Summerland Key Rentals
From $1297 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
"THE POOL MAY BE HEATED FOR AN ADDITIONAL FEE OF $25 PER DAY OF STAY" This is a newly remodeled four bedrooms elegant ho ...
From $1297 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 $186 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 $186 per night (USD)VRBO
From $187 per night (USD)Expedia
Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the laid-back beauty of Summerland Key at this charming canal-front retreat, designed for boating, fishing, an ...
From $187 per night (USD)Expedia
From $315 per night (USD)VRBO
Canalfront house with private pool, WiFi, private washer/dryer, and central AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
With three separate living areas and a private heated pool, this charming home is full of comfortable spaces for guests ...
From $315 per night (USD)VRBO
From $923 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 $923 per night (USD)Expedia
From $301 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 $301 per night (USD)VRBO
From $701 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 $701 per night (USD)Expedia
From $244 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 $244 per night (USD)VRBO
From $536 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 $536 per night (USD)VRBO
From $1965 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 $1965 per night (USD)VRBO
From $381 per night (USD)VRBO
Fishermens' dream B.Y.O. boat ocean front with protected canal 600' to bluewater
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is an oceanfront vacation rental in the world-famous Florida Keys on secluded southern end of Summerland Key, mile ...
From $381 per night (USD)VRBO
From $736 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 $736 per night (USD)VRBO
From $355 per night (USD)Expedia
PALM COTTAGE - Sleeps 4 summer fun ..lobster season.
- 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 $355 per night (USD)Expedia
From $1177 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 $1177 per night (USD)VRBO
From $611 per night (USD)Expedia
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 $611 per night (USD)Expedia
From $673 per night (USD)VRBO
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 $673 per night (USD)VRBO
From $520 per night (USD)Expedia
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
🏡 Amenities: Dock, Guest Cottage, Pool, Spa, Outdoor Kitchen, Firepit 🌊 Kayaks, and Paddle Boards 📍 30 Minutes to K ...
From $520 per night (USD)Expedia
From $332 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 $332 per night (USD)VRBO
From $590 per night (USD)Expedia
Ocean Breeze House - Summer fun Sleeps 8 boating, 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 $590 per night (USD)Expedia
From $270 per night (USD)VRBO
SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster
- 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 $270 per night (USD)VRBO
From $653 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 $653 per night (USD)VRBO
From $304 per night (USD)VRBO
Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season.
- 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 $304 per night (USD)VRBO
From $188 per night (USD)Expedia
Ground Level Home With Deepwater Canal And 30' Of Dock Space
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first can ...
From $188 per night (USD)Expedia
From $396 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 $396 per night (USD)VRBO
From $703 per night (USD)VRBO
Waterfront Sunrise & Sunset Full Views! Pool, dock, lift, 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 $703 per night (USD)VRBO
From $679 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 $679 per night (USD)VRBO
From $325 per night (USD)Expedia
FLAMINGO COTTAGE summer fun. Pool, boating, fishing lobster season.
- 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 $325 per night (USD)Expedia
From $626 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 $626 per night (USD)VRBO
From $304 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 $304 per night (USD)VRBO
From $275 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! VACANT LOT ONLY...MUST BRING YOUR OWN RV 35' Dockage with Tropical Lan ...
From $275 per night (USD)VRBO
From $393 per night (USD)Expedia
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 $393 per night (USD)Expedia
From $412 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 $412 per night (USD)VRBO
From $392 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 $392 per night (USD)Expedia
From $526 per night (USD)VRBO
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 $526 per night (USD)VRBO
From $307 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 $307 per night (USD)Expedia
From $584 per night (USD)VRBO
Waterfront home with boat/canal access, screened lanai, & renovated interior
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Everything you need for a carefree Florida Keys escape is right at your fingertips in this laid-back bungalow. Boasting ...
From $584 per night (USD)VRBO
From $320 per night (USD)Expedia
Oceanfront Home w/ Dock, Kayak & Beach Area
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sunset Beach, a stunning 4 bedroom, 5.5 bathroom waterfront retreat designed for those looking to experience ...
From $320 per night (USD)Expedia
From $516 per night (USD)VRBO
Open Water Retreat with 58' Seawall, Kayaks, Paddleboards, Bikes & Panoramic Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Palm Paradise #477, a true Florida Keys escape located directly on the open ocean. This waterfront retreat fe ...
From $516 per night (USD)VRBO
From $1196 per night (USD)Expedia
Spacious 7-bedroom estate with AC in peaceful Summerland Key
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Your cozy getaway awaits in Summerland Key at this wonderful estate. With seven spacious bedrooms, including four king b ...
From $1196 per night (USD)Expedia
From $504 per night (USD)VRBO
BEAUTIFUL RENTAL OPEN WATER in Summerland Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to this house in picturesque Summerland Key. With three spacious bedrooms, each featuring a comfortable queen bed ...
From $504 per night (USD)VRBO
From $604 per night (USD)Expedia
Waterfront Venture Out Retreat w/ 35' Dock, Kayaks & Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Waterfront 2BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing Welcome to Conch Shell — your relaxing w ...
From $604 per night (USD)Expedia
From $511 per night (USD)VRBO
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Conch Hideaway #423, an affordable getaway near Key West-located inside the private, gated community of Ventu ...
From $511 per night (USD)VRBO
From $640 per night (USD)Expedia
Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your Florida Keys escape, a beautifully situated 2-bedroom, 2-bath waterfront home in the gated Venture Out c ...
From $640 per night (USD)Expedia
From $459 per night (USD)VRBO
Waterfront 2BR Marina Basin Home with 35' Dock, Balcony & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront 2BR in Venture Out with 35' Dock, Pool & Incredible Ocean Views Welcome to Tipsy Tiki #374, a charming 2 bedr ...
From $459 per night (USD)VRBO
From $426 per night (USD)Expedia
Waterfront 2BR in Venture Out with 35' Dock, Pool & Marina Basin Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront 2BR in Venture Out with 35' Dock, Pool & Breathtaking Views Welcome to Oceanfront Oasis #373, a beautiful 2 b ...
From $426 per night (USD)Expedia
From $877 per night (USD)VRBO
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover elevated coastal living at Coconut Telegraph #221, a beautifully updated 2-bedroom, 2-bath waterfront retreat n ...
From $877 per night (USD)VRBO
From $427 per night (USD)Expedia
Casa Key Lime VO291 Bring your boat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CASA KEY LIME - VO291 BRING YOUR BOAT 35' Dockage Open Water Views! Stilt 2Bd/2Ba, Free WiFi! Walk to Pool!Beautiful 2B ...
From $427 per night (USD)Expedia
From $613 per night (USD)VRBO
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautifully updated and coastally designed 2-bedroom, 2-bath home is perfectly situated on a canal with breathtakin ...
From $613 per night (USD)VRBO
From $364 per night (USD)Expedia
Canalfront Keys Home - 70' Dock, Large Porch, Pool & Quick Access to Open Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BIG BOATS WELCOME! Waterfront 2BR in Venture Out with 70' Dock, Gated Community, Pool & World-Class Fishing Welcome to B ...
From $364 per night (USD)Expedia
From $378 per night (USD)VRBO
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 $378 per night (USD)VRBO
From $369 per night (USD)Expedia
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 $369 per night (USD)Expedia
From $398 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 $398 per night (USD)VRBO
From $422 per night (USD)Expedia
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 $422 per night (USD)Expedia
From $222 per night (USD)VRBO
Canal-Front Gem w/ Peekaboo Views in Cudjoe Key!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spectacular Sunsets & Bay View | Waterfront Lounge Area | 2 Kayaks Planning a long-term stay in the Florida Keys? Book ...
From $222 per night (USD)VRBO
From $425 per night (USD)Expedia
NAUTICAL NEST - 3-bedroom canal front tranquil home on Summerland Key with AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
NAUTICAL NEST – Your Waterfront Escape in the Florida Keys Welcome to Nautical Nest, a beautifully appointed 3-bedroom, ...
From $425 per night (USD)Expedia
From $683 per night (USD)VRBO
Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wastin' Away Again #468 is your perfect Florida Keys escape - a beautifully appointed 2 bedroom, 2 bathroom waterfront r ...
From $683 per night (USD)VRBO
From $214 per night (USD)VRBO
Stunning water views RV lot with full hookups paved patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy stunning open water views from RV Lot #378, a well-maintained dry RV lot located in a prime Florida Keys setting. ...
From $214 per night (USD)VRBO
From $151 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 $151 per night (USD)VRBO
From $308 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 $308 per night (USD)VRBO
From $903 per night (USD)VRBO
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Oceanfront 2BR Retreat in Venture Out with Stunning Views, 32' Dock, Heated Pool & Optional Golf Cart Welcome to Caribbe ...
From $903 per night (USD)VRBO
From $300 per night (USD)Expedia
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, 2 ...
From $300 per night (USD)Expedia
From $448 per night (USD)VRBO
Ocean View High-Rise in Venture Out | Pool, Boat Ramp & close to Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Casa Kiwi #472, your perfect getaway in the heart of the beautiful Florida Keys. Nestled on a serene interior ...
From $448 per night (USD)VRBO
From $372 per night (USD)Expedia
Island Home in Paradise #624 - OCEANFRONT Community!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Island Cottage Retreat in Venture Out - Pet-Friendly 2BR, Lots of Amenities & Private Patio Welcome to Island Home in Pa ...
From $372 per night (USD)Expedia
From $240 per night (USD)VRBO
Waterfront RV Lot #574, 35' Seawall, Boat Dockage, Pool & Venture Out Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your recreational slice of paradise in the Florida Keys. RV lot #574 is nestled in the vibrant community of C ...
From $240 per night (USD)VRBO
From $214 per night (USD)VRBO
Private RV Lot w/ 20' Seawall (17' Boat Max) | Pool, Marina & Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your Florida Keys escape at RV Lot #239 inside the gated community of Venture Out on Cudjoe Key. This recreat ...
From $214 per night (USD)VRBO
From $228 per night (USD)VRBO
Canal-Front RV Lot w/ 35' Seawall, Shade Tree, Picnic Table & Storage – Boat-Friendly Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your Florida Keys getaway at RV Lot #551, located inside the gated community of Venture Out on Cudjoe Key. Th ...
From $228 per night (USD)VRBO
From $228 per night (USD)VRBO
Private Tropical RV Lot #405 | Paved Pad, Palms, Seating for 6 & Full Hookups
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your Florida Keys getaway at RV Lot #405, located inside the gated community of Venture Out on Cudjoe Key. Th ...
From $228 per night (USD)VRBO
From $208 per night (USD)VRBO
RV Lot #474 in Venture Out | 30/50 Amp | Bring Your RV | No RV Included
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your Florida Keys escape at RV Lot #474 inside the gated community of Venture Out on Cudjoe Key. This recreat ...
From $208 per night (USD)VRBO
From $395 per night (USD)Expedia
Tropical Island Paradise W / Open Water Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please see our other property if you do not see your dates available! Property # 2092236 https://www.vrbo.com/2092236?ad ...
From $395 per night (USD)Expedia
From $376 per night (USD)VRBO
Sun Bake @ Sponge Cake, 64' Sea Wall,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Canal front home in a gated resort community. There is a $125 resort fee and parking for one vehicle at the property. T ...
From $376 per night (USD)VRBO
From $602 per night (USD)Expedia
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Coastal 2BR Retreat in Venture Out with Heated Pool, Boat Ramp & Close to Key West Welcome to Blue Lobster Lodge #543, y ...
From $602 per night (USD)Expedia
From $319 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 $319 per night (USD)VRBO
From $236 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 $236 per night (USD)VRBO
From $230 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 $230 per night (USD)VRBO
From $438 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 $438 per night (USD)Expedia
From $443 per night (USD)VRBO
Endless Water Views - Venture Out 526
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Endless Water Views - Venture Out 526 Newer Stilted 2Bd/2Ba Home with WIFI 35' Dockage Open Water Views! This newer cons ...
From $443 per night (USD)VRBO
From $245 per night (USD)VRBO
Canal Front Home Access to Kemp Channel Cudjoe Key New POOL!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfect fishing and boating location on Kemp Channel between Cudjoe Key and Summerland Key. New Pool Installed August ...
From $245 per night (USD)VRBO
From $443 per night (USD)VRBO
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Shangri-la in the Keys! Enjoy the water views and a 45' dock space! VO unit 413 - 2Bd/2Ba Stilt Home Newly renovated s ...
From $443 per night (USD)VRBO
From $328 per night (USD)Expedia
Treasure Isle at Parks End - Venture Out 062
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Treasure Isle at Parks End - Venture Out 062 Southern Location Walk to Ocean! This sparkling clean and bright 2 Bedroom ...
From $328 per night (USD)Expedia
From $443 per night (USD)VRBO
Piece Of Eight - Venture Out 279
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Piece Of Eight - Venture Out 279 Stilt 2Bd/2Ba 35' Dockage Close to Everything! Recently updated 2 BR/2 BA stilt home ...
From $443 per night (USD)VRBO
From $549 per night (USD)Expedia
Mad Mahi Canal with pool.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atl ...
From $549 per night (USD)Expedia
From $391 per night (USD)VRBO
Sea La Vie - Your Oceanfront Escape - 3BD/3Bath - Cudjoe Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sea La Vie: Oceanfront Vacation Rental in Cudjoe Key, Florida Looking for the perfect oceanfront getaway in the Florida ...
From $391 per night (USD)VRBO
From $520 per night (USD)Expedia
SOUTHERN SUNSET - As seen on House Hunters-S228 E6 - Family Time in the FL Keys
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 ...
From $520 per night (USD)Expedia
From $624 per night (USD)VRBO
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 $624 per night (USD)VRBO
From $427 per night (USD)Expedia
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 $427 per night (USD)Expedia
From $373 per night (USD)VRBO
Sunset Serenity – Open Water Paradise | Dockage, Sunset Views, Dog Friendly & Minutes to Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sunset Serenity – Your Open Water Paradise in the Lower Florida Keys! Wake up to breathtaking open water ...
From $373 per night (USD)VRBO
From $259 per night (USD)Expedia
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 $259 per night (USD)Expedia
From $570 per night (USD)VRBO
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 $570 per night (USD)VRBO
From $464 per night (USD)Expedia
**DOLPHIN DAYDREAMS @ VENTURE OUT** New Home + Last Key White Glove Service...
- 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 $464 per night (USD)Expedia
From $637 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 $637 per night (USD)VRBO
From $597 per night (USD)Expedia
Summerland Serenity – Elevated Waterfront Luxury with Private Elevator & Pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Summerland Serenity – Elevated Waterfront Luxury with Private Elevator & Pool Welcome to Summerland Serenity, an except ...
From $597 per night (USD)Expedia
From $491 per night (USD)VRBO
Mariner's Nook #484 Oceanfront Escape with 50' Dock, Pool & Panoramic Florida Keys Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront Corner-Lot Retreat in Venture Out with 50' Dock, Panoramic Water Views & Heated Pool - Big Boats Welcome Welc ...
From $491 per night (USD)VRBO
From $873 per night (USD)Expedia
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 $873 per night (USD)Expedia
From $374 per night (USD)VRBO
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 $374 per night (USD)VRBO
From $254 per night (USD)Expedia
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 $254 per night (USD)Expedia
From $173 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 $173 per night (USD)VRBO
From $173 per night (USD)Expedia
430 Empty RV Lot with 35' Seawall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Empty Waterfront RV Lot just waiting for you to come visit the beautiful Florida Keys. Private 35-foot seawall with acce ...
From $173 per night (USD)Expedia
From $180 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 $180 per night (USD)VRBO
From $428 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 $428 per night (USD)Expedia