Summerland Key Rentals
From $495 per night (USD)VRBO
Ocean Vue in Cudjoe Key #469
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Upscale Ocean Vue Retreat with breathtaking views from Sunrise to Sunset! This waterfront gem offers amazing views and i ...
From $495 per night (USD)VRBO
From $274 per night (USD)Expedia
FLORIDA KEYS PARADISE! DEEP WATER CANAL WITH FAST OCEAN ACCESS.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Carribean Paradise is a beautiful 3 bedroom 3 bathroom house in a quiet, beautiful neighborhood. Large corner lot with ...
From $274 per night (USD)Expedia
From $467 per night (USD)VRBO
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom in Venture Out Community!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
CUDJOE NEST WITH ENDLESS AMENITIES … This cozy manufacture home is nestled in the amazing Venture Out Resort, a gated r ...
From $467 per night (USD)VRBO
From $487 per night (USD)Expedia
Sea Glass House of Summerland Key! Pool, 70 feet of Seawall, deep water canal!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Get ready to relax in this beautiful 3-bedroom house in Summerland Key Cove. This property features three large bedrooms ...
From $487 per night (USD)Expedia
From $601 per night (USD)VRBO
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront 2BR Retreat in Venture Out with 35' Dock, Optional Golf Cart, Heated Pool & Quick Ocean Access Welcome to Mah ...
From $601 per night (USD)VRBO
From $354 per night (USD)Expedia
ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DREAM COASTAL RETREAT… If dazzling open waters and deep draft boating and dockage is what you crave, look no further. We ...
From $354 per night (USD)Expedia
From $481 per night (USD)VRBO
Canal front with open water views in Venture Out - Lot 529
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront Getaway in Venture Out Welcome to your perfect getaway! This beautifully updated vacation home offers comfor ...
From $481 per night (USD)VRBO
From $428 per night (USD)Expedia
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Saltwater Serenity #392, your perfect getaway in the heart of the beautiful Florida Keys. Nestled on a serene ...
From $428 per night (USD)Expedia
From $321 per night (USD)VRBO
Big Blue #230, Canal front - Venture Out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to BIG BLUE #230 in the Gorgeous Florida Keys! Introducing this beautiful vacation home located in the serene Lo ...
From $321 per night (USD)VRBO
From $228 per night (USD)VRBO
RV Lot 377 Venture Out, Waterfront Retreat, Accommodates large/oversized RVs
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This RV lot is a prime waterfront retreat, featuring a lushly landscaped setting that provides both privacy and natural ...
From $228 per night (USD)VRBO
From $321 per night (USD)VRBO
Latitude Adjustment #598, Canal front-Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Need a “LATITUDE ADJUSTMENT”? Unit #598 is a spotless 2 BR, 2 BA stilt home on a 60' wide canal in Venture Out at MM23, ...
From $321 per night (USD)VRBO
From $621 per night (USD)Expedia
Sailfish Haven #390 - Ocean Views, 35' seawall
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Florida Keys Waterfront Retreat with Stunning Ocean Views Welcome to your perfect getaway at Sailfish Haven #390! This b ...
From $621 per night (USD)Expedia
From $228 per night (USD)VRBO
RV Lot 497-35' Canal Front in Venture Out at Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
RV Lot 497 - Available for Long Term or Short Term RV LOT Rental. **This is for an RV Lot ONLY*** Welcome to RV Lot 4 ...
From $228 per night (USD)VRBO
From $933 per night (USD)Expedia
Post Card Point #319 - Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing Waterfront Getaway Overlooking the Marina with Stunning Ocean Views! Welcome to your perfect getaway at Post Car ...
From $933 per night (USD)Expedia
From $314 per night (USD)VRBO
3/2 on the Water in Paradise Monthly Rental 28 Day min.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wonderful, open concept, 3/2 stilt, canal front home in Summerland Key. On the beautiful, blue/green flow through canal ...
From $314 per night (USD)VRBO
From $430 per night (USD)Expedia
Reel Island Retreat #273 at Venture Out in the Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Take that vacation you have been dreaming of in the Florida Keys! Reel Island Retreat #273 is waiting for you! Perfect f ...
From $430 per night (USD)Expedia
From $388 per night (USD)VRBO
Summer Breeze on Summerland Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax on the large porch overlooking a beautiful,flow through,crystal clear,deep water canal with excellent boating acc ...
From $388 per night (USD)VRBO
From $682 per night (USD)Expedia
Spanish Queen @Venture Out, Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnish ...
From $682 per night (USD)Expedia
From $492 per night (USD)VRBO
Waterfront Venture Out Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Mandatory $125 Fee paid to Venture Out Community upon arrival. Waterfront home with concrete seawall for boat dockage. ...
From $492 per night (USD)VRBO
From $208 per night (USD)VRBO
RV Lot Venture Out, 35x69' Accommodates Large/Oversized RVs
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Welcome to this remarkable and generously spacious RV Lot nestled within the beautiful community of Venture Out on Cudjo ...
From $208 per night (USD)VRBO
From $351 per night (USD)VRBO
Venture Out Million Dollar Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront 2BR , King or 2 Twins . Extra guest has a queen sofa sleeper, featuring bright coastal décor and wide open. ...
From $351 per night (USD)VRBO
From $286 per night (USD)VRBO
Water Lovers Paradise
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This newly renovated vacation home on a canal in Cudjoe Key is a stunning retreat that offers the perfect blend of comf ...
From $286 per night (USD)VRBO
From $368 per night (USD)VRBO
Pelican's Roost, Waterfront comfort at Venture Out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
About this space Pelicans Roost is a waterfront home on the Atlantic side of Cudjoe Key with a 17’ dock. Only 20 miles f ...
From $368 per night (USD)VRBO
From $787 per night (USD)VRBO
Paradise place located in a gated resort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island living. Waterfront home ground level , with boat dock/ seawall in your back yard. located Between the Atlantic ...
From $787 per night (USD)VRBO
From $269 per night (USD)VRBO
Cozy Venture Out Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
MANDATORY $125 FEE NOT INCLUDED, PAID TO VENTURE OUT COMMUNITY UPON ARRIVAL. One bedroom home with all that you need. ...
From $269 per night (USD)VRBO
From $240 per night (USD)VRBO
RV Lot 442 Venture Out, Canal Front, 35ftx69ft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to RV Lot 442 in the exclusive gated community of Venture Out, located in stunning Cudjoe Key, Florida! This spa ...
From $240 per night (USD)VRBO
From $214 per night (USD)VRBO
RV Lot 40 Venture Out, Lot dimentions - 35'x69'
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your ideal RV lot in the vibrant Venture Out community on Cudjoe Key! This dry lot, measuring 35' x 69', offe ...
From $214 per night (USD)VRBO
From $228 per night (USD)VRBO
Canal Front RV LOT 451 Venture Out (40x23x70x31x35)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your dream canal front RV Lot with peekaboo ocean views. Situated on a quiet cul de sac, this picturesque lot ...
From $228 per night (USD)VRBO
From $511 per night (USD)VRBO
Oceanfront Dream Home - VO048
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Oceanfront Dream Home - VO048 2Bd/2Ba OCEANFRONT 45' SEAWALL! This BEAUTIFUL 2Bd/2Ba OCEANFRONT with endless ocean vie ...
From $511 per night (USD)VRBO
From $334 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 $334 per night (USD)VRBO
From $401 per night (USD)VRBO
Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated 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 $401 per night (USD)VRBO
From $349 per night (USD)Expedia
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property that won’t disappoint! Full ...
From $349 per night (USD)Expedia
From $331 per night (USD)VRBO
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forwa ...
From $331 per night (USD)VRBO
From $406 per night (USD)Expedia
Ocean/Canal Views 21ft Dock - Venture Out #357
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Ocean/Canal Views 21' Dockage 2Bd/2Ba with Double Porches, Large Landscaped Yard! Island Breeze is a fabulous ...
From $406 per night (USD)Expedia
From $309 per night (USD)VRBO
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House ...
From $309 per night (USD)VRBO
From $263 per night (USD)Expedia
Sunshine 23 | Dog-friendly canalfront home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Dog-friendly canalfront boating home on Cudjoe Key The Space: All the comforts of home, with none of the c ...
From $263 per night (USD)Expedia
From $441 per night (USD)VRBO
**CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! From the mome ...
From $441 per night (USD)VRBO
From $404 per night (USD)Expedia
Peaceful ocean front cottage.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sun ...
From $404 per night (USD)Expedia
From $705 per night (USD)VRBO
Cudjoe Key Home with a View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the ame ...
From $705 per night (USD)VRBO
From $457 per night (USD)Expedia
Atlantic Ocean Views - Venture Out 579
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Atlantic Ocean Views - Venture Out 579 Lovely Stilt 2Bd/2Ba with 35' Dockage This beautiful sparkling clean 2Bd/2Ba stil ...
From $457 per night (USD)Expedia
From $385 per night (USD)VRBO
Relaxing Waterfront Escape Near Key West - Venture Out Unit 410
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO410 Relaxing Waterfront Escape Near Key West – 35' Dock, Kayaks and bikes included. Access to beautiful pool and hot t ...
From $385 per night (USD)VRBO
From $434 per night (USD)Expedia
Waterfront with Boat Dock, Heated Pool, Amenities #573, Waterfront Home, Heated Pool, Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Coastal 2-bed, 2 bath water-front home located on a wide canal that is perfect for the avid boaters! Private 35-ft dock ...
From $434 per night (USD)Expedia
From $611 per night (USD)VRBO
Serenity Now - Canal Views & Resort Fun!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Serenity Now, your canal-side escape in the gated Venture Out community on Cudjoe Key. This beautiful two-bed ...
From $611 per night (USD)VRBO
From $474 per night (USD)Expedia
Cudjoe Key Sportsman's Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Cudjoe Key from this 3-bedroom, fully furnished, over 1800 sq ft house. This gorgeous property fe ...
From $474 per night (USD)Expedia
From $450 per night (USD)VRBO
Fin's Hideaway - Venture Out #259
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VO259 FINS Hideaway Canal Front Home 35' Dockage Beautiful bay views at this canal front home located only 120' from the ...
From $450 per night (USD)VRBO
From $348 per night (USD)Expedia
Cozy, Perfect Conch Cottage! - VO315
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy, Perfect Conch Cottage! VO315 Welcome to our Conch Cottage, located in the beautiful Florida Keys! Everything you n ...
From $348 per night (USD)Expedia
From $469 per night (USD)VRBO
Heavenly Hideaway 284 Charming 2-bedroom house in serene Cudjoe Key w/ WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Heavenly Hideaway is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the ex ...
From $469 per night (USD)VRBO
From $194 per night (USD)VRBO
RV Lot in Oceanfront Community | Concrete Pad, Lush Landscaping, Walk to Pool & On Site Store
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Discover the ideal RV getaway on this spacious 60x20x62x40 lot in a premier oceanfront community in the Florida Keys. Wi ...
From $194 per night (USD)VRBO
From $601 per night (USD)VRBO
Canal-view 2BR/2BA home with pool, hot tub, and dock access.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal-Front 2BR Retreat in Venture Out with Boat Dock, Heated Pool & Pet-Friendly Florida Keys Living Welcome to Keys Ti ...
From $601 per night (USD)VRBO
From $287 per night (USD)Expedia
Relaxing and Inviting home in gated community with 35' Seawall Private Dock
- 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 $287 per night (USD)Expedia
From $350 per night (USD)VRBO
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy ...
From $350 per night (USD)VRBO
From $128 per night (USD)Expedia
RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
RV RESORT SPOT. BIG Rig Friendly discount per month when booking 1ST to the 1ST of the month RV RESORT SITE ...
From $128 per night (USD)Expedia
From $296 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 $296 per night (USD)VRBO
From $287 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 $287 per night (USD)VRBO
From $384 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 $384 per night (USD)VRBO
From $382 per night (USD)VRBO
Spectacular Sunsets, 3 bed, 2 bath with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape completely in this open and airy 3 bedroom 2 bath oceanfront pool home. Situated on the northern shore of Sarcarm ...
From $382 per night (USD)VRBO