Summerland Key Florida Vacation Rentals


Summerland Key Vacation Rentals, Condos and Short Term Rental Accommodations

Book our vacation rentals with selection of 1,2,3 or 4 bedroom homes in Summerland Key Florida. Search hundreds of properties, find the best deal when you book directly online.

Cove Isles 0
Vacation Home Rentals - Summerland Key
2 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $3,300.00/Mo
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 ... read more »
Big Torch Retreat 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $3,000.00/Mo
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 furnishi... read more »
Barbados Isle 0
Vacation Home Rentals - Summerland Key
Studio -  Sleeps:
Starting at: $3,350.00/Mo
Ready for some fun in the sun? This Ramrod Key vacation home is the perfect spot! This home is located at milemarker 27 in Breezeswpt Beach Estates. Spend some fun time at the Looe Key Reef Resort Tiki bar just a mile away where you can sip on s... read more »
Caribbean Dream 0
Vacation Home Rentals - Summerland Key
4 Bedroom(s) 3.0 Bath  Sleeps: 8
Starting at: $6,000.00/Mo
This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. We added terrific views to make this the perfect setting for your next vacation in Paradise! Ice machine, bait freezer, do... read more »
Coral House 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $3,350.00/Mo
The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer. This home is beautifully deco... read more »
Owl's Nest 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $3,600.00/Mo
Key West / Big Pine Key / Marathon... read more »
Margarita Villa 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $4,200.00/Mo
Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys! Just imagine yourself gazing out at these spectacular ocean vistas! The entire water-side of t... read more »
Chickies Conch Cottage 0
Vacation Home Rentals - Summerland Key
2 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $2,800.00/Mo
Delightful and comfortable Florida Conch-style Cottage on Little Torch Key. Enjoy the beautiful, open-water views over Pine Channel with incredible sunrises and moon rises. The interior of this home has been beautifully updated with new kitchen, i... read more »
Keys Escape 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 3.0 Bath  Sleeps: 6
Starting at: $5,400.00/Mo
Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for fr... read more »
Galleon Bay 0
Vacation Home Rentals - Summerland Key
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,700.00/Mo
Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Key... read more »
Casa Turquesa 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $6,200.00/Mo
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 tropi... read more »
Blue Lagoon 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $5,900.00/Mo
Looking for that perfect vacation spot in the Keys? This is the one. 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-d... read more »
Casa Caribe 0
Vacation Home Rentals - Summerland Key
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,500.00/Mo
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 ... read more »
Gulf Shores 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $3,000.00/Mo
Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all the comforts of home. The open porch catches the breeze and sun. This tropical setting will set your mind at ease.The canal provides qui... read more »
Cayo Villa 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 3.0 Bath  Sleeps: 6
Starting at: $8,000.00/Mo
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... read more »
Bow Channel Manor 0
Vacation Home Rentals - Summerland Key
3 Bedroom(s) 3.0 Bath  Sleeps: 6
Starting at: $5,450.00/Mo
Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key. The grounds are lik... read more »
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