National Key Deer Refuge Rentals
From $238 per night (USD)VRBO
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 $238 per night (USD)VRBO
From $319 per night (USD)Expedia
Charming 3-bedroom house with Tiki Hut ,WiFi and AC in gorgeous Summerland Key,,
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this lovely house in picturesque Summerland Key. This charming property features 3 bedrooms - one with a twin ...
From $319 per night (USD)Expedia
From $367 per night (USD)VRBO
Fishermans Paradise@The Pointe on Summerland Key 2Bed/2Bath, Pool, 120' of Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Fishermans Paradise @ The Pointe on Summerland Key in the Fabulous Florida Keys. Fishermans Paradise @ The Po ...
From $367 per night (USD)VRBO
From $215 per night (USD)Expedia
Rv empty lot campground in Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Discover the beauty of CudJoe Key from this Rv Lot campground. Nestled in a serene setting, this welcoming retreat offer ...
From $215 per night (USD)Expedia
From $264 per night (USD)VRBO
SEA COVE ~ Canal Front 2 BR/2 Ba Home in Cudjoe Key w/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
LOWER KEYS WATER WORLD… Come on down to some of the most beautiful natural vistas and the serene environment of Cudjoe K ...
From $264 per night (USD)VRBO
From $290 per night (USD)Expedia
FLORIDA KEYS PARADISE! DEEP WATER CANAL WITH FAST OCEAN ACCESS.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Carribean Paradise is a beautiful 3 bedroom 3 bathroom house in a quiet, beautiful neighborhood. Large corner lot with ...
From $290 per night (USD)Expedia
From $440 per night (USD)VRBO
ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DREAM COASTAL RETREAT… If dazzling open waters and deep draft boating and dockage is what you crave, look no further. We ...
From $440 per night (USD)VRBO
From $337 per night (USD)Expedia
Canal front with open water views in Venture Out - Lot 529
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront Getaway in Venture Out Welcome to your perfect getaway! This beautifully updated vacation home offers comfor ...
From $337 per night (USD)Expedia
From $448 per night (USD)VRBO
Sunset Serenity – 3BR Open Water Oasis On Summerland Key Boat Dockage, Stunning Views & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sunset Serenity – Your Open Water Escape in the Lower Keys! Unwind in paradise at Sunset Serenity, a stunnin ...
From $448 per night (USD)VRBO
From $441 per night (USD)Expedia
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 $441 per night (USD)Expedia
From $428 per night (USD)VRBO
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 $428 per night (USD)VRBO
From $294 per night (USD)Expedia
Charming Conch Cottage on deep water canal in Little Torch Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Little Torch Key is waiting for you at this 3-bedroom house. Bring your fishing poles and snorkel gear! This phenomenal ...
From $294 per night (USD)Expedia
From $950 per night (USD)VRBO
Luxury 5BR/5.5BA Open Water Pool Home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Experience the ultimate Florida Keys escape in this brand-new 5-bedroom, 5.5-bath luxury pool home on the open water of ...
From $950 per night (USD)VRBO
From $173 per night (USD)VRBO
RV Lot 377 Venture Out, Waterfront Retreat, Accommodates large/oversized RVs
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This RV lot is a prime waterfront retreat, featuring a lushly landscaped setting that provides both privacy and natural ...
From $173 per night (USD)VRBO
From $164 per night (USD)VRBO
Charming Canal-Front 2/1 Getaway on Ramrod Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Charming Canal-Front Getaway on Ramrod Key Escape to this cozy 2-bedroom, 1-bath fishing cottage, perfectly situated in ...
From $164 per night (USD)VRBO
From $197 per night (USD)VRBO
Oversized RV Lot with 41'+12' Seawall, Deep Water Access, and Stunning Open Water Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your slice of paradise in the Florida Keys. This exceptional open-water RV lot is located in the desirable ga ...
From $197 per night (USD)VRBO
From $196 per night (USD)VRBO
Stunning Open Water RV Lot with 38' Seawall and Great Amenities in Gated Community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your perfect Florida Keys getaway. This stunning RV lot is located directly on the open water, offering unint ...
From $196 per night (USD)VRBO
From $285 per night (USD)VRBO
The Tree-House: Tropical getaway in a lush private jungle property!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the woods of Little Torch Key, this exquisite tree-house style cottage offers complete privacy from the outsi ...
From $285 per night (USD)VRBO
From $245 per night (USD)VRBO
Secluded Waterfront Oasis in the Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our secluded home on No Name Key is just right for nature lovers. Surrounded by trees and located on the canal, you'l ...
From $245 per night (USD)VRBO
From $237 per night (USD)VRBO
Latitude Adjustment #598, Canal front-Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Need a “LATITUDE ADJUSTMENT”? This spotless 2 BR, 2 BA stilt home on a 60' wide canal in Venture Out at MM23, on Cudjoe ...
From $237 per night (USD)VRBO
From $331 per night (USD)VRBO
Good Times & Tan Lines - 3 Bedroom Beautiful Pool Home with boating access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Good Times & Tan Lines - Come sit poolside at this beautiful canal-side Retreat: Your Perfect Island Getaway! Welcome to ...
From $331 per night (USD)VRBO
From $272 per night (USD)VRBO
3/2 on the Water in Paradise Monthly Rental 28 Day min.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wonderful, open concept, 3/2 stilt, canal front home in Summerland Key. On the beautiful, blue/green flow through canal ...
From $272 per night (USD)VRBO
From $833 per night (USD)VRBO
Post Card Point #319 - Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing Waterfront Getaway Overlooking the Marina with Stunning Ocean Views! Welcome to your perfect getaway! This beau ...
From $833 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 $650 per night (USD)VRBO
Sailfish Haven #390 - Ocean Views, 35' seawall
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Florida Keys Waterfront Retreat with Stunning Ocean Views Welcome to your perfect getaway! This beautiful 2-bedroom, 2- ...
From $650 per night (USD)VRBO
From $231 per night (USD)VRBO
Florida Keys Home 20 minutes from Key West with deep water access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful home with three bedrooms, two full bathrooms, screened in deck, waterfront located on canal. Deep water access ...
From $231 per night (USD)VRBO
From $164 per night (USD)VRBO
RV Lot 442 Venture Out, Canal Front, 35ftx69ft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to RV Lot 442 in the exclusive gated community of Venture Out, located in stunning Cudjoe Key, Florida! This spa ...
From $164 per night (USD)VRBO
From $392 per night (USD)VRBO
Waterfront Pool Home w/ Dock – Easy Access to Looe Key & Island Adventures!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover Your Ideal Florida Keys Getaway at Latitudes and Attitudes Welcome to Latitudes and Attitudes, a charming 3-be ...
From $392 per night (USD)VRBO
From $726 per night (USD)VRBO
Stunning 4 Bedroom 5.5 Bath pool home with Sunset Views!!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to 333 Indies Rd! This 4 bedroom 5 and half bath pool home is ready for you to enjoy. Located on a great boating ...
From $726 per night (USD)VRBO
From $258 per night (USD)VRBO
Cozy 3-bedroom house with AC and WiFi in charming Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your cozy getaway awaits in Cudjoe Key at this phenomenal house. With 3 bedrooms, including 1 queen bed and 2 king beds, ...
From $258 per night (USD)VRBO
From $314 per night (USD)VRBO
Pelican's Roost, Waterfront comfort at Venture Out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
About this space Pelicans Roost is a waterfront home on the Atlantic side of Cudjoe Key with a 17’ dock. Only 20 miles f ...
From $314 per night (USD)VRBO
From $249 per night (USD)Expedia
Cozy Venture Out Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
MANDATORY $125 FEE NOT INCLUDED, PAID TO VENTURE OUT COMMUNITY UPON ARRIVAL. One bedroom home with all that you need. ...
From $249 per night (USD)Expedia
From $355 per night (USD)VRBO
A true waterfront oasis.\nRelax and enjoy your stay with the whole family!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A true waterfront oasis awaits when you stay at this year-round slice of Floridan paradise. This completely renovated Cu ...
From $355 per night (USD)VRBO
From $309 per night (USD)Expedia
Keys cottage, oceanfront, dock, private, great location, fenced backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely ocean front updated lower Keys home in Summerland / Ramrod Key, beautiful open water views, spectacular sunrises, ...
From $309 per night (USD)Expedia
From $684 per night (USD)VRBO
Spanish Queen @Venture Out, Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnish ...
From $684 per night (USD)VRBO
From $216 per night (USD)VRBO
3/2 Home on Canal with Dock and Ocean Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
On canal with ocean access to Atlantic and Gulf sides. 3 bedroom 2 full bath renovated canal front Cudjoe Key beach home ...
From $216 per night (USD)VRBO
From $174 per night (USD)VRBO
Specials for June 2025! Best accommodations for a fabulous Keys Vacation!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SnowScape is a very clean home! A Custom Built design home ready for entertainment with high ceilings and open living ro ...
From $174 per night (USD)VRBO
From $371 per night (USD)Expedia
Waterfront Venture Out Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Mandatory $125 Fee paid to Venture Out Community upon arrival. Waterfront home with concrete seawall for boat dockage. ...
From $371 per night (USD)Expedia
From $714 per night (USD)VRBO
Fisherman's Paradise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Unwind in a brand new, modern and luxurious, waterfront home with great views and a deep water canal in Cudjoe Key Flori ...
From $714 per night (USD)VRBO
From $623 per night (USD)Expedia
Newly renovated cozy and spacious beach house with breathtaking ocean front
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Spectacular ocean front home awaits you in Big Pine Key. Cozy family getaway with breathtaking ocean view and over 450 f ...
From $623 per night (USD)Expedia
From $1030 per night (USD)VRBO
4 Bedroom 3 Bath Water View Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our luxury inspired water front resort community is the perfect Keys vacation get away. We offer a fully furnished 4 bed ...
From $1030 per night (USD)VRBO
From $464 per night (USD)Expedia
Secluded Jungle Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Secluded lower keys oasis on 4 acres. Incredible sunrises and sunsets over the water and jungle. Room for the whole fami ...
From $464 per night (USD)Expedia
From $353 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 $353 per night (USD)VRBO
From $2025 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 $2025 per night (USD)VRBO
From $199 per night (USD)VRBO
Canal Front Paradise! Just a few yards from open water!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to paradise! Want to live like a local? Fish the reefs, snorkel Looe Key, dive for lobster, or kayak where dolph ...
From $199 per night (USD)VRBO
From $140 per night (USD)VRBO
Cudjoe Key, FL RV Resort RV Lot
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
RV lot in Cudjoe Key, FL RV Resort, 35×70, full hook-up. Beautiful community, great relaxing location, close to shopp ...
From $140 per night (USD)VRBO
From $230 per night (USD)VRBO
Ramrod Ocean Retreat –Waterfront Escape (BP#15)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical Long-Term Retreat on Ramrod Key – Boat Dock & Pet Friendly Escape to paradise with this long-term rental (181+ ...
From $230 per night (USD)VRBO
From $228 per night (USD)VRBO
Waterfront Paradise in Florida Keys. Free use of Kayaks, and more!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our 3 bedroom 2 full bath spacious home is on a canal only 3 homes from the open water! We are a Pet Friendly home! You ...
From $228 per night (USD)VRBO
From $428 per night (USD)VRBO
Old Florida Style, wrap around porch, boat basin for dockage, open water
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You will love spending time at this lovely home located on Little Torch Key, with Sunrise view, large property with boa ...
From $428 per night (USD)VRBO
From $381 per night (USD)Expedia
Atlantic Ocean Views - Venture Out 579
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Ocean Views - Venture Out 579 Lovely Stilt 2Bd/2Ba with 35' Dockage This beautiful sparkling clean 2Bd/2Ba stil ...
From $381 per night (USD)Expedia
From $183 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 $183 per night (USD)VRBO
From $345 per night (USD)Expedia
Relaxing Waterfront Escape Near Key West - Venture Out Unit 410
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO410 Relaxing Waterfront Escape Near Key West – 35' Dock, Kayaks and bikes included. Access to beautiful pool and hot t ...
From $345 per night (USD)Expedia
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 $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 $447 per night (USD)VRBO
Mermaid House! Pool, Dockage, Outdoor Bar!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great centr ...
From $447 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 $257 per night (USD)VRBO
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 $257 per night (USD)VRBO
From $562 per night (USD)Expedia
REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience your dream getaway in beautiful Summerland Key within this spacious 4-bedroom retreat. Nestled just a 5-minut ...
From $562 per night (USD)Expedia
From $287 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 $287 per night (USD)Expedia
From $225 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 $225 per night (USD)Expedia
From $409 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 $409 per night (USD)VRBO
From $512 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 $512 per night (USD)Expedia
From $226 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 $226 per night (USD)VRBO
From $358 per night (USD)Expedia
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 $358 per night (USD)Expedia
Click For PricingVRBO
Dickey's Dockside Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Escape to Dickey's Dockside Retreat. This waterfront paradise in the Florida Keys offers a private dock, perfec ...
Click For PricingVRBO
From $594 per night (USD)Expedia
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property that won’t disappoint! Full ...
From $594 per night (USD)Expedia
From $323 per night (USD)VRBO
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forwa ...
From $323 per night (USD)VRBO
Click For PricingExpedia
Waterfront Oceanside 200' Seawall efficiency Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hello ! My name is Debra and I run our account for our family. We love our salty slice of paradise and I look forward t ...
Click For PricingExpedia
From $196 per night (USD)VRBO
L' archipel | Canalfront 2 bedroom retreat on Ramrod Key with brand new dock!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to L’archipel, a charming, newly remodeled monthly rental that offers an ideal retreat for those seeking a relax ...
From $196 per night (USD)VRBO
From $321 per night (USD)Expedia
Ocean/Canal Views 21ft Dock - Venture Out #357
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Ocean/Canal Views 21' Dockage 2Bd/2Ba with Double Porches, Large Landscaped Yard! Island Breeze is a fabulous ...
From $321 per night (USD)Expedia
From $287 per night (USD)VRBO
Florida Keys Water Front Vacation Home with Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3-BR waterfront house with pool that is located directly on an ocean canal with easy access to the Gulf of Mex ...
From $287 per night (USD)VRBO
From $292 per night (USD)Expedia
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House ...
From $292 per night (USD)Expedia
From $161 per night (USD)VRBO
Oceanfront RV Lot with 40' Seawall
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Bring your own RV and experience the majestic beauty of the Florida Keysat this beautiful Oceanfront RV Lot! Lot feature ...
From $161 per night (USD)VRBO
From $240 per night (USD)Expedia
Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
All the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating ...
From $240 per night (USD)Expedia
From $355 per night (USD)VRBO
Peaceful ocean front cottage.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sun ...
From $355 per night (USD)VRBO
From $341 per night (USD)Expedia
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Does your fas ...
From $341 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 $278 per night (USD)Expedia
Beautiful 3 Bedroom Canal Home in Ramrod Key, FL with Open Water Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Cape Cod South! This comfortable home is located 4 lots from the open water on the Gulf side of Ramrod Key. I ...
From $278 per night (USD)Expedia
From $330 per night (USD)VRBO
Lime in the coconut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
You put the "LIME IN THE COCONUT" and add a little fun! Great times to be had in this very nice 3 bedroom 2 bath custom ...
From $330 per night (USD)VRBO
From $325 per night (USD)Expedia
Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has e ...
From $325 per night (USD)Expedia
From $273 per night (USD)VRBO
Big Pine Retreat will leave you wanting to come back year after year!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly remodeled home is cozy, yet spacious. Situated in the Whispering Pines neighborhood you will experience relax ...
From $273 per night (USD)VRBO
From $559 per night (USD)Expedia
LITTLE TORCH TREASURE - 4 Bedroom / 3 Bathroom Canal Front with Pool & Boat Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
“LITTLE TORCH TREASURE'' a proven guest favorite for many years is under new ownership / management in 2023. This RESORT ...
From $559 per night (USD)Expedia
From $342 per night (USD)VRBO
LiL Piece of Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
ALL BOATERS!!! ALL FISHERMAN WELCOME This 3 bedroom, 2 bathroom home has everything you need. Built in 2019 and comfort ...
From $342 per night (USD)VRBO
From $2324 per night (USD)Expedia
Frigate`s Nest: Luxurious 8-Bed/8-Bath Single Family with Open Water Views,
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
Welcome to your exclusive waterfront retreat in the enchanting Little Torch Key, nestled in the heart of the Florida Key ...
From $2324 per night (USD)Expedia
From $397 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 $397 per night (USD)VRBO
From $189 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 $189 per night (USD)Expedia
From $297 per night (USD)VRBO
Relax by Florida Keys Beaches, just a 7-min drive away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
In beautiful Summerland Key, you'll find our lovely two-bedroom getaway that showcases stunning Florida Keys scenery. Si ...
From $297 per night (USD)VRBO
From $210 per night (USD)Expedia
Waterfront Home in The Fabulous Florida Keys with Peak-A-Boo Views of the Bay!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. We’d like to share our home with you. It’s a very ...
From $210 per night (USD)Expedia
From $419 per night (USD)VRBO
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Castaway to Sugarloaf Key for a vacation home like no other. This large corner lot 4 bedroom / 3-bathroom home offers un ...
From $419 per night (USD)VRBO
From $631 per night (USD)VRBO
Open Water ~ Pool Home in Summerland Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Prime Oceanfront Tropical Gem & The Ultimate in Luxury Waterfront Living! Florida Keys luxury deep water oceanfront pool ...
From $631 per night (USD)VRBO
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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 $635 per night (USD)Expedia
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)Expedia
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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 $270 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 $270 per night (USD)Expedia
From $1120 per night (USD)VRBO
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)VRBO
From $206 per night (USD)VRBO
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 $206 per night (USD)VRBO
From $418 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 $418 per night (USD)VRBO
From $542 per night (USD)Expedia
House of the Rising Sun - VO479
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VO479 Spectacular Oceanfront Panoramic Views! 55' Seawall w/ Whips- A Boater's Paradise!Enjoy breathtaking panoramic oce ...
From $542 per night (USD)Expedia
From $823 per night (USD)VRBO
Newly Renovated Ocean Estate- Relax and enjoy this magnifecent
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Magnificent Ocean Front Estate! Enjoy breathtaking views of the ocean from the large screened in porch. Prepare freshly ...
From $823 per night (USD)VRBO
From $299 per night (USD)Expedia
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 $299 per night (USD)Expedia