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 $1316 per night (USD)
VRBO
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 $1316 per night (USD)
VRBO
From $263 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 $263 per night (USD)
Expedia
From $164 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 $164 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Anchors Aweigh 10% off Fall 2025!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $341 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Canalfront house with private pool, WiFi, private washer/dryer, and central AC
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Skyway Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $288 per night (USD)
VRBO
From $722 per night (USD)
Expedia
Summerland Breeze - Three house retreat, perfect for multiple families
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...
From $722 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $196 per night (USD)
VRBO
From $765 per night (USD)
Expedia
Summerland Nest - Ocean view with private beach and pool
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. ...
From $765 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Oceanfront house private beach & protected dockage for up to 36' boat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerl ...
From $349 per night (USD)
VRBO
From $698 per night (USD)
Expedia
Mariners Cove - The Kraken House
Bedrooms:
3
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 $698 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Canal Front (Deep Water) Tropical Villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...
From $317 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 $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 $1137 per night (USD)
VRBO
Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set ...
From $1137 per night (USD)
VRBO
From $672 per night (USD)
VRBO
Beach Bliss, Oceanfront with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. T ...
From $672 per night (USD)
VRBO
From $608 per night (USD)
Expedia
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)
Expedia
From $736 per night (USD)
VRBO
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)
VRBO
$PALM COTTAGE \nSummer vacation Lobster and Fishing season!\nsleeps 4$
From $264 per night (USD)
Expedia
PALM COTTAGE \nSummer vacation Lobster and Fishing season!\nsleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $264 per night (USD)
Expedia
From $1075 per night (USD)
VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $1075 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Florida Keys Paradise!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Looking for the ultimate vacation experience? Our vacation home has everything you need to relax and have fun. We are lo ...
From $465 per night (USD)
VRBO
From $294 per night (USD)
VRBO
No Offering a discount from now until July 21!! 3/2 canal front home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Now $6,500 per month until July 21, 2025. $5,500 per month for August 11-December 23, 2025. Discover the ultimate geta ...
From $294 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Casa Morado - Bring your boat
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Imagine a charming retreat situated on a canal and right on the private airstrip in Summerland Key, Florida. This cozy 3 ...
From $221 per night (USD)
Expedia
From $378 per night (USD)
VRBO
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 $378 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
$OCEAN BREEZE HOUSE \nSummer Vacation bring the family. Fishing and Lobster season$
From $418 per night (USD)
VRBO
OCEAN BREEZE HOUSE \nSummer Vacation bring the family. Fishing and Lobster season
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 pe ...
From $418 per night (USD)
VRBO
From $196 per night (USD)
Expedia
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink, microwave oven and toaster oven. The main ...
From $196 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Love Shack | Charming 2 bed/1 bath cottage on Summerland Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
While not directly waterfront, this retreat boasts convenient access to a nearby boat ramp, making it ideal for boating ...
From $153 per night (USD)
VRBO
From $621 per night (USD)
VRBO
Beautiful Oceanfront Villa with Pool and near Key West, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Make some memories at this unique and family-friendly place. Beautiful, custom designed concrete waterfront pool home wi ...
From $621 per night (USD)
VRBO
From $236 per night (USD)
VRBO
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
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 $236 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Summerland Key Oceanfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our longtime winter tenant who has rented our house from November through April for the last 7 years has bought his own ...
From $349 per night (USD)
VRBO
From $689 per night (USD)
VRBO
Views! Waterfront Niles Channel Pool/dock Industerial Ice Maker
Bedrooms:
3
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 $689 per night (USD)
VRBO
From $624 per night (USD)
VRBO
Paradise Views: Oceanfront/Boating
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy one of Florida's most tranquil oceanfront settings. A romantic interlude and tropical adventure where absolutely e ...
From $624 per night (USD)
VRBO
$FLAMINGO COTTAGE - Summer vacation\nLobster and Fishing season- sleeps 4$
From $238 per night (USD)
VRBO
FLAMINGO COTTAGE - Summer vacation\nLobster and Fishing season- sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Flamingo Cottage is a studio unit that includes a Queen-sized bed in the bedroom area, a full kitchen, bathroom with ...
From $238 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Summerland Cottage- Our Little Piece of Paradise with an Old School Key Vibe!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
** Phone Meeting Required before booking approval!! Host Missy Proctor (561) 667-0160 *** Don't forget to check the VR ...
From $235 per night (USD)
VRBO
From $333 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 $333 per night (USD)
VRBO
From $571 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 $571 per night (USD)
VRBO
From $293 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 $293 per night (USD)
VRBO
From $264 per night (USD)
Expedia
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 $264 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. NO PETS. Please review addit ...
From $314 per night (USD)
VRBO
From $429 per night (USD)
Expedia
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 $429 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Pelicans View - Venture Out Lot 318
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Pelicans View - VO318 Island Gem-Walk to POOL & Marina! Gorgeous Open Water Views! This beautifully remodeled midrise ...
From $300 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $269 per night (USD)
VRBO
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 $269 per night (USD)
VRBO
From $294 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 $294 per night (USD)
Expedia
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
$Waterfront RV Lot w 35' dock in \Venture Out\. Utility hookups & beautiful views$
From $111 per night (USD)
VRBO
Waterfront RV Lot w 35' dock in \"Venture Out\". Utility hookups & beautiful views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
35' dock on a canal in Venture Out! This is a RV lot only, there is no house. Simply drive up with your travel trailer/R ...
From $111 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
From $322 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 $322 per night (USD)
Expedia
From $331 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 $331 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 $751 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 $751 per night (USD)
VRBO
From $315 per night (USD)
Expedia
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 $315 per night (USD)
Expedia
From $496 per night (USD)
VRBO
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 $496 per night (USD)
VRBO
From $276 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 $276 per night (USD)
Expedia
From $361 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 $361 per night (USD)
VRBO
From $588 per night (USD)
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 ...
From $588 per night (USD)
Expedia
From $310 per night (USD)
VRBO
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 $310 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Emerald Seas - Florida Keys Ocean Front Paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...
From $444 per night (USD)
Expedia
From $417 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 $417 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Locate ...
From $315 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Canal-front home w/dock, resort-style amenities, patio, & high-speed WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dock Holiday Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $325 per night (USD)
VRBO
Click For Pricing
Expedia
Dog-Friendly, Canal-Front Home w/Free WiFi, Central AC, Private W/D, Boat Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Blue Marlin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $369 per night (USD)
VRBO
**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 $369 per night (USD)
VRBO
From $313 per night (USD)
Expedia
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)
Expedia
From $445 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 $445 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Canal front home @ Venture Out Resort in the Florida Keys!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3 Nite Minimum Stay! **5 day minimum for Lobster Fest, July 22-Aug. 13. ** SUPER beautiful canal front home with open wa ...
From $434 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Nice home on Atlantic side of Cudjoe Key!
Bedrooms:
1
Bathrooms:
2
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 $223 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Sirena Key Cottage in Venture Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $306 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Kelly's Kabin - Adorable Private Summerland Key Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $494 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Cudjoe Bay Getaway In Paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $235 per night (USD)
VRBO
From $268 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 $268 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key
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 $264 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 $264 per night (USD)
Expedia
From $268 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 $268 per night (USD)
VRBO
From $268 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 $268 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
Bedrooms:
2
Bathrooms:
2
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 $264 per night (USD)
VRBO
From $271 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 $271 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Group Therapy | 3 bed, 2 bath home w/ 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 $370 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
Bedrooms:
2
Bathrooms:
2
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 $430 per night (USD)
Expedia
From $392 per night (USD)
VRBO
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
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 $392 per night (USD)
VRBO
From $369 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 $369 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Tropical Getaway in Paradise.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
3 Nite Minimum Stay! ** 5 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bed ...
From $256 per night (USD)
VRBO
From $359 per night (USD)
Expedia
water at your back door
Bedrooms:
2
Bathrooms:
2
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 $219 per night (USD)
VRBO
Enjoy Caribbean weather in the USA. Summer openings!
Bedrooms:
1
Bathrooms:
2
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 $219 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Island Therapy
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $293 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
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 $354 per night (USD)
VRBO
From $462 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 $462 per night (USD)
Expedia
From $221 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 $221 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $224 per night (USD)
Expedia
From $270 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 $270 per night (USD)
VRBO
From $344 per night (USD)
Expedia
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)
Expedia
From $233 per night (USD)
VRBO
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Description: Beautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an ...
From $233 per night (USD)
VRBO
From $291 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 $291 per night (USD)
VRBO
From $456 per night (USD)
VRBO
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 $456 per night (USD)
VRBO
From $231 per night (USD)
Expedia
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 $231 per night (USD)
Expedia
From $313 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 $313 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Oceanfront Home With Large Private Deck with boat dockage
Bedrooms:
2
Bathrooms:
2
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 $415 per night (USD)
Expedia
From $443 per night (USD)
VRBO
44ft Seawall at Sportsman's Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
44ft Seawall at Sportsman's Paradise True Island Paradise. Brand New in the rental program, this 2020 Stilted 2Bd/2Ba ...
From $443 per night (USD)
VRBO
From $356 per night (USD)
Expedia
WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental
Bedrooms:
2
Bathrooms:
2
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 $356 per night (USD)
Expedia

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