National Key Deer Refuge Rentals
From $526 per night (USD)VRBO
Luxurious Oceanfront Home on Beach, Dock, Heat\/Cool Pool, Kayaks, Bikes, Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This luxurious Cudjoe Key vacation rental home, located directly on a sandy beach overlooking the crystalline Atlantic O ...
From $526 per night (USD)VRBO
From $646 per night (USD)Expedia
Tropical Paradise - Ocean front with swim spa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and roman ...
From $646 per night (USD)Expedia
From $387 per night (USD)VRBO
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 $387 per night (USD)VRBO
From $208 per night (USD)Expedia
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 $208 per night (USD)Expedia
From $309 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 $309 per night (USD)VRBO
From $844 per night (USD)Expedia
Summerland Nest - Ocean view with private beach and pool
- Bedrooms:
- 5
- 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 $844 per night (USD)Expedia
From $495 per night (USD)VRBO
2 Bedroom 2.5 Bath Luxury Townhome 26 Miles from Downtown Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Little Torch Cottages offers the perfect Keys location, fully appointed luxury 2 bedroom 2.5 bath townhome with breath t ...
From $495 per night (USD)VRBO
From $670 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 $670 per night (USD)Expedia
From $1115 per night (USD)VRBO
Luxurious, Private, Oceanfront, Gated Home
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Stunning 1 acre oceanfront gated estate with lush landscaping, beach and extreme privacy due to the adjacent wildlife re ...
From $1115 per night (USD)VRBO
From $197 per night (USD)Expedia
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 $197 per night (USD)Expedia
From $2166 per night (USD)VRBO
CASA AQUA - 16 Acre Open Water Spanish Style Casual Elegance
- Bedrooms:
- 4
- 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 $2166 per night (USD)VRBO
From $621 per night (USD)Expedia
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)Expedia
From $349 per night (USD)VRBO
Summerland Key Oceanfront
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our longtime winter tenant who has rented our house from November through April for the last 7 years has bought his own ...
From $349 per night (USD)VRBO
From $135 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 $135 per night (USD)Expedia
From $357 per night (USD)VRBO
Canal Front Home Showcasing Stellar Sunsets with Ocean Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the White Heron! Bring your binoculars and boat.....this lovely 3 bedroom home faces Pine Channel and also ov ...
From $357 per night (USD)VRBO
From $240 per night (USD)Expedia
Casa Blanca | Gorgeous ground-level 2 bed\/2 bath home on Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to your own piece of paradise with this beautifully modern ground-level vacation rental nestled in a tranquil nei ...
From $240 per night (USD)Expedia
Click For PricingVRBO
Dog-friendly, waterfront retreat with a Bohemian vibe, pool, bar, & firepit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Key Lime Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
Click For PricingVRBO
From $308 per night (USD)Expedia
Waterfront, Bayview home with dockage sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Multiple month rentals welcomed and encouraged. Amazing upstairs 2 bedroom, 1 bathroom, downstairs 1 bedroom 1 bathroo ...
From $308 per night (USD)Expedia
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 $525 per night (USD)Expedia
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 $525 per night (USD)Expedia
From $424 per night (USD)VRBO
Atlantic Ocean Views - Venture Out 579
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Ocean Views - Venture Out 579 Lovely Stilt 2Bd/2Ba with 35' Dockage This beautiful sparkling clean 2Bd/2Ba stil ...
From $424 per night (USD)VRBO
From $175 per night (USD)Expedia
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 $175 per night (USD)Expedia
From $430 per night (USD)VRBO
Fisherman's Delight! - Venture Out Unit 410
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VO410 Fisherman's Delight! 35' Dockage 2Bd/2Ba with Covered Porch! This sparkling clean and beautiful canalfront home f ...
From $430 per night (USD)VRBO
From $212 per night (USD)Expedia
Canal Front Home to Dock and lift your boat in Lower Keys Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This comfortable elegant 3B/3B stilt home offers paradise in the Lower Keys. CAN BE RENTED AS A 4B/4B DETAILS BELOW. ...
From $212 per night (USD)Expedia
From $210 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 $210 per night (USD)VRBO
From $401 per night (USD)Expedia
Keys Time #437 - Cudjoe Key, Oceanfront Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Keys Time!! Slow it down. Unwind. Enjoy the Island Life! This Beautifully furnished 2 bedroom 2 bath canal f ...
From $401 per night (USD)Expedia
From $188 per night (USD)VRBO
Amazing Paradise House Canal Front with access to Atlantic and Gulf.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
BEAUTIFUL KEY PROPERTY !!!!SEASONAL Monthly Rental only, built in 1990, Big Pine Fishing house is a 2 BR, 2 BA, with a l ...
From $188 per night (USD)VRBO
From $173 per night (USD)Expedia
Ramrod Seaside Retreat- BP#15
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This long term (181 days plus )is tucked away in a tropical paradise at Ramrod Key. This is one of the most unique place ...
From $173 per night (USD)Expedia
From $332 per night (USD)VRBO
The Orchid House, 5 bed\/2bath Canal Front Home, Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to The Orchid House, your perfect getaway on Ramrod Key! This spacious five-bedroom, two-bathroom canal-front ho ...
From $332 per night (USD)VRBO
From $355 per night (USD)Expedia
Peaceful ocean front cottage.
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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)Expedia
From $339 per night (USD)VRBO
Waterfront Oasis in the Keys
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront oasis with meticulous finishes and a vibrant modern interior giving you the feeling of an upscale resort. Fro ...
From $339 per night (USD)VRBO
From $247 per night (USD)Expedia
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $247 per night (USD)Expedia
From $332 per night (USD)VRBO
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
- Bedrooms:
- 3
- 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 $332 per night (USD)VRBO
From $351 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 $351 per night (USD)Expedia
From $465 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 $465 per night (USD)VRBO
From $216 per night (USD)Expedia
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)Expedia
From $257 per night (USD)VRBO
PALM COTTAGE \nSummer vacation Lobster and Fishing season!\nsleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $257 per night (USD)VRBO
From $338 per night (USD)Expedia
Waterfront vacation home in Big Pine Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 1
Welcome to Casa Guava. Enjoy this water front home in Eden Pines. Only 29 miles to Key west. Bring your boat, deep water ...
From $338 per night (USD)Expedia
From $433 per night (USD)VRBO
Mad Mahi Canal with pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atl ...
From $433 per night (USD)VRBO
From $298 per night (USD)Expedia
Beautiful waterfront home with central AC, dock, lovely balcony & patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Big Pine Key Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $298 per night (USD)Expedia
From $138 per night (USD)VRBO
Relaxing Florida Keys canal front home in nature preserve
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Kokomo Palms! This relaxing getaway is a single family, canal front home located on Big Pine Key. It offers ...
From $138 per night (USD)VRBO
From $184 per night (USD)Expedia
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 $184 per night (USD)Expedia
From $360 per night (USD)VRBO
Ocean View Splendor on Summerland Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the beautiful waterfront elevated home in the Florida Keys overlooking the Atlantic Ocean. Relax in the screened ...
From $360 per night (USD)VRBO
From $159 per night (USD)Expedia
Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wa ...
From $159 per night (USD)Expedia
From $1030 per night (USD)VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $1030 per night (USD)VRBO
From $726 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 $726 per night (USD)Expedia
From $222 per night (USD)VRBO
Tarpon Canal | Nearly new 3 bed\/2 bath home with canal views on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nicely appointed and nearly new, this 3 bedroom/2 bathroom home sits on a clear swimming canal on the gulfside of Ramrod ...
From $222 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 $366 per night (USD)Expedia
Sun Bake @ Sponge Cake, 64' Sea Wall,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Canal front home in a gated community. Large screened in porch. Sleeps 4 comfortably + a queen sleeper sofa if needed. ...
From $366 per night (USD)Expedia
From $285 per night (USD)VRBO
Fishing, swimming and relaxing on the porch in Big Pine Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. Its located in Tropical Estates, a quiet u ...
From $285 per night (USD)VRBO
From $1074 per night (USD)Expedia
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 $1074 per night (USD)Expedia
From $201 per night (USD)VRBO
Reel Paradise | Fabulous sunsets from this canalfront 2 bed\/2 bath on Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy 2 bed/2 bath canalfront monthly rental nestled in the natural beauty of the Big Pine Key. Located in the quiet Eden ...
From $201 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 $568 per night (USD)VRBO
Emerald Seas - Florida Keys Ocean Front Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...
From $568 per night (USD)VRBO
Click For PricingExpedia
Tropical paradise on open water 35 ft seawall in beautiful Venture Out Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ocean Front 35’ Seawall – Spectacular views from this 2 Bedroom 2 Bathroom ocean front stilt home! This home features a ...
Click For PricingExpedia
From $162 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 $162 per night (USD)VRBO
From $468 per night (USD)Expedia
Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $468 per night (USD)Expedia
From $238 per night (USD)VRBO
Waterfront Pool Home! - Heavenly Hideout - Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Heavenly Hideout - Your Waterfront Pool Home - Escape to the Florida Keys!! Escape to paradise in this beautiful vacati ...
From $238 per night (USD)VRBO
From $137 per night (USD)Expedia
RV Lot 621 Venture Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Experience the tranquility of this freshly landscaped RV lot nestled within Venture Out. This spacious 35' by 70' lot fe ...
From $137 per night (USD)Expedia
From $632 per night (USD)VRBO
Beach Haven: Modern 4-Bed\/2-Bath Single Family Home with Breathtaking Open Water
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Introducing Beach Haven, an exquisite and contemporary 4-bedroom, 2-bathroom single-family residence nestled on the pict ...
From $632 per night (USD)VRBO
Click For PricingExpedia
The Happy House will be your Happy Place
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This house has a seawall where you can dock your boat in a deep canal. It over looks a protected preserve where you can ...
Click For PricingExpedia
From $803 per night (USD)VRBO
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 $803 per night (USD)VRBO
From $435 per night (USD)Expedia
Endless Water Views - Venture Out 526
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Endless Water Views - Venture Out 526 Newer Stilted 2Bd/2Ba Home with WIFI 35' Dockage Open Water Views! This newer cons ...
From $435 per night (USD)Expedia
From $253 per night (USD)VRBO
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 $253 per night (USD)VRBO
From $440 per night (USD)Expedia
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Shangri-la in the Keys! Enjoy the water views and a 45' dock space! VO unit 413 - 2Bd/2Ba Stilt Home Newly renovated s ...
From $440 per night (USD)Expedia
From $331 per night (USD)VRBO
Treasure Isle at Parks End - Venture Out 062
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Treasure Isle at Parks End - Venture Out 062 Southern Location Walk to Ocean! This sparkling clean and bright 2 Bedroom ...
From $331 per night (USD)VRBO
From $379 per night (USD)Expedia
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 $379 per night (USD)Expedia
From $314 per night (USD)VRBO
Pelican's Roost, Waterfront comfort at Venture Out
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $244 per night (USD)Expedia
Yellowstone by the Sea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Here is a unique and tranquil getaway that is the best of all worlds. Enjoy setting in the soft tropical breezes that ov ...
From $244 per night (USD)Expedia
Click For PricingVRBO
Fill the Day with Sun & Fun!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Do everything or nothing at this Florida Keys 2br/2ba! Relax on the screened porch, kayak in the canals or take a boat r ...
Click For PricingVRBO
From $413 per night (USD)Expedia
Florida Keys Paradise!
- Bedrooms:
- 4
- 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 $413 per night (USD)Expedia
From $309 per night (USD)VRBO
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 $309 per night (USD)VRBO
From $690 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 $690 per night (USD)Expedia
From $288 per night (USD)VRBO
Nature's Paradise - Inground Pool - GREAT MONTHLY RENTAL RATE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Contemporary home with cathedral ceilings on corner canal, featuring a 40-foot boat dock with powered davits and 31 foot ...
From $288 per night (USD)VRBO
From $323 per night (USD)Expedia
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)Expedia
From $226 per night (USD)VRBO
L' archipel | Canalfront 2 bedroom retreat on Ramrod Key with brand new dock!
- 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 $226 per night (USD)VRBO
From $368 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 $368 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:
- 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 $292 per night (USD)Expedia
From $215 per night (USD)VRBO
Escape the Ordinary and Experience Island Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Tarpon Retreat is a luxurious vacation rental home, nestled in an island paradise located in the Big Pine Key Deer Refug ...
From $215 per night (USD)VRBO
From $257 per night (USD)Expedia
Stylish & Modern Summerland Key Private Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the very best of the Florida Keys from the comfort & convenience of this upgraded waterfront retreat! Perfectly ...
From $257 per night (USD)Expedia
From $111 per night (USD)VRBO
Waterfront RV Lot w 35' dock in \"Venture Out\". Utility hookups & beautiful views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
35' dock on a canal in Venture Out! This is a RV lot only, there is no house. Simply drive up with your travel trailer/R ...
From $111 per night (USD)VRBO
From $422 per night (USD)Expedia
Tropical Canal-front Cottage in the Lower Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Snapper Villa is the perfect destination for those looking for a tropical getaway. Set on a canal-front in the Big Pine ...
From $422 per night (USD)Expedia
From $139 per night (USD)VRBO
20 ft from your room to a clean canal full of fish and lobsters and crabs.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Only 10 minutes to bahia honda beach, rated top ten every year. 35 min to key west. 3 hrs to miami, a great sight seeing ...
From $139 per night (USD)VRBO
From $371 per night (USD)Expedia
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 $371 per night (USD)Expedia
From $201 per night (USD)VRBO
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 $201 per night (USD)VRBO
From $229 per night (USD)Expedia
FLAMINGO COTTAGE - Summer vacation\nLobster and Fishing season- sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Flamingo Cottage is a studio unit that includes a Queen-sized bed in the bedroom area, a full kitchen, bathroom with ...
From $229 per night (USD)Expedia
From $235 per night (USD)VRBO
Summerland Cottage- Our Little Piece of Paradise with an Old School Key Vibe!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** Phone Meeting Required before booking approval!! Host Missy Proctor (561) 667-0160 *** Don't forget to check the VR ...
From $235 per night (USD)VRBO
From $2676 per night (USD)Expedia
Frigate`s Nest: Luxurious 8-Bed\/8-Bath Single Family with Open Water Views,
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 16
Welcome to your exclusive waterfront retreat in the enchanting Little Torch Key, nestled in the heart of the Florida Key ...
From $2676 per night (USD)Expedia
From $520 per night (USD)VRBO
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 $520 per night (USD)VRBO
From $494 per night (USD)Expedia
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 $494 per night (USD)Expedia
From $249 per night (USD)VRBO
Big Pine Waterfront Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming canal-front bungalow in the Florida Keys! This delightful rental offers an unforgettable experie ...
From $249 per night (USD)VRBO
From $223 per night (USD)Expedia
Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfect fishing and boating location on Kemp Channel between Cudjoe Key and Summerland Key. New Pool Installed August ...
From $223 per night (USD)Expedia
From $321 per night (USD)VRBO
FISHERMANS DREAM HOUSE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bring your boats to this amazing house with 180ft. of seawall secluded on a corner lot. Boat ramp minutes away. Ice make ...
From $321 per night (USD)VRBO
From $666 per night (USD)Expedia
Beach Bliss, Oceanfront with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. T ...
From $666 per night (USD)Expedia
From $904 per night (USD)VRBO
Waterfront Captain House with Boat Basin & Ramp!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin for your boat. The property ...
From $904 per night (USD)VRBO
From $164 per night (USD)Expedia
Lower Keys Home getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 30
This lovely 2 bedroom is close to many popular restaurants and is only 35 min from key west. Very close to several boat ...
From $164 per night (USD)Expedia
From $318 per night (USD)VRBO
Cozy Corner 2A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This family friendly neighbor is peaceful and relaxing, very close to many restaurants and also 35 min from key west. Th ...
From $318 per night (USD)VRBO
From $407 per night (USD)Expedia
Enjoy sunrises at this cozy canal front home !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
GRAND SLAM 1952 Coral Way, Big Pine Key Welcome to the Grand Slam! This Unique rental will make y ...
From $407 per night (USD)Expedia