Bed, 2 Queen Spacious office with open water views 2 Bedroom/ 1 Bath Down 1 King, 2 twin 2 Separate living room areas, up and down, each with large flat screen TV's and DVD players Large screened porch up and down Heated Pool w/ outdoor shower and pergola... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 14
    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Porch
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Need some Florida therapy? This is just what the doctor ordered at Group Therapy. Soak up some Florida  keys sunshine, float around in the great pool or jump in the boat and off you go to explore the excellent fishing and diving the keys have to offer. The home just decorated in beach style motif... View all property information
    Location Information
    Summerland Key, Lower Keys
    4 of 5 stars Reviewed 18 February 2016
    My husband and I had a long planned Feb 2016 trip planned to the Lower FL Keys. Upon arrival the VRBO house we had rented became unavailable. I called Action Keys Realty on...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Waterfront
    • Grill
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome Tropical Villa which is a large home on a clear, flow through swimming canal. With 65 feet of seawall, and 4.5 feet of control depth, even large sailboats can be accommodated here! We only three minutes to the ocean, only fifteen minutes to Looe Key reef (one of the Key's premier dive... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Just imagine...Balmy southeast winds are blowing with a perfect Florida Keys sunset right in front of you, while relaxing in your comfy lawn chair with a frozen margarita. This could be you if you choose Ocean Breeze for your next Florida Keys adventure. Located on Summerland Key directly on the... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42" Sony flat-screen, hi-def TV with surround sound makes you feel like you are right in the middle of the action. Kitchen is a chef's delight with... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining areas for friends and family.... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys. This stylish home is outfitted in Florida tropical style with cool and comfortable leather in the... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    The open porch catches the breeze and sun with this Florida Keys vacation rental! Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all the comforts of home. This tropical setting will set your mind at ease in a true, Florida Keys style. The... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This lovely 2 bedroom, 2 bath residence is located on Summerland Key at mile marker 24 just north of Key West for sightseeing, great restaurants or just take in the color of the local history in our southernmost most city. The home is comfortably furnished in tropical colors. Open kitchen, dining... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 8
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Washer
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Lovely three Bedroom/2 Bath home with pool and hot tub located on Summerland Key. Mile marker 25. Deep water swimming canal with boat ramp and dockage. Large screened in porch for outdoor dining and BBQ grill. Tropical landscape and extra sleeping. Sleeps up to 8. 28 day rental. Please... View all property information
    Location Information
    Summerland Key, Lower Keys
    5 of 5 stars Reviewed 9 June 2015
    Island Living is quite comfortable for us. Plenty of room for friends. Quiet, safe neighborhood. Easy ride to shopping and Key West. The pool is very nice. Boating access is...
    4 of 5 stars Reviewed 2 April 2012
    The home and pool were clean, comfortable and nicely furnished. Kitchen is simply furnished and could use a variety of serving dishes and sharp knives. You will need to purchase...
    See all reviews
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Porch
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef's dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops. The... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Porch
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key where astounding sunsets and ocean vistas will be yours. The grounds are very shady and groomed with a nice Tiki hut at the waters edge. Plenty of dockage on the canal side and... View all property information
    Location Information
    Summerland Key, Lower Keys
    Get the List
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Summerland Place is just what the doctor ordered. Fabulous weather, boating and diving every day plus a sweet place to call home. Located at mile marker 25 with some of the best boating access in the area. The main level has 2 bedrooms, a bathroom, kitchen and living room. Decorated in Keys style... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 11
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Seasonal Rates Start at 1190.00 per week based on 7 night miniimum stay. Extremely private two bedroom two full bathrooms on beautiful Little Torch Key , Oceanside . Deep Water swimming canal . Plenty of room for docking and parking of trailers etc... house was completely renovated less than... View all property information
    Location Information
    Summerland Key, Lower Keys
    5 of 5 stars Reviewed 10 April 2016
    Down from NJ. This is a nice,clean,well equipped house. Located close to Winn-Dixie, bait shop, fuel dock and ramp. Key West is a half hour away. Friendly neighbors. My dog and...
    4 of 5 stars Reviewed 28 April 2015
    There was plenty of parking for our truck and boat trailer. We liked the fact that the boat dock was inset for more protection of the boat, but parking into it was a little...
    See all reviews
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • DVD Player
    • Porch
    • Air Conditioning
    • Washer
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This is a spacious, open floor plan, Three bedrooms, Two Bathrooms, 6 people accomodation, brightly painted colors, beautifully furnished. Relax in the upper covered porch or down below to the open and spacious patio leading to the pool. Outdoor Tiki shower hut. The grounds are landscaped with an... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing. The shady screened porch overlooks the... View all property information
    Location Information
    Summerland Key, Lower Keys
    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Big Torch Key is reminiscent of the Florida Keys 40 years ago,seclusion and peace invade your senses immediately, sunset views that will take your breath away. Torchview has an open floor plan (kitchen/living room/dining room) with a huge master suite(king bed)and two other bedrooms (one with a... View all property information
    Location Information
    Summerland Key, Lower Keys
    5 of 5 stars Reviewed 11 February 2016
    This is the best vacation rental we have ever been to. It is beautifully decorated, very clean, and the owners go above and beyond to ensure you have an amazing experience.
    See all reviews