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 $274 per night (USD)
VRBO
Beautiful Lagoon view on canal pool home Summerland
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Home has to be rented for 28 days or longer. Home has high vaulted ceiling and 30 feet of sliding glass windows which ...
From $274 per night (USD)
VRBO
From $248 per night (USD)
VRBO
A slice of paradise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Wanna go on vacation but feel Cozy as if your home? We got the place for you! 2 bedroom,1 bathroom with living room,di ...
From $248 per night (USD)
VRBO
From $268 per night (USD)
VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $268 per night (USD)
VRBO
From $631 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 $631 per night (USD)
VRBO
From $426 per night (USD)
VRBO
BIG BLUE waits for you in the sunny Keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our vacation home in the Lower Keys awaits your arrival! We live here during the winter so our home is available spring ...
From $426 per night (USD)
VRBO
$Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights$
From $499 per night (USD)
VRBO
Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' seawal ...
From $499 per night (USD)
VRBO
From $1090 per night (USD)
VRBO
Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set ...
From $1090 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Sirena Key Cottage in Venture Out
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $333 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Kelly's Kabin - Adorable Private Summerland Key Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $358 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Canal house with dock.
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 $290 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Cudjoe Bay Getaway In Paradise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $252 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Casa Del Mar in Venture Out Unit 253
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
VO253 Open Water Views 35' Dockage Sparkling Clean 2Bd/1Ba Vacation Home! THIS IS ONE OF THE NICEST UNITS IN ALL OF VENT ...
From $344 per night (USD)
Expedia
$September Special Rate! Book Now at this canal front pool home\n\n$
From $355 per night (USD)
VRBO
September Special Rate! Book Now at this canal front pool home\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $355 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. ...
From $349 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Seascape Vacation!!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful vacation spot on Cudjoe Key perfect for you and your family. This wonderful one bedroom home filled with color ...
From $276 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Seas The Day in Cudjoe Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A cozy and small mobile home with Marina access and a boat ramp. With almost perfect weather you experience in the Keys ...
From $285 per night (USD)
Expedia
From $254 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 $254 per night (USD)
VRBO
From $370 per night (USD)
Expedia
Springs Venture Out Dolphin House (#386) with beautiful open water views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Home has some of the absolute best views of the Ocean; sitting on your deck watching nature at its best. Our 35ft s ...
From $370 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Minimum Rental is 28 Days to a single family or party (no subleases allowed). Simply Breathtaking VIEWS of the sunset ...
From $256 per night (USD)
VRBO
$Relaxing 2\/2 Get Away in the Lower Keys!$
From $334 per night (USD)
Expedia
Relaxing 2\/2 Get Away in the Lower Keys!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recent ...
From $334 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Views Views! Direct Oceanfront, Beautiful Inside!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless d ...
From $317 per night (USD)
VRBO
$Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise$
From $286 per night (USD)
Expedia
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $286 per night (USD)
Expedia
$Group Therapy | 3 bed, 2 bath home w\/ new pool, quick ocean access$
From $334 per night (USD)
VRBO
Group Therapy | 3 bed, 2 bath home w\/ new pool, quick ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream escape! This beautifully remodeled 3-bedroom, 2-bathroom pool home on Cudjoe Key's oceanside is th ...
From $334 per night (USD)
VRBO
From $1328 per night (USD)
Expedia
One of the very few beach houses with a daily, rental license in the Keys.
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This is a newly remodeled four bedrooms elegant house. The property located in the heart of Summerland Key. It is the ...
From $1328 per night (USD)
Expedia
From $168 per night (USD)
VRBO
EMPTY RV LOT - Sea Esta in Cudjoe Key!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This RV LOT has it all!This is a great spot for those who want to enjoy open water views without having the hassle of ge ...
From $168 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Island Therapy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $316 per night (USD)
Expedia
$NEPTUNES END - 4 Bedrooms \/ 3 Bathrooms Waterfront Retreat- Pool & Sunset Views$
From $507 per night (USD)
VRBO
NEPTUNES END - 4 Bedrooms \/ 3 Bathrooms Waterfront Retreat- Pool & Sunset Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Neptune’s End is the perfect island getaway home. This home sits ocean front and has unobstructed views of Cudjoe Bay ou ...
From $507 per night (USD)
VRBO
From $330 per night (USD)
VRBO
Canal Front (Deep Water) Tropical Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...
From $330 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Relax by Florida Keys Beaches, just a 7-min drive away
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
In beautiful Summerland Key, you'll find our lovely two-bedroom getaway that showcases stunning Florida Keys scenery. Si ...
From $305 per night (USD)
VRBO
From $359 per night (USD)
Expedia
water at your back door
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $359 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Enjoy Caribbean weather in the USA. Openings in April 2025!! Book now!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our home is a bungalow with cathedral ceilings. It is spacious and sparkling clean. Our home is #655 at Venture Out on ...
From $223 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Mariners Cove - The Kraken House
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet C ...
From $586 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
This beautifully furnished, very clean, well-stocked modern house is located in Venture Out, a private residential commu ...
From $362 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Relax at the flying hogfish
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West an ...
From $233 per night (USD)
VRBO
From $752 per night (USD)
VRBO
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come stay with us at VENTURE OUT, a fantastic safe, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $752 per night (USD)
VRBO
From $345 per night (USD)
Expedia
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to The Salty Sailfish, a magnificent canal-front home nestled on Cudjoe Key. With updated furnishings and a comm ...
From $345 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Fishermen’s Paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This is a water lover or a Fisherman’s Paradise. This waterfront home can sleep 6. The house is fully furnished with a ...
From $281 per night (USD)
VRBO
$**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool$
From $500 per night (USD)
Expedia
**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $500 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Tropical Getaway in Paradise.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bedr ...
From $258 per night (USD)
VRBO
From $425 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 $425 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $521 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 $521 per night (USD)
Expedia
From $239 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 $239 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Florida keys Waterfront,Forever Summer
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $410 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Oceanfront Sunsets in the Florida Keys
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FOLSOM'S FOLLY... Summerland Key, Florida Interesting architecture with breezy views of the water. All rooms beautiful ...
From $469 per night (USD)
VRBO
From $227 per night (USD)
VRBO
Cozy and modern island living, Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit #617 Bright, modern, 2bed, 2bath, midrise home. Across from canal and common area. Open floor plan, hardwood, c ...
From $227 per night (USD)
VRBO
From $352 per night (USD)
VRBO
3 night minimum! Spectacular Ocean Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Nite Minimum Stay! Spectacular Ocean Views! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** Newly renovated 2 be ...
From $352 per night (USD)
VRBO
From $489 per night (USD)
Expedia
Ocean Front Modern Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...
From $489 per night (USD)
Expedia
From $318 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 $318 per night (USD)
VRBO
From $402 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 $402 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to eithe ...
From $255 per night (USD)
VRBO
From $390 per night (USD)
Expedia
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Residential Condominium! Is located on a 60' wide canal ...
From $390 per night (USD)
Expedia
$Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key$
From $214 per night (USD)
VRBO
Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stai ...
From $214 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $220 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilt ...
From $347 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Located on a private and quiet open water lot, this charming cottage offers a wonderful view even to those people who do ...
From $315 per night (USD)
VRBO
$Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.$
From $344 per night (USD)
VRBO
Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is your home away from home. Beautiful 3 story home with spacious master bedroom and bathroom located on top floor ...
From $344 per night (USD)
VRBO
$Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security$
From $253 per night (USD)
Expedia
Oceanside Paradise: Kayaks, Free WiFi, A\/C, Grill, Elevated Deck, 24hr Security
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Description: Beautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an ...
From $253 per night (USD)
Expedia
$RELAX IN HEAVENLY PARADISE - CUDJOE KEY GETAWAY\n3 MINUTES TO OPEN WATERS$
From $161 per night (USD)
VRBO
RELAX IN HEAVENLY PARADISE - CUDJOE KEY GETAWAY\n3 MINUTES TO OPEN WATERS
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wow!!! Our new spacious 3 bedroom 2 full bath home on a 60 foot wide deep water canal with a 60 foot dock only 1500 fee ...
From $161 per night (USD)
VRBO
$Captains Quarters - Cudjoe Key - Pool- Waterfront w\/ Boat Dock$
From $484 per night (USD)
Expedia
Captains Quarters - Cudjoe Key - Pool- Waterfront w\/ Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Captain’s Quarters located on the beautiful Cudjoe Bay. This waterfront estate checks all the boxes and is ...
From $484 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Waterfront Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You found it!! Bring your boat! Charming cottage located in Venture Out, resort style community located on Cudjoe Key, ...
From $293 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Canal Front Home, Heated Pool, Fisherman's Dream
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sailfish Escape is a beautiful 3 bedroom, 2 bath 1400 sq ft home on a peaceful canal. Beautiful large fully stocked kitc ...
From $226 per night (USD)
VRBO
From $307 per night (USD)
VRBO
waterfront cottage near key west, sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your d ...
From $307 per night (USD)
VRBO
From $403 per night (USD)
Expedia
Oceanfront Home With Large Private Deck with boat dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy boating, swimming or just the ocean view in the greatest of privacy. Dinner and entertainment in Key West is a sho ...
From $403 per night (USD)
Expedia
$Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry$
From $309 per night (USD)
VRBO
Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Summerland Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $309 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water views. Located on the ...
From $391 per night (USD)
VRBO
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $186 per night (USD)
VRBO
Waterfront beach house with boat ramp
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Waterfront home with private boat ramp. Cozy remodeled 2 bedroom 2 bath (plus bonus room and outdoor shower). Enjoy bik ...
From $186 per night (USD)
VRBO
From $707 per night (USD)
VRBO
NAUTILUS...ocean front cottage retreat ~
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nautilus... ocean front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll nee ...
From $707 per night (USD)
VRBO
From $266 per night (USD)
VRBO
Oceanside, heated pool, near Key West, space for 20-25 ft boat. Book fall 2025!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 bedroom/2 bath home, sleeps 8. Enjoy early morning coffee or evenings gazing at the stars from the cozy balcony. Dow ...
From $266 per night (USD)
VRBO
From $426 per night (USD)
VRBO
LATITUDE ADJUSTMENT
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Need a “LATITUDE ADJUSTMENT”? Our spotless 2 BR, 2 BA stilt home on a 60’ wide canal in VO at MM23, on Cudjoe Key await ...
From $426 per night (USD)
VRBO
$Canalfront house with private pool, WiFi, private washer\/dryer, and central AC$
From $489 per night (USD)
Expedia
Canalfront house with private pool, WiFi, private washer\/dryer, and central AC
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Skyway Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $489 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Canal front home @ Venture Out Resort in the Florida Keys!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** SUPER beautiful canal front home with open wa ...
From $442 per night (USD)
VRBO
From $868 per night (USD)
Expedia
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
As featured on the TV Show; Selling Coastal, Vista de Sirenas translates to ‘Mermaid Views’ is a piece of paradise with ...
From $868 per night (USD)
Expedia
From $447 per night (USD)
VRBO
44ft Seawall at Sportsman's Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
44ft Seawall at Sportsman's Paradise True Island Paradise. Brand New in the rental program, this 2020 Stilted 2Bd/2Ba ...
From $447 per night (USD)
VRBO
From $379 per night (USD)
Expedia
WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy our little piece of paradise! Casa Del Sol is a cozy 820 square foot home that has everything you want for the per ...
From $379 per night (USD)
Expedia
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VRBO
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 ...
Click For Pricing
VRBO
From $291 per night (USD)
Expedia
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Bedrooms:
1
Bathrooms:
2
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 $291 per night (USD)
Expedia
From $423 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 $423 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Anchors Aweigh: Stunning Oceanfront Views, Dockage, Private Pool, Tiki Hut, Spacious & Dog-Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to Anchors Aweigh – Your Oceanfront Escape on Summerland Key! Discover the perfect blend of relaxation and adve ...
From $458 per night (USD)
Expedia
$Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access$
From $214 per night (USD)
VRBO
Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
The Blue Marlin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $214 per night (USD)
VRBO
$**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool$
From $477 per night (USD)
Expedia
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TURTLE COVE V ...
From $477 per night (USD)
Expedia
From $264 per night (USD)
VRBO
ISLAND PARADISE
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We have central air,1 bedroom, 1 bathroom with fully stocked kitchen, washer and dryer, dishwasher, toaster, keurig duo ...
From $264 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Amazing Open Water Views - Venture Out Unit #374
Bedrooms:
2
Bathrooms:
3
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 $475 per night (USD)
Expedia
From $776 per night (USD)
VRBO
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO093 OCEANFRONT GEM! TRUE SOUTHERN EXPOSURE STILT 2BD/2BA 35' SEAWALL Enjoy breathtaking panoramic ocean views from th ...
From $776 per night (USD)
VRBO
From $244 per night (USD)
Expedia
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit # 3 Sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Star Fish Cottage is a one bedroom unit that includes a Queen-sized bed and TV in the bedroom, a full kitchen, bath ...
From $244 per night (USD)
Expedia
$Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi$
From $340 per night (USD)
VRBO
Canal-front home w\/dock, resort-style amenities, patio, & high-speed WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Dock Holiday Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $340 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Panoramic Ocean Front! Venture Out Unit 522
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
VO522 Panoramic Ocean Front! 42' Boat Dockage!Beautiful light and bright vacation rental overlooks the most breathtaking ...
From $385 per night (USD)
Expedia
$REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool, Boat Dock & Sleeps 8!$
From $569 per night (USD)
VRBO
REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool, Boat Dock & Sleeps 8!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience your dream getaway in beautiful Summerland Key within this spacious 4-bedroom retreat. Nestled just a 5-minut ...
From $569 per night (USD)
VRBO
From $309 per night (USD)
Expedia
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Tropical Island Oasis! Tropical Breezes Across from the Marina! A perfect oasis with beautiful views all day, every day. ...
From $309 per night (USD)
Expedia
From $225 per night (USD)
VRBO
LIVING IN BEAUTIFUL PARADISE
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy the view from the large porch overlooking a deep, wide, crystal blue, clear canal with quick boating access to bot ...
From $225 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Nice home on Atlantic side of Cudjoe Key!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restauran ...
From $201 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This oceanside property has 2 beds 2 baths and sleeps 6 with all updated appliances and furniture. There are kayaks and ...
From $342 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Summerland Breeze - Three house retreat, perfect for multiple families
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...
From $890 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous stilt home with beautiful ocean views. This Lobstering paradise is just 1 house down from open water on a deep ...
From $313 per night (USD)
VRBO
From $689 per night (USD)
VRBO
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a ...
From $689 per night (USD)
VRBO
From $572 per night (USD)
VRBO
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Looking to ma ...
From $572 per night (USD)
VRBO
$Views! Waterfront Niles Channel Pool\/dock Industerial Ice Maker$
From $801 per night (USD)
VRBO
Views! Waterfront Niles Channel Pool\/dock Industerial Ice Maker
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Welcome to Paradise at the End of The Road. This home is so secluded you will think you are on your own private island. ...
From $801 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We invite you to come and relax at Torchview Lookout, your own private waterfront retreat! This 3 bedroom / 2 bathroom ...
From $528 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Waterfront home with numerous amenities on popular Cudjoe Key!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Crystal Clear Canal front home with open water view! Home is located in a desirable community called Venture Out. Fully ...
From $266 per night (USD)
Expedia

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Results: 278 Rentals