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 $324 per night (USD)
VRBO
Bluegill pool, larger boat allowed
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 39' boat. Bea ...
From $324 per night (USD)
VRBO
From $289 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 $289 per night (USD)
VRBO
From $479 per night (USD)
VRBO
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 $479 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Coconut Cottage #653 - Oceanfront Community
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Coconut Cottage, your charming oasis nestled within the exclusive gated community of Venture Out in Cudjoe Ke ...
From $291 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Beautifully Renovated with Stunning Sunset Views and Dockage!
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 $409 per night (USD)
VRBO
From $242 per night (USD)
Expedia
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 $242 per night (USD)
Expedia
From $329 per night (USD)
VRBO
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 $329 per night (USD)
VRBO
From $302 per night (USD)
Expedia
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 $302 per night (USD)
Expedia
From $199 per night (USD)
VRBO
RV Lot 288 Venture Out, Canal Front ,Lot Dimensions:35x69' 35' Dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your own slice of paradise in the Florida Keys! This exceptional 69' x 35' canal front RV lot offers the perf ...
From $199 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Empty RV Lot with Amazing Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Captivating Oceanfront Getaway with 35' Durable Seawall! This property is equipped with a robust seawall featuring dock ...
From $159 per night (USD)
Expedia
From $250 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 $250 per night (USD)
VRBO
From $126 per night (USD)
VRBO
RV Lot 69Venture Out ,Lot Dimensions:35x69'
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your slice of paradise on this 35ft x 69ft RV Lot in the breathtaking Florida Keys! Nestled in the vibrant co ...
From $126 per night (USD)
VRBO
From $321 per night (USD)
VRBO
The Lookout #659 Venture Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Lookout #659 at Venture Out on Cudjoe Key! Experience your perfect getaway at our stunning high-rise vac ...
From $321 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Paradise Escape! - VO466 35' Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO466 Paradise Escape! Perfect Location 35' Dockage! It's a wonderful time to enjoy Paradise! Enjoy endless expansive w ...
From $352 per night (USD)
Expedia
$2bed\/2bath Summerland Key Canal front perfection with pool$
From $482 per night (USD)
VRBO
2bed\/2bath Summerland Key Canal front perfection with pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your ultimate Florida Keys escape! Nestled in the heart of Summerland Key Airport, this contemporary 2-bedroo ...
From $482 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Cudjoe Luxury Pool 3BR 70ft Dock Home- CUJ#22
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom, 70ft Dock Tropical Cudjoe Key Home is located twenty miles from famous Key West. This fantastic waterfront 3B ...
From $339 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Seabreeze Escape WF RV Lot 489
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Seabreeze Escape WF RV Lot 489 Open Water Views! 35' Dockage with Tropical Landscaping!! Fish and swim right from your ...
From $260 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the ultimate in waterfront luxury at Caribbean Cabana, where every moment is a postcard-perfect memory waitin ...
From $337 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Don’t be fooled by canal front listings. Lose yourself in the ever changing beauty of the Atlantic Ocean in this charmin ...
From $401 per night (USD)
VRBO
From $173 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 $173 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Pelicans View - Venture Out Lot 318
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Pelicans View - VO318 Island Gem-Walk to POOL & Marina! Gorgeous Open Water Views! This beautifully remodeled midrise ...
From $332 per night (USD)
VRBO
From $297 per night (USD)
VRBO
Latitude Adjustment, Stunning 3-bedroom, 2-bathroom canal-front property
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream vacation home in the heart of Lower Florida Keys! This stunning 3-bedroom, 2-bathroom canal-front ...
From $297 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Casa Morado - Bring your boat
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This 3 bedroom 1 bath home is located on Summerland Key Cove. This ground floor home is handicap accessible. Bring your ...
From $221 per night (USD)
VRBO
From $543 per night (USD)
Expedia
Keys House - Venture Out Lot 220
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
VO220 Keys Home w/ 40' Dockage 2Bd/2Ba This beautiful home on stilts overlooks the open water with amazing views from ...
From $543 per night (USD)
Expedia
From $135 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 $135 per night (USD)
VRBO
From $170 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 $170 per night (USD)
VRBO
From $219 per night (USD)
VRBO
464 Empty RV Lot with 35' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Empty Canalfront RV Location, Location, Location...options abound at this beautifully landscaped waterfront property wi ...
From $219 per night (USD)
VRBO
From $165 per night (USD)
Expedia
432 Empty Canalfront RV Lot with 32' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Empty Canalfront RV Lot #432 Quick boating access from this great waterfront RV Lot just waiting for you to come visit t ...
From $165 per night (USD)
Expedia
From $159 per night (USD)
VRBO
430 Empty RV Lot with 35' Seawall
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Great Empty Waterfront RV Lot just waiting for you to come visit the beautiful Florida Keys. Private 35-foot seawall, ac ...
From $159 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Paradise Palms in Cudjoe Key #635
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This tropical 2-bedroom, 2 full bathroom home has something for everyone! The kitchen boats new stainless-steel applianc ...
From $293 per night (USD)
Expedia
From $160 per night (USD)
VRBO
RV Lot 500 Venture Out, Private tropical landscape
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your tropical paradise RV retreat! This vibrant 35' x 69' RV lot is your ticket to endless fun and relaxation ...
From $160 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Island Comfort at Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Keys Getaway! Escape to paradise with this charming 3-bd, 2-ba canal-front home, perfect for those looking to unwin ...
From $244 per night (USD)
Expedia
$NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool$
From $698 per night (USD)
VRBO
NEW CONSTRUCTION-4-Bedroom- 3.5 Bathroom - Cudjoe Key- Canal Front W\/ Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind at the Artist House on Tarpon Lane on Cudjoe Key! This perfect new construction waterfront home checks all the ...
From $698 per night (USD)
VRBO
From $279 per night (USD)
VRBO
RV Lot 600 Venture Out, Canal Front, 35ftx70ft
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience the serenity of this recently updated RV lot situated within Venture Out. Spanning 35 by 70 , this expansive ...
From $279 per night (USD)
VRBO
From $492 per night (USD)
VRBO
**SWORDFISH SANCTUARY @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! In the same w ...
From $492 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Blue Lobster Lodge - Venture Out 543 - Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your ultimate island getaway on Cudjoe Key! Step into our charming coastal oasis nestled on a spacious corne ...
From $318 per night (USD)
VRBO
From $166 per night (USD)
VRBO
RV Lot 303 Venture Out, Pull-through Lot near the Ocean and Pool - Bring your golf cart!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
RV in the Keys at Venture Out on Cudjoe Key! This 65' pull through RV Lot is ready for you to arrive with your home on w ...
From $166 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Cudjoe Key Coastal Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your ideal vacation getaway in the heart of the Florida Keys! Located in the serene Cudjoe Key, this charming ...
From $207 per night (USD)
VRBO
From $217 per night (USD)
VRBO
Beautiful 2-bedroom canal home with peak-a-boo open water views in Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in our charming Cudjoe Key rental home! This, small dog friendly beautiful property is nestled among ...
From $217 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Beautiful 3 bedroom 2 bath pool home with great boating
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful and cozy 3 bedroom, pool home located on Cudjoe key with excellent boating access to the Atlantic or the Gulf. ...
From $316 per night (USD)
VRBO
From $188 per night (USD)
VRBO
RV Lot 396 Venture Out, Canal Front, 35ftx70ft
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
**THIS IS FOR AN RV LOT ONLY - THIS RENTAL DOES NOT INCLUDE AN RV - JUST THE LOT SITE** Wanna go RV'ing in the Florida ...
From $188 per night (USD)
VRBO
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 $300 per night (USD)
VRBO
Seafarer's Bliss at Venture Out on Cudjoe Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Seafarer's Bliss, your perfect retreat in the beautiful Florida Keys! This charming rental home features two ...
From $300 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Tropical Florida Keys Resort with Boat Dock + pickleball, Pool and more!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
1 bedroom 1 bath with Direct Ocean Access! Close to the Marina & Pool! pickleball.tennis and game room Coastal R ...
From $331 per night (USD)
Expedia
From $497 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 $497 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Wahoo Waterway: Charming 3BR Canal Front Home in Cudjoe Key with Dockage & Pet-Friendly Amenities!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Wahoo Waterway! Experience the perfect blend of comfort and convenience at Wahoo Waterway, a charming 3BR can ...
From $243 per night (USD)
Expedia
From $546 per night (USD)
VRBO
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 ...
From $546 per night (USD)
VRBO
From $228 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 $228 per night (USD)
VRBO
From $109 per night (USD)
VRBO
Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience Cudjoe Key like a local in this charming 1-bedroom apartment. This nice property offers a cozy living room wi ...
From $109 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Bimini Breeze - VO 313
Bedrooms:
1
Bathrooms:
3
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 $322 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Tarpon Alley - Venture Out 509
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tarpon Alley - VO509 Canal Front35' Dockage Casually elegant, beautifully decorated, and fully stocked for your conveni ...
From $380 per night (USD)
VRBO
From $450 per night (USD)
VRBO
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 $450 per night (USD)
VRBO
From $460 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 $460 per night (USD)
VRBO
$2 Bedroom Canal Home in Cudjoe Key, FL w\/ Private Pool & Extra Loft Space$
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $773 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 $773 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Salty Dog Shack #335 - Ocean Views! Kayaks & Bikes included
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cozy Waterfront Escape with Ocean Views Welcome to your home away from home! This delightful 2 bedroom, 1 bath retreat ...
From $358 per night (USD)
VRBO
From $549 per night (USD)
VRBO
**AZURE DAYDREAM @ SUMMERLAND KEY** Waterfront Home + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! AZURE DAYDREA ...
From $549 per night (USD)
VRBO
$3\/2 on the Water in Paradise Monthly Rental 28 Day min.$
From $295 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 $295 per night (USD)
VRBO
From $378 per night (USD)
VRBO
Reel Island Retreat #273 at Venture Out in the Florida Keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Take that vacation you have been dreaming of in the Florida Keys! Reel Island Retreat #273 is waiting for you! Perfect ...
From $378 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Aqua Vista
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bright, colorful and tropical this freshly remodeled home is located within easy walking distance to convenience store a ...
From $242 per night (USD)
Expedia
From $141 per night (USD)
VRBO
RV Lot with 35' Dock & Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Exprience the best the Lower Florida Keys has to offer in this rare find. Our lot boasts a 35' dock equipped with whips, ...
From $141 per night (USD)
VRBO
From $844 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! This beau ...
From $844 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Spacious 3-Bedroom, 2-Bath Canal Front Home on Summerland Key Airstrip
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Discover the ultimate getaway in this inviting 3-bedroom, 2-bath home, perfectly situated on Summerland Key. Ideal for f ...
From $336 per night (USD)
VRBO
From $910 per night (USD)
Expedia
Caribbean Blue #517 Oceanfront Property!
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 $910 per night (USD)
Expedia
From $2029 per night (USD)
VRBO
Luxurious 6 Bedroom 8 Bath Open water pool home on Ramrod Key with great boating
Bedrooms:
7
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 $2029 per night (USD)
VRBO
From $279 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 $279 per night (USD)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $151 per night (USD)
VRBO
RV Lot 611 Venture Out, Beautiful Pull-thru Site 34x51x30x69
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience the Keys Life here at RV Lot 611 inside Venture Out on Cudjoe Key. This spacious pull through Lot measures 3 ...
From $151 per night (USD)
VRBO
From $141 per night (USD)
VRBO
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 $141 per night (USD)
VRBO

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Results: 269 Rentals