National Key Deer Refuge Rentals
- From $334 per night (USD)
VRBO
Fisherman's Delight! - Venture Out Unit 410
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO410 Fisherman's Delight! 35' Dockage 2Bd/2Ba with Covered Porch! This sparkling clean and beautiful canalfront home f ...
From $334 per night (USD)VRBO
- From $215 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 $215 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $320 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 $320 per night (USD)Expedia
- From $124 per night (USD)
VRBO
Love Shack | 2 Bed, 1 Bath
- 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 $124 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Dog-friendly, waterfront retreat with a Bohemian vibe, pool, bar, & firepit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key Lime Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $359 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Mermaid House! Pool, Dockage, Outdoor Bar!
- Bedrooms:
- 3
- 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 $385 per night (USD)VRBO
- From $95 per night (USD)
Expedia
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 $95 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Sunshine 23 | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
All the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating ...
From $179 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Sailfish Dream on Cudjoe Key
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This 2'nd floor 2 bedroom/2 bath home is your tropical getaway. The home is at MM 23 giving you Key West or Marathon eq ...
From $200 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $283 per night (USD)
Expedia
Low Key Sunrise: Waterfront pool home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy gorgeous open water views from this 2 bedroom, 2 bathroom pool home on Ramrod Key. Sip your morning coffee while w ...
From $283 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Recently Renovated Home With Deepwater Canal
- 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 $200 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $599 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 $599 per night (USD)VRBO
- From $173 per night (USD)
Expedia
The Pineapple Cottage: Live Your Best Keys Life, 3BR Canal Front Home, Dockage & Pet-Friendly Bliss!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to The Pineapple Cottage, a delightful canal-front home on the serene shores of Big Pine Key. Offering the epitom ...
From $173 per night (USD)Expedia
- From $927 per night (USD)
VRBO
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
- Bedrooms:
- 4
- 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 $927 per night (USD)VRBO
- From $550 per night (USD)
Expedia
REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Impeccably designed and maintained canal front home in Summerland Cove with a Pool! This fully fenced and gated para ...
From $550 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Beautiful Ocean Views 35' Dockage - Venture Out unit 469
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VO469 Beautiful Ocean Views 35' Dockage 2Bd/2Ba This beautiful home on stilts overlooks the open water for breathtakin ...
From $385 per night (USD)VRBO
- From $265 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 $265 per night (USD)Expedia
- 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 #12 - 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 $300 per night (USD)
Expedia
Open Water Views - Venture Out Unit 373
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO373 Ocean Views 35' Dockage Located in the Marina Basin If you are looking for a great location this 2 Bedroom / 2 Bat ...
From $300 per night (USD)Expedia
- From $225 per night (USD)
VRBO
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)VRBO
- From $300 per night (USD)
Expedia
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 $300 per night (USD)Expedia
- From $631 per night (USD)
VRBO
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO093 OCEANFRONT GEM! TRUE SOUTHERN EXPOSURE STILT 2BD/2BA 35' SEAWALL Enjoy breathtaking panoramic ocean views from th ...
From $631 per night (USD)VRBO
- From $189 per night (USD)
Expedia
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PINK COTTAGE UNIT #3 - Sleeps 4 ACCOMODATIONS: UNIT #3 comes with TV, AC, WIFI & Full Kitchen. full kitchen. Enjoy th ...
From $189 per night (USD)Expedia
- Click For Pricing
VRBO
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 $302 per night (USD)
Expedia
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
- 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 $302 per night (USD)Expedia
- From $253 per night (USD)
VRBO
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 $253 per night (USD)VRBO
- Click For Pricing
Expedia
Island Dreams in Paradise! - Venture Out Unit 537
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Island Dreams in Paradise! Lovely Vacation Home with Large Enclosed Porch! This beautiful newly remodeled home is a trop ...
Click For PricingExpedia
- Click For Pricing
Expedia
Ground Level Canal Front Home Lower Keys. Quick Atlantic and Gulf Access.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our fully renovated, ground-floor CBS home, ideally positioned on a canal front. This home offers the conven ...
Click For PricingExpedia
- From $225 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 $225 per night (USD)Expedia
- From $110 per night (USD)
VRBO
FALL SPECIAL!!! NEW RATES<br>🏴☠️ PIRATES PLEASURE 🏴☠️<br>
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Pirates Pleasure is a family owned home in a small neighborhoood community on the bay side of our hidden gem...Little To ...
From $110 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Beautiful House on Ramrod Key with boat slip and easy water access.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The house is very spacious. Large front & back decks. Newer furniture through-out. The house is on a lagoon and you can ...
From $300 per night (USD)VRBO
- From $249 per night (USD)
VRBO
10 minutes away from Bahia Honda and 30 minutes away from Key West
- Bedrooms:
- 2
- 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 $249 per night (USD)VRBO
- From $250 per night (USD)
Expedia
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come vacation in this cozy two bedroom with one bath home. The home has been recently renovated. Just added a non touch ...
From $250 per night (USD)Expedia
- From $158 per night (USD)
VRBO
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 $158 per night (USD)VRBO
- Click For Pricing
Expedia
3\/2 two story home with pool and 80' dock on canal ocean side.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful property and landscaping, 3/2 with pool sleeps 8-10, large 12,000 sq ft lot with 80' dock, The place to be is ...
Click For PricingExpedia
- From $394 per night (USD)
VRBO
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
- Bedrooms:
- 3
- 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 $394 per night (USD)VRBO
- From $234 per night (USD)
Expedia
Canal house with dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
From here you can enjoy all that the Keys have to offer. Conveniently located at the 23 mile marker. Walk to Square G ...
From $234 per night (USD)Expedia
- From $625 per night (USD)
VRBO
Open Water ~ Pool Home in Summerland Key
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Prime Oceanfront Tropical Gem & The Ultimate in Luxury Waterfront Living! Florida Keys luxury deep water oceanfront pool ...
From $625 per night (USD)VRBO
- From $235 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 $235 per night (USD)Expedia
- From $352 per night (USD)
VRBO
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 $352 per night (USD)VRBO
- From $429 per night (USD)
VRBO
Reel Caribbean Getaway | 4 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Fantastic deep-water boating from this spacious, gated, 4 bedroom / 2.5 bath home on Summerland Key's Caribbean Drive Ea ...
From $429 per night (USD)VRBO
- From $518 per night (USD)
VRBO
Ocean Front - Private 56' Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VO095 Spectacular Oceanfront Panoramic Views 56' Seawall Boaters Paradise! $150 additional discount given at booking for ...
From $518 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Searching for your own private Keys resort? Look no further! Our "Retiro Sin Nombre" home is located on the famed and ...
From $399 per night (USD)Expedia
- From $408 per night (USD)
VRBO
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 $408 per night (USD)VRBO
- From $714 per night (USD)
Expedia
Newly Renovated Ocean Estate- Relax and enjoy this magnifecent
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Magnificent Ocean Front Estate! Enjoy breathtaking views of the ocean from the large screened in porch. Prepare freshly ...
From $714 per night (USD)Expedia
- From $185 per night (USD)
VRBO
35 min from Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Very relaxing spot with a large back porch, and perfect for boating with access to the bay or ocean. Just lounge around ...
From $185 per night (USD)VRBO
- From $526 per night (USD)
Expedia
Pirates Cove | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream getaway on Cudjoe Key! This 3-bedroom, 2-bathroom monthly rental offers a slice of paradise with i ...
From $526 per night (USD)Expedia
- From $2118 per night (USD)
VRBO
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 $2118 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Come relax at Sandy Bottom Beach Cottage!!!!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful Summerland Key!! Two houses from the Atlantic Ocean. Enjoy boating, kayaking, swimming in the 28' x 9' swim s ...
From $450 per night (USD)Expedia
- From $225 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 $225 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Casa Sirena, FL Keys Canalfront 3BD\/2BA home offers a small pool & private dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to “Casa Sirena”, a canal-front paradise home nestled in the peaceful lower Florida Keys. Upon entering your ren ...
From $214 per night (USD)Expedia
- From $500 per night (USD)
VRBO
LITTLE TORCH TREASURE - 4 Bedroom \/ 3 Bathroom Canal Front With Pool & LIFT!
- 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 $500 per night (USD)VRBO
- From $317 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 $317 per night (USD)Expedia
- From $130 per night (USD)
VRBO
Barbados Bungalow: Waterfront Paradise, Canalfront, Boat Ramp, Dogs OK, Prime Ramrod Key Corner Lot!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the enchanting Barbados Bungalow, your perfect vacation retreat in the heart of the Florida Keys. This charmin ...
From $130 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Cuddie Cottage: 2BR Waterfront Home in Venture Out Resort, Open Water Views, Shared Pool & Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Cuddie Cottage, your charming haven nestled within the picturesque Venture Out resort on Cudjoe Key. This del ...
From $214 per night (USD)Expedia
- From $305 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 $305 per night (USD)VRBO
- From $246 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 $246 per night (USD)Expedia
- From $265 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 $265 per night (USD)VRBO
- From $274 per night (USD)
Expedia
House, relaxing space,waterfront at Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful house located in Cudjoe Key, one of the most beautiful and relaxing keys in the area with a canal and acc ...
From $274 per night (USD)Expedia
- From $244 per night (USD)
VRBO
Oceanfront home with 2 kayaks, 2 bikes, deck, ocean views, grill, washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Amada Grenada Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $244 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Reel Paradise in the Lower Keys- 200 ft of dockage + heated pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise awaits in the Lower Keys! Situated on a large corner lot, you have over 200 feet of concrete dockage so BIG B ...
From $375 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private 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 $278 per night (USD)VRBO
- From $120 per night (USD)
Expedia
Oceanfront RV Lot with 40' Seawall
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Bring your own RV and experience the majestic beauty of the Florida Keys at this beautiful Oceanfront RV Lot! Lot featur ...
From $120 per night (USD)Expedia
- From $257 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 $257 per night (USD)VRBO
- From $329 per night (USD)
Expedia
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 ...
From $329 per night (USD)Expedia
- From $564 per night (USD)
VRBO
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 $564 per night (USD)VRBO
- From $280 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 $280 per night (USD)VRBO
- Click For Pricing
VRBO
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 PricingVRBO
- From $178 per night (USD)
Expedia
27316 Martinique Ln | 2 Bed, 1 Bath
- Bedrooms:
- 2
- 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 $178 per night (USD)Expedia
- From $305 per night (USD)
VRBO
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 $305 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Blue Lobster Lodge - Venture Out #543
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BLUE LOBSTER LODGE VO 543 Comfortable 2 Bedroom 1.5 Bath Dry Lot This cozy 2 bedroom / 1.5 bath sleeps 6. It's a great p ...
From $225 per night (USD)Expedia
- From $255 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 $255 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
- Bedrooms:
- 3
- 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 $250 per night (USD)Expedia
- From $830 per night (USD)
VRBO
Key West Paradise w\/ Private Pool + Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to the lush, green, beautiful paradise of the Florida Keys at this stunning 4-bedroom, 2-bathroom vacation rental ...
From $830 per night (USD)VRBO
- From $299 per night (USD)
Expedia
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
- 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 $299 per night (USD)Expedia
- From $150 per night (USD)
VRBO
SEA SHELL COTTAGE UNIT #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink and microwave oven. Enjoy the communal outdoor ...
From $150 per night (USD)VRBO
- From $186 per night (USD)
Expedia
Coastal Paradise | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to this charming 2 bedroom, 1 bathroom vacation home nestled on a picturesque Breezeswept Beach Estates canal. T ...
From $186 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Tropical Tides in Cudjoe Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an Oceanfront getaway in this Beautiful home, boasting stunning panoramic ocean views. Featuring 2 bedrooms and 2 ...
From $325 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Amazing house on a deep water canal with easy access to the ocean.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine yourself on your own multi-level structure (feels like your own fort!) with balconies all around and amazing vie ...
From $300 per night (USD)Expedia
- From $382 per night (USD)
VRBO
Hammock Bay! Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique private compound offers 200ft extravagant dock that can hold up to a 50ft vessel and provides safe harbor for any ...
From $382 per night (USD)VRBO
- From $246 per night (USD)
Expedia
Waterfront Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a wonderful relaxing vacation in this Keys-styled open-water home located on the east side of Sugarloaf Key. This ...
From $246 per night (USD)Expedia
- Click For Pricing
Expedia
Lower Keys Canal Front Bungalow on Little Torch Key. Pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly renovated canal front attached bungalow is a wonderful place to get away in the Florida Keys on a budget. Con ...
Click For PricingExpedia
- From $217 per night (USD)
Expedia
Privateer`s Prize | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect waterfront retreat on Cudjoe Key! This pet-friendly 3 bed/2 bath monthly rental is situated on a ...
From $217 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Very Private 3 Bedroom \/ 2 Bath Canal Home in Little Torch Key w\/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Paradise Blue....a true slice of paradise on Little Torch Key! This private retreat sits on 2 lots with the h ...
From $350 per night (USD)VRBO
- From $395 per night (USD)
Expedia
PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location Location Location! Welcome to our very special community Summerland Key. Summerland is one of the best fishi ...
From $395 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Paradise in the Fabulous Florida Keys - Fishing and Dive capital of the world.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful open water views with gorgeous Sunsets across Cudjoe Bay. Enjoy happy hour overlooking the canal and dock or o ...
From $233 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Relax in Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very eclectic Conch-style Key West home on Big Pine Key. Appropriately appointed for a relaxing stay. Large living room ...
From $180 per night (USD)Expedia
- From $153 per night (USD)
VRBO
Boat Dock \/ Private Airstrip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your Canal Front Oasis on Summerland Key! Dock your boat along the sea wall, offering convenient access to wo ...
From $153 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Waterfront home with boat\/canal access, screened lanai, & renovated interior
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Endless Summerland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $254 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Gorgeous New 4\/3 With Heated Pool\/Spa And Large Deep Water Boat Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is a beautiful newly built 4 bedroom, 3 bathroom house located on a cul-de-sac in quiet Cudjoe Gardens. The house ...
From $318 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Canal front keys home 3bedroom, 2 bath.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Like new pool home, built in 2020. 3 bedroom, 2 bath home, canal front property. Private 37’ dock with fish cleaning ...
From $240 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Loggerhead Lagoon | Canalfront, Tiki Hut & Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Loggerhead Lagoon is a stunning, tropically themed, 3-bed 2-bath home located on a large private lot that offer ...
From $195 per night (USD)VRBO
- From $348 per night (USD)
Expedia
Paradise Escape! - VO466 35' Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VO466 Paradise Escape! Perfect Location 35' Dockage! It's a wonderful time to enjoy Paradise! Enjoy endless expansive w ...
From $348 per night (USD)Expedia
- Click For Pricing
Expedia
Retiro Sin Nombre
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Searching for your own private Keys resort? Look no further! Our "Retiro Sin Nombre" home is located on the famed and ...
Click For PricingExpedia
- From $180 per night (USD)
VRBO
3 Bedroom 2 Bath Canal front home with Great Boating
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are looking for a light, bright, and tropical rental home this is it!! This 3 bedroom 2 bath home is beautifully ...
From $180 per night (USD)VRBO
- From $446 per night (USD)
VRBO
Casa Cielo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your private get away in this canal home with ocean views. It's a quick trip to deep water and endless boatin ...
From $446 per night (USD)VRBO
- From $319 per night (USD)
VRBO
Pelican's Paradise - Unit 507 Venture Out 1 Bedroom\/1 Bath Canal Front Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to Pelican's Paradise, a charming one-bedroom, one-bath cottage nestled in the private, gated community of Ventur ...
From $319 per night (USD)VRBO