Summerland Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Summerland Key, Florida on RentalSaver.com!

Summerland Key Rentals

From $174 per night (USD)
VRBO
RV Lot 498 in Venture Out at Cudjoe Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
**THIS IS FOR AN RV LOT ONLY - THIS RENTAL DOES NOT INCLUDE AN RV - JUST THE LOT SITE** Welcome to your own private oas ...
From $174 per night (USD)
VRBO
From $467 per night (USD)
Expedia
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 $467 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Wahoo Waterway: Charming 3BR Canal Front Home in Cudjoe Key with Dockage & Pet-Friendly Amenities!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $206 per night (USD)
VRBO
Click For Pricing
Expedia
Latitude Adjustment in Cudjoe Key #264
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 ...
Click For Pricing
Expedia
From $237 per night (USD)
VRBO
Oceanview at 372, Venture Out Cudjoe Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Oceanview at 372. Escape to a serene oasis with our charming Oceanview rental in the picturesque Florida Keys ...
From $237 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Bimini Breeze - VO 313
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Bimini Breeze - VO 313 Walk to Pool and Marina! Centrally Located Charming 2Bd/1Ba This home is located on a quiet circl ...
From $387 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Tarpon Alley - Venture Out 509
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tarpon Alley - VO509 Canal Front35' Dockage Casually elegant, beautifully decorated, and fully stocked for your conveni ...
From $358 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Casa Kiwi #472 - Ocean Views on Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Kiwi, your perfect getaway in the heart of the beautiful Florida Keys. Nestled on a serene interior lar ...
From $380 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Island Home in Paradise #624 - OCEANFRONT Community!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Island Home in Paradise, your ideal vacation rental nestled in the heart of the Florida Keys – a wonderful re ...
From $270 per night (USD)
VRBO
From $318 per night (USD)
VRBO
2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Gecko House! This canal-front 2 bedroom, 2 bath house is located in a great boating area with easy access to ...
From $318 per night (USD)
VRBO
From $788 per night (USD)
VRBO
The Roost in Summerland Cove Isles
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The Roost in Summerland Cove Isles affectionately know as 'The Castle' is truly a gem nestled in a highly desirable neig ...
From $788 per night (USD)
VRBO
From $272 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 $272 per night (USD)
VRBO
From $683 per night (USD)
VRBO
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 ...
From $683 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Aqua Vista
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bright, colorful and tropical this freshly remodeled home is located within easy walking distance to convenience store a ...
From $237 per night (USD)
Expedia
From $911 per night (USD)
VRBO
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! This beau ...
From $911 per night (USD)
VRBO
From $973 per night (USD)
Expedia
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Waterfront Home with Stunning Ocean Views! Welcome to this amazing Florida Keys getaway! This beautiful 2-bed ...
From $973 per night (USD)
Expedia
From $2130 per night (USD)
VRBO
Luxurious 6 Bedroom 8 Bath Open water pool home on Ramrod Key with great boating
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Welcome to your tropical paradise on Ramrod Key! This stunning 6,888 square foot home showcases exceptional quality in b ...
From $2130 per night (USD)
VRBO
From $264 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 $264 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views! Escape to paradise in this luxurious 3 bedroom, ...
From $314 per night (USD)
VRBO
From $144 per night (USD)
Expedia
219 Oceanfront RV Lot 59' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your dream RV Getaway on a stunning Oceanfront lot! Perfect for large RV's, boats with this huge 59' concrete ...
From $144 per night (USD)
Expedia
From $403 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 $403 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Paradise Point Getaway in Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
🌴 Your Tropical Paradise Awaits! 🌊 Step onto the large covered porch and soak in the breathtaking water views that st ...
From $301 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Cozy Retreat w/ Great Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Comfortable one-bedroom, one-bathroom getaway in the gated Venture Out community, just minutes from Bahia Honda State Pa ...
From $271 per night (USD)
VRBO
From $395 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! This beautiful 2-bedroom, 2- ...
From $395 per night (USD)
Expedia
From $423 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 $423 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Summerland Sanctuary: 3BR Canal Front Retreat with Private Pool, Dockage & Premier Boating/Fishing
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $302 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Tropical Island Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Get ready to relax in this delightful 2-bedroom resort in Cudjoe Key. With 2 queen beds, a cozy living room with an extr ...
From $329 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Latitude Adjustment #598, Canal front-Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Need a “LATITUDE ADJUSTMENT”? This spotless 2 BR, 2 BA stilt home on a 60' wide canal in Venture Out at MM23, on Cudjoe ...
From $296 per night (USD)
VRBO
From $362 per night (USD)
VRBO
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 $362 per night (USD)
VRBO
$Heavenly Hideaway 284\nCharming 2-bedroom house in serene Cudjoe Key w/ WiFi, AC$
From $380 per night (USD)
VRBO
Heavenly Hideaway 284\nCharming 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 $380 per night (USD)
VRBO
$Salty Breezes 285\nCharming 2-bedroom house in pleasant Cudjoe Key with WiFi, AC$
From $374 per night (USD)
VRBO
Salty Breezes 285\nCharming 2-bedroom house in pleasant Cudjoe Key with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SALTY BREEZES: is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expan ...
From $374 per night (USD)
VRBO
From $281 per night (USD)
VRBO
3 bedroom, 2 bath, canal home with hot tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the beauty of Cudjoe Key from this marvelous 3-bedroom house. This delightful property features 1 queen bed, 2 ...
From $281 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Sunny Gens - Venture Out #606
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SUNNY GENS Turn Key 2Bd/2Ba with Canal Views! 35' Dockage Quick Ocean Access! Beautiful turn key stilt 2Bd/2Ba home in ...
From $377 per night (USD)
VRBO
From $173 per night (USD)
VRBO
RV Lot 502 Venture Out, Located on a boating canal
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience the tranquility of this landscaped canal front RV lot nestled within Venture Out. This spacious 35'x69'x17'x3 ...
From $173 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Canal Front Home in Gated Community. Salt Life #182
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Live the Salt Life #182 here at Venture Out. in a gated community on Cudjoe Key located at Mile Marker 23 in the Florida ...
From $278 per night (USD)
VRBO
From $184 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 $184 per night (USD)
VRBO
From $261 per night (USD)
VRBO
SEA COVE ~ Canal Front 2 BR/2 Ba Home in Cudjoe Key w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
LOWER KEYS WATER WORLD… Come on down to some of the most beautiful natural vistas and the serene environment of Cudjoe K ...
From $261 per night (USD)
VRBO
From $237 per night (USD)
Expedia
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
CUDJOE NEST WITH ENDLESS AMENITIES … This cozy cutie is nestled in the amazing Venture Out Resort! Your clean and comfy ...
From $237 per night (USD)
Expedia
From $365 per night (USD)
VRBO
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 seren ...
From $365 per night (USD)
VRBO
From $436 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 L ...
From $436 per night (USD)
VRBO
From $173 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 $173 per night (USD)
VRBO
$Sea Glass House of Summerland Key!\nPool, 70 feet of Seawall, deep water canal!$
From $412 per night (USD)
Expedia
Sea Glass House of Summerland Key!\nPool, 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 $412 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Mahi House #440 - 35' seawall
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Mahi House #440 Escape to paradise at Mahi House #440, your perfect getaway nestled along a quiet boating ...
From $425 per night (USD)
VRBO
From $368 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 $368 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Cozy Canal-Front Home in Cudjoe Key — Dock, Hot-Tub & Golf Cart Included!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect island getaway in Cudjoe Key! This beautiful 3-bedroom, 2-bathroom canal-front home offers every ...
From $242 per night (USD)
VRBO
From $312 per night (USD)
Expedia
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 $312 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Ocean Breeze at Venture Out 537
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Lovely Vacation Home with Large Enclosed Porch! This beautiful, newly remodeled home, is an island oasis and is located ...
From $261 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Fishermans Paradise@The Pointe on Summerland Key 2Bed/2Bath, Pool, 120' of Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Fishermans Paradise @ The Pointe on Summerland Key in the Fabulous Florida Keys. Fishermans Paradise @ The Po ...
From $400 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Rv empty lot campground in Cudjoe Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover the beauty of CudJoe Key from this Rv Lot campground. Nestled in a serene setting, this welcoming retreat offer ...
From $168 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Pelican Perch – 3BR Canal Front Home with Dockage, Pet-Friendly, Quick Access to Atlantic & Gulf!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $239 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Keys getaway - Relax with the whole family at this peaceful place to stay.
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This marvelous house in Cudjoe Key offers a cozy one bedroom with a queen bed, one and half bathrooms, and an additiona ...
From $368 per night (USD)
VRBO
Click For Pricing
Expedia
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your Little Piece of Paradise #233 here at the gated community of Venture Out! This cozy, canal front, 1-bed ...
Click For Pricing
Expedia
From $326 per night (USD)
VRBO
Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Drive In, Fly In. Boat Out. Live Elevated. Welcome to a truly rare gem nestled between Marathon and Key West—a sol ...
From $326 per night (USD)
VRBO
From $155 per night (USD)
VRBO
RV Lot 527 Venture Out, 35x69 35' seawall and Ocean Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
**Please note that this is for an RV Lot only - You will need to bring your own RV** 35' x 69' Waterfront RV Lot with E ...
From $155 per night (USD)
VRBO
From $454 per night (USD)
VRBO
The Diving Dolphin #268 - Ocean Views, Kayaks!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Diving Dolphin #268 - Waterfront Getaway | 2BR/2BA | Ocean Views, 2 Kayaks, 2 Bicycles, 2 Paddleboards, 35' Seawall ...
From $454 per night (USD)
VRBO
From $497 per night (USD)
Expedia
Tides & Tranquility - Venture Out Unit 053
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in Cudjoe Key. This charming ocean front home has breathtaking views of the Atlantic Ocean and spect ...
From $497 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Stunning Open Water RV Lot with 38' Seawall and Great Amenities in Gated Community
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your perfect Florida Keys getaway. This stunning RV lot is located directly on the open water, offering unint ...
From $204 per night (USD)
VRBO
From $667 per night (USD)
Expedia
Oceanfront w/stunning open water views and a 60-foot dock! 30 mins to Key West!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Oceanfront with stunning open water views and deep water access! Oceanview Serenity offers stunning Atlantic views, a ma ...
From $667 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Oversized RV Lot with 41'+12' Seawall, Deep Water Access, and Stunning Open Water Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your slice of paradise in the Florida Keys. This exceptional open-water RV lot is located in the desirable ga ...
From $205 per night (USD)
VRBO
From $339 per night (USD)
Expedia
35' dock completely remodeled Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Dock your boat behind the house and enjoy open water view. Located in Cudjoe Key, this newly renovated house offers 2 be ...
From $339 per night (USD)
Expedia
From $100 per night (USD)
VRBO
RV Lot 301 Venture Out, Pull-through Lot near the Ocean and Pool - Golf cart friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
**This is for an RV Lot ONLY*** Welcome to Lot 301, a beautifully maintained 35x69 pull-through RV lot featuring great ...
From $100 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Sept. Special, Waterfront, Dock,Kayak, Paddleboard, golf cart, bicycles
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Get ready to relax in this spacious and serene 2-bedroom waterfront resort villa in Cudjoe Key. Our exquisitely design ...
From $320 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Waterfront RV Lot Just 2 Spots from Open Water with 35' Seawall—Fish, Boat & Relax in Paradise!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your slice of paradise! This exceptional RV lot is perfectly situated near the end of a peaceful canal—just t ...
From $178 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Cudjoe Key, this house is a dream. With 2 bedrooms featuring 2 full beds, 2 bathrooms with showers and hair d ...
From $397 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Sea Cow Key Cottage - Venture Out Unit 585
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sea Cow Key Cottage - VO585 Open Water Views! 2Bd/2Ba 26' + 9' Dockage on Wide Lagoon! OPEN WATER and DEEP WATER ACCES ...
From $421 per night (USD)
VRBO
From $463 per night (USD)
Expedia
Sunset Serenity – 3BR Open Water Oasis On Summerland Key Boat Dockage, Stunning Views & Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Sunset Serenity – Your Open Water Escape in the Lower Keys! Unwind in paradise at Sunset Serenity, a stunnin ...
From $463 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Waterfront Property, Boat Dock, Heated Pool Gated Community, Waterfront Home, Heated Pool, Boat Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coastal 2-bed, 2 bath waterfront home located on a wide canal that is perfect for the avid boaters! Private 35-ft dock f ...
From $442 per night (USD)
VRBO
From $611 per night (USD)
Expedia
Galleon Getaway #533- Oceanfront Community
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Galleon Getaway #533, a charming 2-bedroom, 1-bath home located in a gated oceanfront community. The primary ...
From $611 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Serenity Now Seaside Escape - Brand New Build!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your exquisite Florida Keys getaway in the prestigious gated community of Venture Out on Cudjoe Key, where th ...
From $492 per night (USD)
VRBO
From $138 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 $138 per night (USD)
VRBO
From $284 per night (USD)
VRBO
Breezy Point - Venture Out Unit 199
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Breezy Point - VO199 Across from Open Water! This manufactured home is located on an oversized corner across the street ...
From $284 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3BR Stilted Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key Lime Hideaway #397 - 3BR/2BA Stilted Home w/ Ocean Views Welcome to Key Lime Hideaway — your sun-soaked home base i ...
From $505 per night (USD)
Expedia
From $366 per night (USD)
VRBO
**DOLPHIN DAYDREAMS @ VENTURE OUT** New Home in Resort Community + LAST KEY SERV
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! DOLPHIN DAYDR ...
From $366 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Looking for the ultimate Keys Vacation here it is 4 bedroom 3.5 Bath Pool Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
If you are looking for the ultimate Keys vacation, your search is over!! This private 4 bedroom 3.5 bath luxury estate h ...
From $758 per night (USD)
Expedia
From $608 per night (USD)
VRBO
Beautiful 3 bedroom 2 bath open water pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Gorgeous open water 3 bedroom 2 bath pool home on Summerland Key! This completely remodeled home features an open floor ...
From $608 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Gorgeous 4 bedroom 3 bath open water pool home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to Corcovado, this luxury estate sits on one of the finest properties in the Lower Florida Keys. Incredible deep ...
From $736 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Beautiful 3 bedroom 3 bath open water pool home on Summerland Key
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 $567 per night (USD)
VRBO
From $291 per night (USD)
Expedia
3 bedroom 2 bath home located on Summerland Key airstrip with great boating.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious 3-Bedroom, 2-Bath Home on Summerland Key Airstrip Discover the ultimate getaway in this inviting 3-bedroom, 2-b ...
From $291 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Gorgeous 4 bedroom 2.5 bath pool home on great boating canal
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Beautiful and cozy 4 bedroom, pool home located on Cudjoe key with excellent boating access to the Atlantic or the Gulf. ...
From $333 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Tropical 3BR on Canal – Dock for 30' Boat, Outdoor Shower, Bikes, Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casa Mojito – Your Slice of Paradise in the Lower Keys. Escape to this beautifully landscaped 3-bedroom, 2-bath canalfro ...
From $265 per night (USD)
Expedia
From $355 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 $355 per night (USD)
VRBO
From $689 per night (USD)
Expedia
Summerland Serenity Brand New Waterfront Luxury<br> B
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Summerland Serenity Brand New Waterfront Luxury (Professional Photos Coming Soon)Be the first to experience Summerland ...
From $689 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Group Therapy, your ultimate Florida Keys escape! This updated 3-bedroom, 2-bath waterfront home in Cudjoe Ke ...
From $418 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Oceanfront 2BR/2BA in Cudjoe Key | 50' Seawall, Dock, Open Porch, Stunning Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Mariner's Nook, a charming 2-bedroom, 2-bath getaway perched at the corner of a canal and open water, offerin ...
From $426 per night (USD)
Expedia
From $195 per night (USD)
VRBO
Corner RV Lot with Lagoon Views, Palm Trees, and Steps to Pool & Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover Your Perfect RV Getaway in the Florida Keys Set on a spacious corner lot framed by mature palm trees and coasta ...
From $195 per night (USD)
VRBO
From $435 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 $435 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Gorgeous 3 Bedroom 2 Bath Open Water Pool Home on Summerland Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gorgeous open water 3 bedroom 2 bath pool home on Summerland Key! This completely remodeled home features an open floor ...
From $559 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Beautiful 3 Bedroom 3 Bath Open Water Pool Home With Excellent Boating
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 $610 per night (USD)
Expedia
From $791 per night (USD)
VRBO
Gorgeous 4 Bedroom 3 Bath Open Water Pool Home with great boating
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Corcovado, this luxury estate sits on one of the finest properties in the Lower Florida Keys. Incredible deep ...
From $791 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Spectacular 4 bedroom 2 bath pool home with great boating
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautiful and cozy 4 bedroom, pool home located on Cudjoe key with excellent boating access to the Atlantic or the Gulf. ...
From $356 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Beautiful 3 Bedroom Canal Front Home Located On A Private Airstrip
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Spacious 3-Bedroom, 2-Bath Home on Summerland Key Airstrip Discover the ultimate getaway in this inviting 3-bedroom, 2-b ...
From $303 per night (USD)
VRBO
From $1053 per night (USD)
Expedia
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
🏡 Amenities: Dock, Guest Cottage, Pool, Spa, Outdoor Kitchen, Firepit 🌊 Kayaks, and Paddle Boards 📍 30 Minutes to K ...
From $1053 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to the Florida Keys and enjoy this inviting 2-bedroom, 2-bath waterfront home in Venture Out on Cudjoe Key—just 1 ...
From $424 per night (USD)
VRBO

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Results: 293 Rentals