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National Key Deer Refuge Rentals

$Dog-Friendly, Canal-Front Home w\/Free WiFi, Central AC, Private W\/D, Boat Access$
From $655 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 $655 per night (USD)
VRBO
$**TURTLE COVE VIEWS @ VENTURE OUT** 2BR\/2BA Cottage +35’ Private Slip | 80’ Pool$
From $419 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 $419 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
House A - You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a fe ...
From $298 per night (USD)
VRBO
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Expedia
Easy access to the Ocean and Gulf
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Leave your worries and enjoy the island life style. I promise you that this will be your favorite gateway. Beautiful san ...
Click For Pricing
Expedia
From $846 per night (USD)
VRBO
Little Torch Key Nest - Ocean view with pool
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitch ...
From $846 per night (USD)
VRBO
$Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry$
From $252 per night (USD)
Expedia
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 $252 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Waterfront Cozy Cottage with Boat Ramp & Dock!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your ...
From $642 per night (USD)
VRBO
From $407 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 $407 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Waterfront home with dock, high-speed WiFi, and central AC - snowbird-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cayo Loco Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $392 per night (USD)
VRBO
From $447 per night (USD)
Expedia
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)
Expedia
From $376 per night (USD)
VRBO
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 $376 per night (USD)
VRBO
From $1779 per night (USD)
Expedia
Waterfront Beach Houses with Dock & Heated Pool!
Bedrooms:
5
Bathrooms:
8
Sleeps:
20
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront homes with 200 foot dock for your boat. Two exclu ...
From $1779 per night (USD)
Expedia
$Captains Quarters - Cudjoe Key - Pool- Waterfront w\/ Boat Dock$
From $532 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 $532 per night (USD)
VRBO
From $411 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 $411 per night (USD)
Expedia
$Beautiful, 2100 sq ft 3\/2 w\/ocean views & easy ocean & gulf access.$
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 $332 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 $332 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
$Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key$
From $230 per night (USD)
Expedia
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 $230 per night (USD)
Expedia
From $220 per night (USD)
VRBO
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)
VRBO
From $2805 per night (USD)
Expedia
A Tropical Luxury Getaway, Your own private resort!!
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
For more pictures on this property look us up on Instagram at sterlingbayhouse. This house is located on the open wate ...
From $2805 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Escape to Eden | Canalfront half-duplex with short run to channel on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean spac ...
From $171 per night (USD)
VRBO
From $594 per night (USD)
Expedia
Oceanside home, dock,kayaks,bikes,pool,fishing,111
Bedrooms:
6
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $594 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,109
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $533 per night (USD)
VRBO
From $507 per night (USD)
Expedia
Oceanside home, dock,kayaks,bikes,pool,fishing,107
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $507 per night (USD)
Expedia
From $512 per night (USD)
VRBO
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 $512 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #14 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $223 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Open water views, New heated & chilled pool. Huge master suite! wraparound decks
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $341 per night (USD)
VRBO
From $306 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
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $306 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community bui ...
From $440 per night (USD)
VRBO
From $346 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 $346 per night (USD)
Expedia
Click For Pricing
VRBO
Affordable, Adorable home waiting for you in Cudjoe Key
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Adorable canal front 2 bed/2 bath home for rent in Cudjoe Key. This indoor/outdoor floor plan is complemented by 3 twelv ...
Click For Pricing
VRBO
$Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise$
From $232 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 $232 per night (USD)
Expedia
$**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool$
From $429 per night (USD)
VRBO
**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 $429 per night (USD)
VRBO
$September Special Rate! Book Now at this canal front pool home\n\n$
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 $538 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 $538 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy 2 Bedroom home in Summerland Key
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our home is located in a quiet and cozy area 5 minutes away from the famous Ramrod Swim Hole; a local treasure. It is al ...
Click For Pricing
Expedia
From $246 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 $246 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the chann ...
From $193 per night (USD)
Expedia
$Casa Playa | 4 bed\/2 bath canalfront getaway on Ramrod Key$
From $239 per night (USD)
VRBO
Casa Playa | 4 bed\/2 bath canalfront getaway on Ramrod Key
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Casa Playa, your spacious 4-bedroom, 2-bathroom retreat nestled in the serene beauty of Ramrod Key. This invi ...
From $239 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $368 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $329 per night (USD)
VRBO
$Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D$
From $225 per night (USD)
Expedia
Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $225 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Vacation like a local
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $248 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 $622 per night (USD)
VRBO
Blue Vacation Home Free Cancellation See Details
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vacation home has a view over Cudjoe Bay to the Atlantic from the common deck and from the private pool deck. 4 bedroom ...
From $622 per night (USD)
VRBO
From $736 per night (USD)
VRBO
White Vacation Home Free Cancellation See Details
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Kayaks come with the rental. Small floating dock for your boat. We have 2 other vacation homes right next to this home i ...
From $736 per night (USD)
VRBO
From $568 per night (USD)
VRBO
Yellow Home FREE PONTOON RENTAL! See details
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you book your stay for the days shown below March 30th - April 15th, 2025 April 23rd - May 3rd, 2025 May 17th - May ...
From $568 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Nader's Vacation Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
From $291 per night (USD)
Expedia
From $284 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 $284 per night (USD)
VRBO
From $309 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 $309 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #13 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. SpaciouQuaint, clean, co ...
From $360 per night (USD)
VRBO
Click For Pricing
Expedia
Pirates Pleasure Fishing and Snorkeling.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Mobile home on boating canal, access to the contents for flats fishing and the Atlantic for deep sea fishing. Property ...
Click For Pricing
Expedia
From $229 per night (USD)
VRBO
Enjoy Caribbean weather in the USA. Openings in May 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 $229 per night (USD)
VRBO
$Group Therapy | 3 bed, 2 bath home w\/ new pool, quick ocean access$
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $1328 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 $1328 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
Click For Pricing
VRBO
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
VRBO
From $297 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 $297 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Bedrooms:
3
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 $349 per night (USD)
VRBO
From $359 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 $359 per night (USD)
Expedia
From $384 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 $384 per night (USD)
VRBO
From $479 per night (USD)
Expedia
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)
Expedia
From $209 per night (USD)
VRBO
The Bent Anchor-boat lift diving snorkeling fishing key deer 22 miles Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to our 3 bedroom, 2 full bath home on canal front Ramrod key. Quite laidback community. Great fishing & diving. ...
From $209 per night (USD)
VRBO
$Summerland Sanctuary: 3BR Canal Front Retreat with Private Pool, Dockage & Premier Boating\/Fishing$
From $261 per night (USD)
Expedia
Summerland Sanctuary: 3BR Canal Front Retreat with Private Pool, Dockage & Premier Boating\/Fishing
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $261 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Canal Front Home in Gated Community. Fun in the Sun #342
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It's Time for some Fun in the Sun here at Venture Out's gated community on Cudjoe Key located at Mile Marker 23 in the F ...
From $588 per night (USD)
VRBO
From $492 per night (USD)
Expedia
**COSTA VIDA @ CUDJOE KEY** Pristine Waterfront Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! COSTA VIDA is ...
From $492 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Keys Living Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Comfortable Cottage in the heart of the Fabulous Florida Keys! Only 30 minutes from Key West and 15 minutes from Bahia H ...
From $137 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Sunny Gens - Venture Out #606
Bedrooms:
2
Bathrooms:
3
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 $382 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Charming 4-bedroom house with WiFi and AC in beautiful Summerland Key
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Sugarloaf Key is waiting for you at this 4-bedroom house. Each bedroom offers a unique sleeping experience with 2 queen ...
From $350 per night (USD)
VRBO
$2 Bedroom Canal Home in Cudjoe Key, FL w\/ Private Pool & Extra Loft Space$
From $329 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 $329 per night (USD)
Expedia
$JULY 2025 DISCOUNT - 3 Bedroom\/2 Bath Canal Home w\/ Private Pool - Cudjoe Key$
From $369 per night (USD)
VRBO
JULY 2025 DISCOUNT - 3 Bedroom\/2 Bath Canal Home w\/ Private Pool - Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Reel Life, a beautiful Cudjoe Gardens Oasis! Located on the ocean side of Cudjoe Key, this home has everythin ...
From $369 per night (USD)
VRBO
From $562 per night (USD)
Expedia
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 $562 per night (USD)
Expedia
From $294 per night (USD)
VRBO
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)
VRBO
From $161 per night (USD)
VRBO
Charming canal front 2-bedroom mobile home with WiFi and AC in Little Torch Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VRBO required we create a new listing after 9 years and 20 perfect 5 star ratings!!! We had the same guests for the pas ...
From $161 per night (USD)
VRBO
From $183 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 $183 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Cozy keys getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Your home away from home in Ramrod Key with 1 bedroom. This wonderful house is equipped with all the essentials for a co ...
From $157 per night (USD)
Expedia
From $55 per night (USD)
VRBO
Charming shared 1-bedroom house with AC and WiFi also has a 37 foot dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Summerland Beauty located 35 min north of Key West. Many charming restaurants located nearby. Plenty of activities and f ...
From $55 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Cozy home with private pool, BBQ, central AC, private dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Salty Air Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $371 per night (USD)
Expedia
From $100 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 $100 per night (USD)
VRBO
From $383 per night (USD)
Expedia
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 $383 per night (USD)
Expedia
From $345 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 $345 per night (USD)
VRBO
From $614 per night (USD)
Expedia
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 $614 per night (USD)
Expedia
From $173 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 $173 per night (USD)
VRBO
From $355 per night (USD)
VRBO
Beautiful 4 bedroom 2.5 bath pool home with great boating
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful and cozy 4 bedroom, pool home located on Cudjoe key with excellent boating access to the Atlantic or the Gulf. ...
From $355 per night (USD)
VRBO
From $149 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 $149 per night (USD)
VRBO
From $183 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 $183 per night (USD)
VRBO
From $600 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 $600 per night (USD)
VRBO
From $215 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 $215 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Charming 2-bedroom house on Little Torch Key with pool and tiki bar- 28 DAY MIN.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your perfect getaway in Little Torch Key, Florida! Nestled on a peaceful canal, this charming 2-bedroom, 2-ba ...
From $256 per night (USD)
VRBO
From $811 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 $811 per night (USD)
Expedia
From $2130 per night (USD)
VRBO
Luxurious 6 Bedroom 8 Bath Open water pool home on Ramrod Key with great boating
Bedrooms:
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 $2130 per night (USD)
VRBO
From $283 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 $283 per night (USD)
VRBO
From $147 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 $147 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Canal Front Home in Gated Community. Salt Life #182
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Live the Salt Life #182 here at Venture Out. in a gated community on Cudjoe Key located at Mile Marker 23 in the Florida ...
From $306 per night (USD)
Expedia
From $253 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 $253 per night (USD)
VRBO
From $249 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 $249 per night (USD)
VRBO
From $124 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 $124 per night (USD)
VRBO
$2bed\/2bath Summerland Key Canal front perfection with pool$
From $372 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 $372 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Welcome to Paradise Palms Home 3BD,2BA waterfront, pool & dock in Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in the lower Florida Keys and close to the iconic Bahia Honda State Park Beach you could escape and enjoy a peac ...
From $332 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Divers Den - Gorgeous Florida Keys Canal Home -Sunset views of the Salt Ponds
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our luxurious canal-front retreat in a private and serene location, offering the perfect blend of comfort and ...
From $317 per night (USD)
VRBO

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