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.

Vacation Rentals 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.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 22 Rentals in Summerland Key
    loading...
    Travelers to Summerland Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 15
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    From
    $1,250
    / Night
    Payment Protection
    View Details
    1 / 18
    3 Bedrooms / 10 Bathrooms / Sleeps 8
    Overview Make Inquiry
    From
    $285
    / Night
    Payment Protection
    View Details
    1 / 30
    2 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    From
    $5,988
    / Month
    View Details
    1 / 8
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Internet Access
    • TV
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    5 of 5 stars Reviewed June 9, 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 April 2, 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
    From
    $20,000
    / Month
    View Details
    1 / 9
    7 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Waterfront
    • Washer
    • Satellite TV
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located 25 miles from Key West, this unique estate property has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon fishing, lobstering and privacy. This newly constructed estate just completed in July 2009 is located on 1 acre adjacent to wild life reserve... View all property information
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    From
    $329
    / Night
    View Details
    1 / 8
    5 of 5 stars (1) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Waterfront
    • Hot Tub
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    5 of 5 stars Reviewed November 10, 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
    From
    $170
    / Night
    View Details
    1 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Deck
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    4 of 5 stars Reviewed April 27, 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
    From
    $125
    / Night
    View Details
    1 / 15
    3 of 5 stars (3) Average
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Waterfront
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    'The Pisces House' is a cozy cottage perfectly located on a deep water canal with open water views. This adorable 'keys style' cottage has everything you need for a relaxing getaway. This 1 bedroom/2bath cottage features a FULL kitchen, quaint living quarters with a sofa bed, and a peaceful patio... View all property information
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    1 of 5 stars Reviewed June 18, 2015
    We booked this rental after seeing the the review off tripadvisor so thought it would be o k , but when we arrived our hearts sank . The house is in serious state of disrepair the...
    5 of 5 stars Reviewed June 1, 2015
    We stayed for 9 nights. Marianne was easy to communicate with prior to our arrival. In addition, she provided a cell phone contact in case there were any issues. We arrived at 4PM...
    See all reviews
    From
    $2,400
    / Month
    View Details
    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Porch
    • Dishwasher
    • Air Conditioning
    • Linens Provided
    • TV
    • Internet Access
    • DVD Player
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $5,500
    / Month
    View Details
    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Porch
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Dishwasher
    • Linens Provided
    • TV
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $393
    / Night
    View Details
    1 / 3
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Boat Available
    • Water Views
    • Satellite TV
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    From
    $250
    / Night
    View Details
    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Stereo System
    • Waterfront
    • Satellite TV
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    From
    $364
    / Night
    View Details
    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Waterfront
    • Dryer
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys 33042
    From
    $13,500
    / Month
    View Details
    1 / 22
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • TV
    • Porch
    • Water Views
    • Internet Access
    • Waterfront
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A tranquil oasis is your destination at?Ocean Magic, with tropical Caribbean waters right out your door. This estate quality home offers all the benefits of your own private country club. When entering the gated driveway beautiful gardens abound. Guest cottage consists of 1 bed/1 bath, kitchenette... View all property information
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $7,500
    / Month
    View Details
    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Linens Provided
    • Air Conditioning
    • TV
    • Internet Access
    • Porch
    • Water Views
    • Dishwasher
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $4,800
    / Month
    View Details
    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Porch
    • DVD Player
    • TV
    • Water Views
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $6,900
    / Month
    View Details
    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • TV
    • DVD Player
    • Water Views
    • Porch
    • Internet Access
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Surrounded by lush, tropical landscaping, this gated open-water vacation home comes equipped will all the thoughtful touches of home and so much more. Choose the fantastic top floor master bedroom with Jacuzzi tub and sitting room or one of the other fantastic rooms! Enjoy spectacular ocean views... View all property information
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $6,000
    / Month
    View Details
    1 / 7
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Porch
    • Internet Access
    • Water Views
    • Waterfront
    • Air Conditioning
    • TV
    • DVD Player
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $3,300
    / Month
    View Details
    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Dishwasher
    • Porch
    • Air Conditioning
    • Internet Access
    • Linens Provided
    • TV
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $2,750
    / Month
    View Details
    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • TV
    • Linens Provided
    • Porch
    • Microwave
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $7,000
    / Month
    View Details
    1 / 10
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Porch
    • TV
    • Linens Provided
    • Water Views
    • Waterfront
    • Air Conditioning
    • Dishwasher
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys
    From
    $6,000
    / Month
    View Details
    1 / 12
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Linens Provided
    • TV
    • Water Views
    • Internet Access
    • Porch
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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? Flat screen Sony 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
    Make Inquiry
    Location Information
    Summerland Key, Lower Keys