Summerland Key Rentals
From $500 per night (USD)VRBO
Latitude Adjustment in Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in a serene location in the Florida Keys, this Oceanfront house offers breathtaking open water views that promis ...
From $500 per night (USD)VRBO
From $199 per night (USD)Expedia
Cuddie Cottage: 2BR Waterfront Home in Venture Out Resort, Open Water Views, Shared Pool & Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Cuddie Cottage, your charming haven nestled within the picturesque Venture Out resort on Cudjoe Key. This del ...
From $199 per night (USD)Expedia
From $424 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 $424 per night (USD)VRBO
From $449 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 $449 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 $305 per night (USD)Expedia
Large 5 Bedroom Canal Home in Summerland Key, FL with Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited ...
From $305 per night (USD)Expedia
From $265 per night (USD)VRBO
Lime in the coconut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
You put the "LIME IN THE COCONUT" and add a little fun! Great times to be had in this very nice 3 bedroom 2 bath custom ...
From $265 per night (USD)VRBO
From $269 per night (USD)Expedia
House, relaxing space,waterfront at Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful house located in Cudjoe Key, one of the most beautiful and relaxing keys in the area with a canal and acc ...
From $269 per night (USD)Expedia
From $250 per night (USD)VRBO
Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has e ...
From $250 per night (USD)VRBO
From $200 per night (USD)VRBO
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 ...
From $200 per night (USD)VRBO
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 $325 per night (USD)Expedia
Tropical Tides in Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an Oceanfront getaway in this Beautiful home, boasting stunning panoramic ocean views. Featuring 2 bedrooms and 2 ...
From $325 per night (USD)Expedia
From $465 per night (USD)VRBO
Windswept Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our newly renovated 3 bedroom, 3 bathroom home with stunning open water views! This modern home is perfect fo ...
From $465 per night (USD)VRBO
From $434 per night (USD)Expedia
Tropical Island Getaway - VO196
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO196 2B/2Ba Tropical Island Getaway! Ocean Views with 35' Seawall! Enjoy breathtaking ocean views from this midrise ...
From $434 per night (USD)Expedia
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 $190 per night (USD)VRBO
Deep water Boating ~ Bay Views ~ 3 bed 2 bath + outside shower
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Thank you for checking out the Key Lime Cottage! This deceivingly spacious 3 bedroom 2 bath home is tastefully furnish ...
From $190 per night (USD)VRBO
From $295 per night (USD)Expedia
Stunning Oceanfront Keys Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 1,200-square foot home is a gorgeous ocean front property just minutes from back country and oceanside fishing. Tuc ...
From $295 per night (USD)Expedia
From $395 per night (USD)VRBO
PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location Location Location! Welcome to our very special community Summerland Key. Summerland is one of the best fishi ...
From $395 per night (USD)VRBO
From $235 per night (USD)Expedia
Paradise in the Fabulous Florida Keys - Fishing and Dive capital of the world.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful open water views with gorgeous Sunsets across Cudjoe Bay. Enjoy happy hour overlooking the canal and dock or o ...
From $235 per night (USD)Expedia
From $300 per night (USD)VRBO
Summerland Key House Open Air Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathro ...
From $300 per night (USD)VRBO
From $155 per night (USD)Expedia
Boat Dock \/ Private Airstrip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your Canal Front Oasis on Summerland Key! Dock your boat along the sea wall, offering convenient access to wo ...
From $155 per night (USD)Expedia
From $293 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 $293 per night (USD)VRBO
From $258 per night (USD)Expedia
Waterfront home with boat\/canal access, screened lanai, & renovated interior
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Endless Summerland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $258 per night (USD)Expedia
From $381 per night (USD)VRBO
NEW LISTING - Beautiful Cottage & Amenities in Gated Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture O ...
From $381 per night (USD)VRBO
From $377 per night (USD)Expedia
Sunny Hideaway - Venture Out Unit 276
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunny Hideaway - Venture Out Unit 276 This beautifully decorated home is located on the water and is located within walk ...
From $377 per night (USD)Expedia
From $605 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 $605 per night (USD)VRBO
From $327 per night (USD)Expedia
Bluegill - 3 bedroom 2 bath on canal. POOL COMING SUMMER 2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 28 day minimum rental home has 3 bedroom 2 bath home has great boating access and dockage for up to a 35' boat. Th ...
From $327 per night (USD)Expedia
From $281 per night (USD)VRBO
Coastal Cudjoe Key Home with Excellent Boating
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the tranquil paradise of Latitudes and Attitudes, a charming 3-bedroom, 2-bathroom home nestled in the picture ...
From $281 per night (USD)VRBO
From $415 per night (USD)Expedia
Location Location! Beautiful views from every angle. Summerland Cove rare point
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
If you’re looking for a coastal experience with a modern peaceful clean stay this home is for you. Stay comfortably in S ...
From $415 per night (USD)Expedia
From $248 per night (USD)VRBO
Venture Out 1 bed\/1 bath Cottage on Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconut Cottage, your charming oasis nestled within the exclusive gated community of Venture Out in Cudjoe Ke ...
From $248 per night (USD)VRBO
From $376 per night (USD)Expedia
Beautifully Renovated, Open Water Sunset Views, Dockage, Direct Boating Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Looking for a vacation rental to get away from it all in the Fabulous Florida Keys? Look no further than our beautifully ...
From $376 per night (USD)Expedia
From $150 per night (USD)VRBO
Venture Out RV lot 223
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
RV223 Beautiful RV Lot Open Water Views Expansive 55' Seawall, Amazing Location! OPEN WATER VIEWS with 55' concrete seaw ...
From $150 per night (USD)VRBO
From $195 per night (USD)Expedia
Endless Ocean Views - RV589
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
RV589 Endless Ocean Views! 64' Dockage Slice of Paradise! Panoramic Ocean Views from this fantastic location, perfect f ...
From $195 per night (USD)Expedia
From $143 per night (USD)VRBO
35'x70'WF RV Site on canal for rent for RV owners. Pet friendly gated community.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Located at Venture Out on Cudjoe Key, 20 miles from Key West this gated community offers a heated saltwater pool overloo ...
From $143 per night (USD)VRBO
From $138 per night (USD)Expedia
Empty RV Lot with Amazing Views!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Captivating Oceanfront Getaway with 35' Durable Seawall! This property is equipped with a robust seawall featuring dock ...
From $138 per night (USD)Expedia
From $260 per night (USD)VRBO
Ocean front home with 4 bedrooms, 4.5 baths and dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
You will be treated to gorgeous sunsets over Cudjoe Bay from this custom built 4 bedroom, 4 1/2 bath (master suite has h ...
From $260 per night (USD)VRBO
From $105 per night (USD)VRBO
RV Lot 69Venture Out, Canal Front ,Lot Dimensions:35x69'
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your slice of paradise in the breathtaking Florida Keys! Nestled in the vibrant community of Venture Out, thi ...
From $105 per night (USD)VRBO
From $288 per night (USD)VRBO
The Lookout-2 bed\/2 bath Unit 659 Venture Out stilted Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your tropical paradise getaway in Cudjoe Key, Florida! Nestled within a secure gated community, this charming ...
From $288 per night (USD)VRBO
From $366 per night (USD)Expedia
Paradise Escape! - VO466 35' Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO466 Paradise Escape! Perfect Location 35' Dockage! It's a wonderful time to enjoy Paradise! Enjoy endless expansive w ...
From $366 per night (USD)Expedia
From $450 per night (USD)VRBO
Plane to Sea - Canal Front 2\/2 with Pool & Airplane Hangar
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your dream vacation getaway in the Florida Keys! The stunning 'Plane to Sea' property offers a unique blend o ...
From $450 per night (USD)VRBO