National Key Deer Refuge Rentals
From $243 per night (USD)VRBO
Beautiful Lagoon view on canal pool home Summerland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Home has to be rented for 28 days or longer. Home has high vaulted ceiling and 30 feet of sliding glass windows which ...
From $243 per night (USD)VRBO
From $349 per night (USD)Expedia
Quaint cottage, pool, dockage just minutes to Key West!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #5 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. One of our most spacious ...
From $349 per night (USD)Expedia
From $250 per night (USD)VRBO
A slice of paradise
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Wanna go on vacation but feel Cozy as if your home? We got the place for you! 2 bedroom,1 bathroom with living room,di ...
From $250 per night (USD)VRBO
From $262 per night (USD)Expedia
Cottage with swimming pool and dockage, just minutes to Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cottage #3 - Quaint, clean, comfortable cottage just 20 miles from Key West. Located on the oceanfront. Cottage offers a ...
From $262 per night (USD)Expedia
From $291 per night (USD)VRBO
Nader's Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
From $291 per night (USD)VRBO
From $284 per night (USD)Expedia
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $284 per night (USD)Expedia
From $818 per night (USD)VRBO
Direct Ocean View! 5 Bed\/3 Bath with room for everyone. Large pool and Dock!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. T ...
From $818 per night (USD)VRBO
From $209 per night (USD)Expedia
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cottage #1 - Quaint, clean, comfortable cottage just 20 miles from Key West. Located on the oceanfront. Cottage offers a ...
From $209 per night (USD)Expedia
From $248 per night (USD)VRBO
Vacation like a local
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $248 per night (USD)VRBO
From $631 per night (USD)Expedia
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 $631 per night (USD)Expedia
From $368 per night (USD)VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $368 per night (USD)VRBO
From $223 per night (USD)Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $223 per night (USD)Expedia
From $225 per night (USD)VRBO
Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $225 per night (USD)VRBO
From $737 per night (USD)Expedia
Fandango - private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This house includes all the elements you need for an amazing vacation. Outside the house there are kayaks for adventures ...
From $737 per night (USD)Expedia
From $252 per night (USD)VRBO
Canal Front Home With Pool And Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Terrific tropical getaway for rent!! 2 Bedroom 3 full bath canal front home with large in ground pool, hot tub and 60 f ...
From $252 per night (USD)VRBO
From $661 per night (USD)Expedia
Blue Vacation Home Free Cancellation See Details
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Vacation home has a view over Cudjoe Bay to the Atlantic from the common deck and from the private pool deck. 4 bedroom ...
From $661 per night (USD)Expedia
From $754 per night (USD)VRBO
White Vacation Home Free Cancellation See Details
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Kayaks come with the rental. Small floating dock for your boat. We have 2 other vacation homes right next to this home i ...
From $754 per night (USD)VRBO
From $507 per night (USD)Expedia
Yellow Home FREE PONTOON RENTAL! See details
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you book your stay for the days shown below May 10th - May 23rd, 2025 May 26th - June 7th, 2025 July 5th - July 26th ...
From $507 per night (USD)Expedia
From $499 per night (USD)VRBO
Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' seawal ...
From $499 per night (USD)VRBO
From $1184 per night (USD)Expedia
Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set ...
From $1184 per night (USD)Expedia
From $478 per night (USD)VRBO
Bay View 2 Bed \/ 2.5 Bath Vacation Townhome Rental in Key West Area
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Little Torch Cottages is the perfect Keys vacation get away. Our luxury inspired 2 bedroom townhomes with bay / ocean vi ...
From $478 per night (USD)VRBO
From $208 per night (USD)Expedia
Direct Oceanfront Cottage-Sunrise View- #2,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer and public ramp just arou ...
From $208 per night (USD)Expedia
From $336 per night (USD)VRBO
Sirena Key Cottage in Venture Out
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $336 per night (USD)VRBO
From $176 per night (USD)Expedia
Relaxation in Paradise - Open Water Canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Relaxing in the beautiful Florida Keys, it does not get any better than this! Swimming and snorkeling in the crystal cl ...
From $176 per night (USD)Expedia
From $104 per night (USD)VRBO
Peaceful Island Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This studio bedroom has a private entrance with rustic island feel. It is sufficient for ONE person, only. Queen- size b ...
From $104 per night (USD)VRBO
From $513 per night (USD)Expedia
Kelly's Kabin - Adorable Private Summerland Key Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $513 per night (USD)Expedia
Click For PricingVRBO
Cozy 2 Bedroom home in Summerland Key
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is located in a quiet and cozy area 5 minutes away from the famous Ramrod Swim Hole; a local treasure. It is al ...
Click For PricingVRBO
From $180 per night (USD)Expedia
Waterfront Big Pine Key Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
House, 2 Bedrooms + Sofa bed, 2 Baths, (Sleeps 4-6) Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the ...
From $180 per night (USD)Expedia
From $235 per night (USD)VRBO
Cudjoe Bay Getaway In Paradise
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $235 per night (USD)VRBO
From $193 per night (USD)Expedia
Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the chann ...
From $193 per night (USD)Expedia
From $237 per night (USD)VRBO
Casa Playa | 4 bed\/2 bath canalfront getaway on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Playa, your spacious 4-bedroom, 2-bathroom retreat nestled in the serene beauty of Ramrod Key. This invi ...
From $237 per night (USD)VRBO
From $358 per night (USD)Expedia
Lower Keys Retreat.....
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful home located in Eden Pines subdivision on Big Pine Key has the best of everything. Furnished with the fin ...
From $358 per night (USD)Expedia
From $216 per night (USD)VRBO
Paradise Retreat ~ BPK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
~3/2 home with heated pool located on large ,private and fenced property. Screened room and patio deck. Privacy is key t ...
From $216 per night (USD)VRBO
From $328 per night (USD)Expedia
Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $328 per night (USD)Expedia
From $265 per night (USD)VRBO
Canal Front Home in Big Pine Key with Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedrooms, 2 Baths, Sleeps 6 The 3 bedroom 2 bath canal front home is located in a quiet neighborhood located on Big P ...
From $265 per night (USD)VRBO
From $229 per night (USD)Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #13 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. SpaciouQuaint, clean, co ...
From $229 per night (USD)Expedia
From $169 per night (USD)VRBO
Cottage with Pool and Boat Dockage just minutes to Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cottage #2 - Charming and serene, clean, comfortable cottage just 20 miles from Key West. Located adjacent to the pool. ...
From $169 per night (USD)VRBO
From $439 per night (USD)Expedia
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 $439 per night (USD)Expedia
From $287 per night (USD)VRBO
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. ...
From $287 per night (USD)VRBO
From $160 per night (USD)Expedia
Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy, clean, canal front home is located in a quiet, family friendly, National Key Deer Refuge. 3 bedroom, 2 baths ...
From $160 per night (USD)Expedia
From $338 per night (USD)VRBO
Cudjoe Cottages, swimming pool, just 20 miles from Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
House B - This lovely 3 bedroom 2 full bath home is located on the Atlantic Ocean. There is always a gentle breeze on th ...
From $338 per night (USD)VRBO
From $254 per night (USD)Expedia
Waterfront Relaxation and Barefoot Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Pack your bags and bring your boat! This home is located on the canal with easy access to the Gulf and Atlantic. It is e ...
From $254 per night (USD)Expedia
Click For PricingVRBO
Pirates Pleasure Fishing and Snorkeling.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Mobile home on boating canal, access to the contents for flats fishing and the Atlantic for deep sea fishing. Property ...
Click For PricingVRBO
From $346 per night (USD)Expedia
Springs Venture Out Dolphin House (#386) with beautiful open water views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Home has some of the absolute best views of the Ocean; sitting on your deck watching nature at its best. Our 35ft s ...
From $346 per night (USD)Expedia
From $180 per night (USD)VRBO
Waterfront Big Pine Key Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
House, 2 Bedrooms + Sofa bed, 2 Baths, (Sleeps 4-6) Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the ...
From $180 per night (USD)VRBO
From $256 per night (USD)Expedia
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Minimum Rental is 28 Days to a single family or party (no subleases allowed). Simply Breathtaking VIEWS of the sunset ...
From $256 per night (USD)Expedia
From $357 per night (USD)VRBO
Relaxing 2\/2 Get Away in the Lower Keys!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recently renovated hom ...
From $357 per night (USD)VRBO
From $846 per night (USD)Expedia
6 Bedroom 4 bath<br>Rental Rates are based on the number of guests
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
6 Bedroom 4 bath Rental Rates are based on the number of guests. Base rate is for 6 guests. There is an additional cha ...
From $846 per night (USD)Expedia
From $154 per night (USD)VRBO
2\/2 Canal Front Home Big Pine Key. Easy ocean and gulf access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Terrific Key getaway for rent!! Newly remodeled 2 Bedroom 2 full bath canal front home with 50 feet of dock. Located in ...
From $154 per night (USD)VRBO
From $366 per night (USD)Expedia
Big Pine Key, 3 BR, 2 1\/2 Bath, Private Canal, Close to everything, KW
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** Florida Keys, Big Pine Key, located in Big Pine Key Florid ...
From $366 per night (USD)Expedia
From $177 per night (USD)VRBO
Snowscape is Clean & Tropical Custom Built Home SuperHost
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick acc ...
From $177 per night (USD)VRBO
From $363 per night (USD)Expedia
Views Views! Direct Oceanfront, Beautiful Inside!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless d ...
From $363 per night (USD)Expedia
From $233 per night (USD)VRBO
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $233 per night (USD)VRBO
From $720 per night (USD)Expedia
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with ice maker, 50" TV, refridgerator, fire p ...
From $720 per night (USD)Expedia
From $332 per night (USD)VRBO
Group Therapy | 3 bed, 2 bath home w\/ new pool, quick ocean access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream escape! This beautifully remodeled 3-bedroom, 2-bathroom pool home on Cudjoe Key's oceanside is th ...
From $332 per night (USD)VRBO
From $1316 per night (USD)Expedia
One of the very few beach houses with a daily, rental license in the Keys.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a newly remodeled four bedrooms elegant house. The property located in the heart of Summerland Key. It is the ...
From $1316 per night (USD)Expedia
From $157 per night (USD)VRBO
EMPTY RV LOT - Sea Esta in Cudjoe Key!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This RV LOT has it all!This is a great spot for those who want to enjoy open water views without having the hassle of ge ...
From $157 per night (USD)VRBO
From $237 per night (USD)Expedia
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $237 per night (USD)Expedia
From $316 per night (USD)VRBO
Island Therapy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $316 per night (USD)VRBO
From $516 per night (USD)Expedia
Family friendly canal home,150 ft dock, easy access to Atl & Gulf
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxin ...
From $516 per night (USD)Expedia
From $454 per night (USD)VRBO
NEPTUNES END - 4 Bedrooms \/ 3 Bathrooms Waterfront Retreat- Pool & Sunset Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Neptune’s End is the perfect island getaway home. This home sits ocean front and has unobstructed views of Cudjoe Bay ou ...
From $454 per night (USD)VRBO
From $485 per night (USD)Expedia
Luxury Ocean View 2 Bed \/ 2.5 Bath Townhome in the Keys
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Little Torch Cottages is the perfect vacation get away in the Key West Area. Our luxury inspired 2 bedroom townhomes off ...
From $485 per night (USD)Expedia
From $329 per night (USD)VRBO
Canal Front (Deep Water) Tropical Villa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...
From $329 per night (USD)VRBO
From $344 per night (USD)Expedia
FREE KAYAKS & BIKES! Private Pool Home. Little Torch Key. Great Fishing Area.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
One of the Keys' best-kept secrets is Little Torch Key. Little Torch Key is a tiny island that you'll cross at the 28th ...
From $344 per night (USD)Expedia
From $320 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 $320 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 $149 per night (USD)VRBO
Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The property has direct access to the Atlantic Ocean or the Gulf in minutes, providing some of the finest bluewater fish ...
From $149 per night (USD)VRBO
From $245 per night (USD)Expedia
Enjoy Caribbean weather in the USA. Openings in May 2025!! Book now!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is a bungalow with cathedral ceilings. It is spacious and sparkling clean. Our home is #655 at Venture Out on ...
From $245 per night (USD)Expedia
From $586 per night (USD)VRBO
Mariners Cove - The Kraken House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet C ...
From $586 per night (USD)VRBO
From $205 per night (USD)Expedia
Conch House on a Quiet Canal : Monthly Only
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical ...
From $205 per night (USD)Expedia
From $230 per night (USD)VRBO
SPCL FALL RATES __THREE LOTS WITH POOL AND DOCK!! SECLUDED LOWER KEYS RETREAT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please note that we have a 28 day minimum rental period with no subletting. This is a Monroe County Regulation to preser ...
From $230 per night (USD)VRBO
From $339 per night (USD)Expedia
Open water views, New heated & chilled pool. Huge master suite! wraparound decks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $339 per night (USD)Expedia
From $132 per night (USD)VRBO
Keys Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 1
Very relaxing 3 bedroomwith a large back porch, and perfect for boating with access to the bay or ocean. Just lounge aro ...
From $132 per night (USD)VRBO
From $493 per night (USD)Expedia
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy memorable sunsets, magnificent bay / ocean views and revel in all the local charm and activities the Keys have to ...
From $493 per night (USD)Expedia
From $964 per night (USD)VRBO
Connecting 2 Bed \/ 2.5 Bath Luxry Townhomes w\/Seperate Entrances - Can Sleep 12
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Our luxury inspired water front resort community is the perfect Keys vacation get away. We offer connecting fully furnis ...
From $964 per night (USD)VRBO
From $233 per night (USD)Expedia
Relax at the flying hogfish
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West an ...
From $233 per night (USD)Expedia
From $176 per night (USD)VRBO
The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $176 per night (USD)VRBO
From $261 per night (USD)Expedia
Beautiful Canal Front Heated Pool 4 Bdr Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Modern 3 bedroom 2 bath stilt home centrally located in Big Pine. Large heated / chilled swimming pool with tanning le ...
From $261 per night (USD)Expedia
From $910 per night (USD)VRBO
Waterfront Anchor House with Boat Basin & Ramp!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The ...
From $910 per night (USD)VRBO
From $598 per night (USD)Expedia
Waterfront Haven House with Boat Basin & Ramp!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The ...
From $598 per night (USD)Expedia
From $286 per night (USD)VRBO
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $286 per night (USD)VRBO
From $536 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 $536 per night (USD)Expedia
From $403 per night (USD)VRBO
Mickey and Lynn's House of Windows
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Secluded two story above garage corner lot gives you a panoramic views of water and near by park. Key deer frequent the ...
From $403 per night (USD)VRBO
From $396 per night (USD)Expedia
**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $396 per night (USD)Expedia
From $751 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 $751 per night (USD)VRBO
From $823 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 $823 per night (USD)Expedia
From $563 per night (USD)VRBO
Great Location , Great Vibes, Great Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Quiet, secluded Keys house with a pool. Ideal for larger groups of friends and family's. Equal distance to Marathon an ...
From $563 per night (USD)VRBO
From $412 per night (USD)Expedia
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community bui ...
From $412 per night (USD)Expedia
From $799 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 $799 per night (USD)VRBO
From $350 per night (USD)Expedia
Florida keys Waterfront,Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $350 per night (USD)Expedia
Click For PricingVRBO
Affordable, Adorable home waiting for you in Cudjoe Key
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Adorable canal front 2 bed/2 bath home for rent in Cudjoe Key. This indoor/outdoor floor plan is complemented by 3 twelv ...
Click For PricingVRBO
From $469 per night (USD)Expedia
Oceanfront Sunsets in the Florida Keys
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FOLSOM'S FOLLY... Summerland Key, Florida Interesting architecture with breezy views of the water. All rooms beautiful ...
From $469 per night (USD)Expedia
From $472 per night (USD)VRBO
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This Private Canal front Pool/TIKI home with Dock, sits in Port Pine Heights BIG PINE KEY FL. See key deer every day wa ...
From $472 per night (USD)VRBO
From $178 per night (USD)Expedia
Bungalow oasis with lots of room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fenced property! Not to mention all the key deer that come and visit. 2 bedrooms 1.5 bathroom 1 car garage concrete ho ...
From $178 per night (USD)Expedia
From $462 per night (USD)VRBO
SEA EVERYWHERE! Open Water & 2 Boat Basins!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Beautiful open-water views of the Bahia Honda bridge from nearly every room! Key deer grazing daily in your yard. Tw ...
From $462 per night (USD)VRBO
From $279 per night (USD)Expedia
Paradise in the lower KEYS!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Master bedroom has a KING bed, second bedroom has a KING bed, third bedroom has a Queen and a full bed that sleep 3, ho ...
From $279 per night (USD)Expedia
From $575 per night (USD)VRBO
SEA FOREVER! Gorgeous Ocean-Front Paradise!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This feels like your own private resort. Two tiki huts cover lounge chairs and a 13-foot shuffleboard court. The pool an ...
From $575 per night (USD)VRBO
From $139 per night (USD)Expedia
Little Torch Tropical Oasis April Available
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LITTLE TORCH TROPICAL OASIS This Beautiful Oasis is a recently renovated Manufactured Home on the corner of 2 Crystal C ...
From $139 per night (USD)Expedia
From $407 per night (USD)VRBO
ISLAND TIME PARADISE HOUSE!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy breathtaking views of ISLAND TIME PARADISE (our nickname) in Big Pine Key. Its our spacious 3 bedroom 2 bathroom ...
From $407 per night (USD)VRBO
From $171 per night (USD)Expedia
Escape to Eden | Canalfront half-duplex with short run to channel on Big Pine Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean spac ...
From $171 per night (USD)Expedia