Summerland Key Rentals
From $295 per night (USD)VRBO
FL Keys Cottage with Ocean Views - Venture Out Unit 395
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Island Oasis! Tropical Breezes Across from the Marina! A perfect oasis with beautiful views all day, every day. ...
From $295 per night (USD)VRBO
From $647 per night (USD)Expedia
NAUTILUS...ocean front cottage retreat ~
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nautilus... ocean front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll nee ...
From $647 per night (USD)Expedia
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One bedroom One bathroom sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Venture Out a real nice and secure gated community with a pool , hot tub Pickleball courts , tennis courts , marina wit ...
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From $343 per night (USD)Expedia
COZY CLEAN on CANAL - Venture Out Unit 342
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VO342 35' Dockage Lovely Canal Views Covered Porch Walk to Amenities! This beautifully decorated vacation home is locate ...
From $343 per night (USD)Expedia
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Key house on canal 5-minutes to ocean with 75’ of dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This rustic home offers open beamed ceilings and peek-a-boo views of the ocean from the top living area. Complete with 7 ...
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From $279 per night (USD)Expedia
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1Bd/1Ba Highrise Unit Located in a gated community, just 20 miles from Key West, this cottage is the perfect place if y ...
From $279 per night (USD)Expedia
From $375 per night (USD)VRBO
Open Water Views - Venture Out Unit 373
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO373 Ocean Views 35' Dockage Located in the Marina Basin If you are looking for a great location this 2 Bedroom / 2 Bat ...
From $375 per night (USD)VRBO
From $232 per night (USD)Expedia
ISLAND PARADISE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We have central air,1 bedroom, 1 bathroom with fully stocked kitchen, washer and dryer, dishwasher, toaster, keurig duo ...
From $232 per night (USD)Expedia
From $375 per night (USD)VRBO
Amazing Open Water Views - Venture Out Unit #374
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO374 Ocean Views 35' Dockage Located in the Marina Basin If you are looking for a great location this 2 Bedroom / 2 Bat ...
From $375 per night (USD)VRBO
From $746 per night (USD)Expedia
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO093 OCEANFRONT GEM! TRUE SOUTHERN EXPOSURE STILT 2BD/2BA 35' SEAWALL Enjoy breathtaking panoramic ocean views from th ...
From $746 per night (USD)Expedia
From $266 per night (USD)VRBO
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come vacation in this cozy two bedroom with one bath home. The home has been recently renovated. Just added a non touch ...
From $266 per night (USD)VRBO
From $275 per night (USD)Expedia
Waterfront house conveniently located.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
From here you can enjoy all that the Keys have to offer. Conveniently located at the 23 mile marker. Walk to Square G ...
From $275 per night (USD)Expedia
From $625 per night (USD)VRBO
Open Water ~ Pool Home in Summerland Key
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Prime Oceanfront Tropical Gem & The Ultimate in Luxury Waterfront Living! Florida Keys luxury deep water oceanfront pool ...
From $625 per night (USD)VRBO
From $250 per night (USD)Expedia
Catch n' Relax in the Keys!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing waterfront property with 17' seawall. Two bedrooms, 1.5 bathrooms and a fully stocked kitchen for everything you ...
From $250 per night (USD)Expedia
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Tropical Island Getaway! - Venture Out #653
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VO653 Tropical Island Paradise! Walk to Pool and Activities! Charming 1 bedroom with full standard size bathroom, spaci ...
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From $304 per night (USD)Expedia
3 night minimum! Spectacular Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3 Nite Minimum Stay! Spectacular Ocean Views! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** Newly renovated 2 be ...
From $304 per night (USD)Expedia
From $235 per night (USD)VRBO
Sea Breeze Cottage - Venture Out Unit 066
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sea Breeze Cottage VO066 2Bd/2Ba South End of Park Walk to Ocean! This delightful 2 bedroom, 2 bathroom cottage sleeps ...
From $235 per night (USD)VRBO
From $310 per night (USD)Expedia
Mile Marker Mahi - Venture Out #465
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mile Marker Mahi 2Bd/2Ba 35' Boat Dockage Open Water Views A sun seeker's haven, and a fisherman's paradise, this quain ...
From $310 per night (USD)Expedia
From $260 per night (USD)VRBO
Walk to the Pool - Venture Out Unit 333
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO333 70' Seawall 2Bd/1.5Ba Large Covered Porch Lovely 2Bd/1.5Ba vacation home in desirable boating community only 15 m ...
From $260 per night (USD)VRBO
From $484 per night (USD)Expedia
House of the Rising Sun - VO479
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VO479 Spectacular Oceanfront Panoramic Views! 55' Seawall w/ Whips- A Boater's Paradise!Enjoy breathtaking panoramic oce ...
From $484 per night (USD)Expedia
From $714 per night (USD)VRBO
Newly Renovated Ocean Estate- Relax and enjoy this magnifecent
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Magnificent Ocean Front Estate! Enjoy breathtaking views of the ocean from the large screened in porch. Prepare freshly ...
From $714 per night (USD)VRBO
From $550 per night (USD)Expedia
Ocean Front - Private 56' Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VO095 Spectacular Oceanfront Panoramic Views 56' Seawall Boaters Paradise! $150 additional discount given at booking for ...
From $550 per night (USD)Expedia
From $195 per night (USD)VRBO
Relaxing Home in gated community
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 2 bedroom, one bath home is located in Venture Out on Cudjoe Key, FL. 23 miles outside of Key West!. Venture Out i ...
From $195 per night (USD)VRBO
From $367 per night (USD)VRBO
Reel Caribbean Getaway | 4 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Fantastic deep-water boating from this spacious, gated, 4 bedroom / 2.5 bath home on Summerland Key's Caribbean Drive Ea ...
From $367 per night (USD)VRBO
From $205 per night (USD)VRBO
Waterfront Relaxation and Barefoot Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Pack your bags and bring your boat! This home is located on the canal with easy access to the Gulf and Atlantic. It is e ...
From $205 per night (USD)VRBO
From $156 per night (USD)VRBO
Waterfront beach house with boat ramp
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront home with private boat ramp. Cozy remodeled 2 bedroom 2 bath (plus bonus room and outdoor shower). Enjoy bik ...
From $156 per night (USD)VRBO
From $450 per night (USD)VRBO
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy ...
From $450 per night (USD)VRBO
From $197 per night (USD)Expedia
Relaxing and Inviting home in gated community
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in ta ...
From $197 per night (USD)Expedia
From $310 per night (USD)VRBO
Keys Time - Unit 437 Venture Out 2Bed\/2Bath Canal Front Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Keys Time!! Slow it down. Unwind. Enjoy the Island Life! This Beautifully furnished 2 bedroom 2 bath canal ...
From $310 per night (USD)VRBO
From $70 per night (USD)Expedia
RV resort site\/rvsite\/spot\/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT 25%
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
RV RESORT SPOT. BIG Rig Friendly 25% discount per month RV RESORT SITE 25% DISCOUNT PER MONTHLY rental /CAMPSI ...
From $70 per night (USD)Expedia
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Crab Shack
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This cozy home on Cudjoe is exactly what you are looking for if you want good boating. The canal it is on opens up to Ke ...
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From $285 per night (USD)VRBO
Spectacular Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape completely in this open and airy 3 bedroom 2 bath oceanfront home. Situated on the northern shore of Sarcarma Bay ...
From $285 per night (USD)VRBO
From $500 per night (USD)VRBO
3 Bedroom 3 Bath Pool Home with Gorgeous Atlantic Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the Prestigious neighborhood of Summerland Key Isles!! This gorgeous 3 bedroom 3 bath property has one of the ...
From $500 per night (USD)VRBO
From $215 per night (USD)VRBO
Beautiful 3 bed 2 bath deep water canal front home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom 2 bath canal front home on Summerland Key. This home features deep water dockage, great access to th ...
From $215 per night (USD)VRBO
From $283 per night (USD)VRBO
Pelican's Paradise - Unit 507 Venture Out 1 Bedroom\/1 Bath Canal Front Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to Pelican's Paradise, a charming one-bedroom, one-bath cottage nestled in the private, gated community of Ventur ...
From $283 per night (USD)VRBO
From $215 per night (USD)VRBO
Coastal Oasis, Canal front
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
COASTAL OASIS is just for you. This three-bedroom two-bath canal-front home offers a comfortable base for your Keys adve ...
From $215 per night (USD)VRBO
From $215 per night (USD)VRBO
Cudjoe Bay Overlook
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This really nice custom Keys home is located in a very quiet area with good boating access to both the Atlantic with its ...
From $215 per night (USD)VRBO
From $401 per night (USD)VRBO
LICENSE TO CHILL ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CUDJOE JEWEL WITH AMENITIES GALORE… Incredible panoramic views will dazzle and beguile you from the moment you lay eyes ...
From $401 per night (USD)VRBO
From $387 per night (USD)VRBO
COCONUT TELEGRAPH ~ Waterfront 2 BR\/2Ba in Cudjoe Key w\/ Dockage & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CUDJOE CUTIE WITH AMENITIES GALORE… Sweeping views of the dazzling turquoise waters of the Florida Keys will ignite your ...
From $387 per night (USD)VRBO
From $283 per night (USD)VRBO
Sunset Views, oceanfront
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the sunsets on Sarcarma Bay from this rustic home in a tropical setting with an open waterfront and canal access. ...
From $283 per night (USD)VRBO
From $300 per night (USD)VRBO
Shore Thing at Venture Out With 50’ Private Dock, Bring Your Boat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NEW LISTING JULY 2023!!! Welcome to Shore Thing at Venture Out! This remarkable home features unparalleled Atlantic V ...
From $300 per night (USD)VRBO
From $379 per night (USD)VRBO
Tropical paradise on open water 35 ft seawall in beautiful Venture Out Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ocean Front 35’ Seawall – Spectacular views from this 2 Bedroom 2 Bathroom ocean front stilt home! This home features a ...
From $379 per night (USD)VRBO
From $599 per night (USD)VRBO
Oceanfront Venture Out Home on Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to paradise in Slow M'Ocean at this stunning ocean front home located in the private, gated community of Venture ...
From $599 per night (USD)VRBO