National Key Deer Refuge Rentals
From $249 per night (USD)VRBO
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 $249 per night (USD)VRBO
From $2675 per night (USD)Expedia
A Tropical Luxury Getaway, Your own private resort!!
- Bedrooms:
- 6
- 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 $2675 per night (USD)Expedia
From $328 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 $328 per night (USD)VRBO
From $333 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 $333 per night (USD)Expedia
From $362 per night (USD)VRBO
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Residential Condominium! Is located on a 60' wide canal ...
From $362 per night (USD)VRBO
From $336 per night (USD)Expedia
Amazing Pool & Canal Ground Level Home, Ocean access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is an amazing Ground level Pool and Canal home. With stunning concrete ground pool and Jacuzzi tub. (POOL HEAT AV ...
From $336 per night (USD)Expedia
From $235 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 $235 per night (USD)VRBO
From $225 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 $225 per night (USD)Expedia
From $455 per night (USD)VRBO
Reel Caribbean Getaway | Newly renovated, great pool & boating access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury Waterfront Living on Summerland Key Escape to the Florida Keys and indulge in island living at its finest in thi ...
From $455 per night (USD)VRBO
From $201 per night (USD)Expedia
Cedar Cottage | Adorable canalfront cottage, lots of dockage on Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect slice of paradise in the heart of the Florida Keys! This newly remodeled 2 bed/2 bath home on a ...
From $201 per night (USD)Expedia
From $274 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 $274 per night (USD)VRBO
From $277 per night (USD)VRBO
POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. Oceanfro ...
From $277 per night (USD)VRBO
From $243 per night (USD)VRBO
2 Bedroom/3 Bath Waterfront 28 day rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
The Crab House 28 day rental offers 2 spacious bedrooms 3 bathrooms (1 full bath in garage to use after coming in from b ...
From $243 per night (USD)VRBO
From $196 per night (USD)Expedia
Getaway to the Quiet Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom, 2 Bathroom with Hot Tub & Large Boat Dock This is a beautiful 2 bedroom, 2 bathroom house located in quiet Cu ...
From $196 per night (USD)Expedia
From $235 per night (USD)VRBO
New listing 3bd/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Bridge restriction***BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a ...
From $235 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 $248 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 $248 per night (USD)VRBO
From $205 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 $205 per night (USD)VRBO
From $1800 per night (USD)VRBO
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 $1800 per night (USD)VRBO
From $675 per night (USD)VRBO
2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our cozy 2 bedroom 2 bath 2 story home with a private pool offers a vacation to remember in the Lower Keys. Located in L ...
From $675 per night (USD)VRBO
From $457 per night (USD)VRBO
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Captain’s Quarters — Your Waterfront Escape on Beautiful Cudjoe Bay Discover the perfect blend of comfort, l ...
From $457 per night (USD)VRBO
From $225 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 $225 per night (USD)VRBO
From $417 per night (USD)VRBO
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 $417 per night (USD)VRBO
From $479 per night (USD)VRBO
Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
You have found it. So quiet. So beautiful. On Bogie Channel. One mile from No Name Pub. Only 30 miles from Key West! FU ...
From $479 per night (USD)VRBO
From $163 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 $163 per night (USD)VRBO
From $528 per night (USD)Expedia
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 $528 per night (USD)Expedia
From $332 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 $332 per night (USD)VRBO
From $812 per night (USD)VRBO
Oasis - Ocean front with pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Oasis is a spacious ocean front property with spectacular views and a large swimming pool with 10 foot overflow spa. T ...
From $812 per night (USD)VRBO
Click For PricingVRBO
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 PricingVRBO
From $186 per night (USD)VRBO
Waterfront beach house with boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $635 per night (USD)VRBO
NAUTILUS...ocean front cottage retreat ~
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nautilus... ocean front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll nee ...
From $635 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 $273 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 $273 per night (USD)VRBO
From $294 per night (USD)VRBO
LATITUDE ADJUSTMENT
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $294 per night (USD)VRBO
From $455 per night (USD)VRBO
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Main House - You're in the tropics... listen to the waves, rest, relax or fish, and snorkel. Spacious three bedroom, two ...
From $455 per night (USD)VRBO
From $286 per night (USD)Expedia
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 $286 per night (USD)Expedia
From $555 per night (USD)VRBO
Private water front property with ocean access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful 15,000 sq ft water front property. Steps away from the famous No Name Pub. Steps away from the no name bridg ...
From $555 per night (USD)VRBO
From $1120 per night (USD)Expedia
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
As featured on the TV Show; Selling Coastal, Vista de Sirenas translates to ‘Mermaid Views’ is a piece of paradise with ...
From $1120 per night (USD)Expedia
From $445 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 $445 per night (USD)VRBO
From $376 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 $376 per night (USD)Expedia
Click For PricingVRBO
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 PricingVRBO
From $240 per night (USD)Expedia
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $240 per night (USD)Expedia
From $236 per night (USD)VRBO
Dates available Oct, Nov, Dec 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2/2Come and enjoy this newly renovated home. Be the first to enjoy! Located in one of the best fishing spots in the Flor ...
From $236 per night (USD)VRBO
From $336 per night (USD)Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #12 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $336 per night (USD)Expedia
From $412 per night (USD)VRBO
Open Water Views - Venture Out Unit 373
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO373 Ocean Views 35' Dockage / MONTHLY RENTALS ONLY FOR JAN/FEB/MARCH Located in the Marina Basin If you are looking fo ...
From $412 per night (USD)VRBO
From $561 per night (USD)Expedia
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This newly remodeled home overlooks the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community bui ...
From $561 per night (USD)Expedia
From $390 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 $390 per night (USD)VRBO
From $220 per night (USD)Expedia
ISLAND PARADISE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We have central air,1 bedroom, 1 bathroom with fully stocked kitchen, washer and dryer, dishwasher, toaster, keurig duo ...
From $220 per night (USD)Expedia
From $407 per night (USD)VRBO
Amazing Open Water Views - Venture Out Unit #374
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $407 per night (USD)VRBO
From $530 per night (USD)Expedia
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VO093 OCEANFRONT GEM! TRUE SOUTHERN EXPOSURE STILT 2BD/2BA 35' SEAWALL Enjoy breathtaking panoramic ocean views from th ...
From $530 per night (USD)Expedia
From $241 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 $241 per night (USD)VRBO
From $335 per night (USD)Expedia
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 $335 per night (USD)Expedia
From $233 per night (USD)VRBO
Panoramic Ocean Front! Venture Out Unit 522
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VO522 Panoramic Ocean Front! 42' Boat Dockage!Beautiful light and bright vacation rental overlooks the most breathtaking ...
From $233 per night (USD)VRBO
From $178 per night (USD)Expedia
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom 2 bath stilt home with large screened in porch overlooking canal and lush tropical coconut palms. Boat dock Wi ...
From $178 per night (USD)Expedia
From $783 per night (USD)VRBO
Latitudes - Ocean front with salt water pool.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There ...
From $783 per night (USD)VRBO
From $555 per night (USD)Expedia
REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Ultimate Florida Keys Escape at Reel Escape — Your Spacious 4-Bedroom Summerland Key Retreat Nestled in ...
From $555 per night (USD)Expedia
From $177 per night (USD)VRBO
Waterfront home with boat dock, 2 kayaks, 2 bikes, AC & W/D - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunset Villa Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $177 per night (USD)VRBO
From $295 per night (USD)Expedia
FL Keys Cottage with Ocean Views - Venture Out Unit 395
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Island Oasis! Tropical Breezes Across from the Marina! A perfect oasis with beautiful views all day, every day. ...
From $295 per night (USD)Expedia
From $252 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 $252 per night (USD)VRBO
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
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PARADISE IN YOUR HANDS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful clean and spacious home. Relax on your deck or take your boat out, canal goes out to the gulf or ocean to do s ...
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From $689 per night (USD)Expedia
Private Secluded Ocean View & Pool Near Key West
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful Eco-friendly Ocean view home is away from the hustle-bustle of Key West. Welcome to this luxury deluxe va ...
From $689 per night (USD)Expedia
From $834 per night (USD)VRBO
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 $834 per night (USD)VRBO
From $223 per night (USD)VRBO
Newly Remodeled Corner House on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
There’s no better place to experience the laid-back calm of the Florida Keys than this bright and newly-remodeled two-be ...
From $223 per night (USD)VRBO
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 $492 per night (USD)Expedia
Beautiful Family Big Pine Retreat! Short drive to Key West!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Big Pine Key offers the most peace & tranquility of the FL Keys! This home offers plenty of space and parking along side ...
From $492 per night (USD)Expedia
From $240 per night (USD)VRBO
Big Pine Key Paradise Canal front fenced yard.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WINTER 2026 OPEN Canal front fenced in home w/dock, boat ocean access. 28 Night Min Stay, WiFi Full kitchen Fully furn ...
From $240 per night (USD)VRBO
From $632 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 $632 per night (USD)VRBO
From $519 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 $519 per night (USD)VRBO
From $533 per night (USD)Expedia
Blue Palms w/boat dock and saltwater pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded ...
From $533 per night (USD)Expedia
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 $651 per night (USD)VRBO
Water View Town home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bd townhomes offer br ...
From $651 per night (USD)VRBO
From $485 per night (USD)VRBO
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Torchview Lookout – Your Private Waterfront Retreat! Escape to paradise at Torchview Lookout, a secluded 3-b ...
From $485 per night (USD)VRBO
From $286 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 $286 per night (USD)Expedia
Click For PricingVRBO
Easy access to the Ocean and Gulf
- Bedrooms:
- 2
- 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 PricingVRBO
From $184 per night (USD)Expedia
Secluded Hideaway with private pool and canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This home is tastefully decorated with a tropical feel. There is a Flat screen TV, high speed internet, central air, an ...
From $184 per night (USD)Expedia
From $362 per night (USD)VRBO
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 $362 per night (USD)VRBO
From $386 per night (USD)VRBO
Casa de Sueno: Boating, Pool | 5 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful & well-appointed 5 bedroom / 2.5 bathroom home & a NEW outdoor shower! Excellent water access on Little Torch ...
From $386 per night (USD)VRBO
From $754 per night (USD)VRBO
Conch House - Ocean front with dock and pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Conch House is located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard! ...
From $754 per night (USD)VRBO
From $447 per night (USD)Expedia
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy ...
From $447 per night (USD)Expedia
From $396 per night (USD)VRBO
Mermaid House! Pool, Dockage, Outdoor Bar!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great centr ...
From $396 per night (USD)VRBO
From $846 per night (USD)Expedia
Little Torch Key Nest - Ocean view with pool
- Bedrooms:
- 4
- 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)Expedia
From $398 per night (USD)VRBO
Beachside @ Torchview Waterfront Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Beachside at Torchview Located on the serene shores of Big Torch Key in the Florida Keys Beachside at Torchv ...
From $398 per night (USD)VRBO
From $310 per night (USD)Expedia
10 minutes away from Bahia Honda and 30 minutes away from Key West
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Outside you will find hammocks to relax in, bikes to check out the area and a dock that will accommodate most type boat. ...
From $310 per night (USD)Expedia
From $224 per night (USD)VRBO
Relaxing and Inviting home in gated community
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in ta ...
From $224 per night (USD)VRBO
From $414 per night (USD)VRBO
Beautiful House on Ramrod Key with boat slip and easy water access.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The house is very spacious. Large front & back decks. Newer furniture through-out. The house is on a lagoon and you can ...
From $414 per night (USD)VRBO
From $281 per night (USD)VRBO
Cottage with Pool and Dockage, just minutes to Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #4 - Quaint, clean, comfortable cottage just 20 miles from Key West. Cottage offers a full kitchen, large screen ...
From $281 per night (USD)VRBO
From $388 per night (USD)VRBO
\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
SEA ESCAPE This two story home with breathtaking full views of the crystalline Atlantic Ocean is part of Sunrise Beach ...
From $388 per night (USD)VRBO
From $715 per night (USD)VRBO
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
GREAT SNORKELING UNDER DOCK. FISH FROM DOCK TOO. OUR PICTURES OF THE HOUSE ARE AFTER IRMA OUR DOCK SURVIVED WITHOUT A S ...
From $715 per night (USD)VRBO
From $224 per night (USD)Expedia
Lovely Canal Front Big Pine Key House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Canal front house in a quit peaceful neighborhood. South of Marathon <20-30 min> and North of Key West <40 min aprox. U ...
From $224 per night (USD)Expedia
From $207 per night (USD)VRBO
SHANGRI-LA Sept Special Rates
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to 'Shangri-La' This is where you can RELAX and ENJOY the TRANQUIL beauty of the sun, sea & sand of the Florida ...
From $207 per night (USD)VRBO
From $601 per night (USD)VRBO
Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This luxurious Cudjoe Key vacation rental home, located directly on a sandy beach overlooking the crystalline Atlantic O ...
From $601 per night (USD)VRBO
From $638 per night (USD)VRBO
Tropical Paradise - Ocean front with swim spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and roman ...
From $638 per night (USD)VRBO
From $372 per night (USD)Expedia
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. ...
From $372 per night (USD)Expedia
From $253 per night (USD)VRBO
Charming cottages, dockage, pool, just minutes to Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #6 - Only 20 miles from Key West, but a world away from the hustle and bustle. Come experience a truly relaxing ...
From $253 per night (USD)VRBO
From $366 per night (USD)Expedia
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 $366 per night (USD)Expedia
From $765 per night (USD)VRBO
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)VRBO
From $636 per night (USD)Expedia
Starfish - Ocean front with dock and pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Starfish House - Dock your boat at your back door 3 bedroom 2 bath ocean front home with pool This home is a GEM. Very ...
From $636 per night (USD)Expedia
From $186 per night (USD)VRBO
Ocean Front Access - just 30 miles to Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer, public ramp just around ...
From $186 per night (USD)VRBO
From $2092 per night (USD)VRBO
CASA AQUA - 16 Acre Open Water Spanish Style Casual Elegance
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 15
This island oasis called CASA AQUA is a 16 acre Spanish Mediterranean estate on the Atlantic Ocean in the Lower Florida ...
From $2092 per night (USD)VRBO