Florida Keys Rentals
From $241 per night (USD)VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $241 per night (USD)VRBO
From $241 per night (USD)Expedia
Waterfront Home with 33-Ft. Dock and Cabana Club Membership with Beach and Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ninth Street Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $241 per night (USD)Expedia
From $205 per night (USD)VRBO
Waterfront home with private dock, canal views, large terrace & modern kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
La Isla Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $205 per night (USD)VRBO
From $634 per night (USD)Expedia
Two Master Suites! 35' Boat Dockage! Outdoor Living Space & Summer Kitchen!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
At Sombrero Serenity boaters will appreciate the deep water docking out back with room to accommodate up to a 35 ft. boa ...
From $634 per night (USD)Expedia
From $387 per night (USD)VRBO
W04 - 209 Sombrero Beach Rd.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newer built canal front townhouse in the Anglers area of the Sombrero Beach neighborhood. This home features a private h ...
From $387 per night (USD)VRBO
From $450 per night (USD)VRBO
Keys Cottage with Beach and Dockage! Bayfront Property!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Deckhouse" is the perfect beachy cottage for your Keys vacation! It has a full-size kitchen with granite countertops an ...
From $450 per night (USD)VRBO
From $166 per night (USD)VRBO
KCB 1 BD/sleeps-4+Pet friendly+WiFi+Private Cabana Club-Dock on Canal
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our waterfront home is located on 100 foot wide water canal with 30 feet of dockage. We are pet friendly. Furnished with ...
From $166 per night (USD)VRBO
From $326 per night (USD)Expedia
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always ...
From $326 per night (USD)Expedia
From $350 per night (USD)VRBO
Waterfront Cottage - Beach and Dockage! Open Water Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience Keys living the way it used to be! In a world of chain hotels and fabricated experiences, this little slice o ...
From $350 per night (USD)VRBO
From $380 per night (USD)Expedia
Mockingbird Pointe - Waterfront Tropical Escape - Private Home, Pool and Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with priva ...
From $380 per night (USD)Expedia
From $200 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 $200 per night (USD)VRBO
From $221 per night (USD)Expedia
P64 - Spacious 3 bedroom duplex in Key Colony with dockage and Cabana Club...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $221 per night (USD)Expedia
From $95 per night (USD)VRBO
Great Rates! Remodeled Cozy Waterfront Mobile Home In Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally remodeled home located at Eagle Dr in quiet Sexton Cove. 5 minutes away from John Pennekamp State Park, great r ...
From $95 per night (USD)VRBO
From $371 per night (USD)Expedia
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and bea ...
From $371 per night (USD)Expedia
From $229 per night (USD)VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RECENTLY remodeled with beautiful Keys colors. This Lobstering paradise is just 2 houses down from open water on a deep ...
From $229 per night (USD)VRBO
From $556 per night (USD)Expedia
A Taste Of Vitamin Sea 4bed/3bath updated single family with pool, dockage &
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
STR21-000361 Your vacation awaits at A Taste of Vitamin Sea in desirable Key Colony Beach! Vitamin Sea’s canal fronta ...
From $556 per night (USD)Expedia
From $675 per night (USD)VRBO
Elegant Home with Beach & Dockage! Spectacular Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This elegant home, with many unique, architectural features, is located on a beautiful waterfront piece of property, wit ...
From $675 per night (USD)VRBO
From $320 per night (USD)Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $320 per night (USD)Expedia
From $3062 per night (USD)VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $3062 per night (USD)VRBO
From $535 per night (USD)Expedia
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $535 per night (USD)Expedia
From $442 per night (USD)VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $442 per night (USD)VRBO
From $579 per night (USD)Expedia
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $579 per night (USD)Expedia
From $550 per night (USD)VRBO
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
In response to COVID-19, our cottage will be disinfected and sanitized professionally prior to all check-ins. Professio ...
From $550 per night (USD)VRBO
From $233 per night (USD)Expedia
Relax and Unwind in Paradise!! Oceanfront building, 2 bdrm/2ba, Sleeps 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stunning Oceanfront Condo with Beautiful Garden View !! Escape to paradise in this breathtaking oceanfront condo locate ...
From $233 per night (USD)Expedia
From $293 per night (USD)VRBO
Spectacular Open-Water Sunset Views with Boat Slip & Trailer Parking.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful newly refreshed vacation rental is all about the view. It is upstairs with an unobstructed view of the Fl ...
From $293 per night (USD)VRBO
From $387 per night (USD)Expedia
Canal-front home remodeled for HGTV with private swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Pirata Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $387 per night (USD)Expedia
From $351 per night (USD)VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $351 per night (USD)VRBO
From $437 per night (USD)Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $437 per night (USD)Expedia
From $425 per night (USD)VRBO
Waterfront Duck Key Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
From $425 per night (USD)VRBO
From $210 per night (USD)Expedia
Vacation like a local
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $210 per night (USD)Expedia
From $591 per night (USD)VRBO
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are so proud to say our tropical Bungalow now has 65 Straight 5 STAR REVIEWS on VRBO What sets us apart from "just ...
From $591 per night (USD)VRBO
From $429 per night (USD)VRBO
COCONUT in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $429 per night (USD)VRBO
From $195 per night (USD)VRBO
Ocean Shores Lux-Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $195 per night (USD)VRBO
From $225 per night (USD)Expedia
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 $225 per night (USD)Expedia
From $277 per night (USD)VRBO
Near Outdoor Attractions, Spacious Units, Pool and Near Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In this room, there is plenty of space to relax and stretch out. Spacious yet classically structured, the room is cozy a ...
From $277 per night (USD)VRBO
From $545 per night (USD)Expedia
Dog-Friendly Canalfront Home with Dock, Central AC, Fast WiFi, & Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $545 per night (USD)Expedia
From $106 per night (USD)VRBO
Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
White Palm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $106 per night (USD)VRBO
From $462 per night (USD)Expedia
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When your vac ...
From $462 per night (USD)Expedia
From $463 per night (USD)VRBO
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SET SAIL cele ...
From $463 per night (USD)VRBO
From $200 per night (USD)Expedia
Cozy studio cottage in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
From $200 per night (USD)Expedia
From $934 per night (USD)VRBO
Sun of a Beach: Luxurious 7-Bedroom Split-Level Home with private pool, hot tub
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Indulge in the charm of this splendid split-level residence nestled in the heart of the captivating Florida Keys. This d ...
From $934 per night (USD)VRBO
From $211 per night (USD)Expedia
Social distance, work remote (or not at all) in paradise at this beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Very flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, ...
From $211 per night (USD)Expedia
From $273 per night (USD)VRBO
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 $273 per night (USD)VRBO
From $276 per night (USD)VRBO
Comfort and Convenience! Pets Allowed, Free Parking, Tennis Courts, Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $276 per night (USD)VRBO
From $552 per night (USD)VRBO
Just What You Were Looking For! 2 Great Units, Free Parking, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $552 per night (USD)VRBO
Click For PricingExpedia
NEW HOT TUB aboard Houseboat Haven & Pool Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience Key West in a new way: aboard a luxury houseboat! From watching sunrise on the dock to watching suns ...
Click For PricingExpedia
From $739 per night (USD)VRBO
Conspicuous bliss...136 Mariners Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and Atlantic Oc ...
From $739 per night (USD)VRBO
From $1101 per night (USD)Expedia
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $1101 per night (USD)Expedia
From $192 per night (USD)VRBO
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO LITTLE CASITA! If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath hi ...
From $192 per night (USD)VRBO
From $286 per night (USD)Expedia
610 Mariners Club - Budget friendly 1-bedroom!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweet studio apartment in coveted Mariners Club on the island of Key Largo. This is a duplex-style, ground floor 1- ...
From $286 per night (USD)Expedia
From $182 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 $182 per night (USD)VRBO
From $315 per night (USD)Expedia
Waterfront escape with dock, furnished deck & patio, grill & central AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dockside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $315 per night (USD)Expedia
From $258 per night (USD)VRBO
Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tradewinds Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $258 per night (USD)VRBO
From $284 per night (USD)Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $284 per night (USD)Expedia
From $815 per night (USD)VRBO
Ocean's Edge Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Ocean's Edge Retreat is a 3 bedroom / 3 bath home with open water views of the Atlantic Ocean. We have a new saltwater p ...
From $815 per night (USD)VRBO
From $261 per night (USD)Expedia
Old Town Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly redecorated by a one of Key West top interior designers!! Elegant and adorable cottage on one of the nicest lanes ...
From $261 per night (USD)Expedia
From $1251 per night (USD)VRBO
Perfect Location to Key West Action! Garden View, Pool, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1251 per night (USD)VRBO
From $1422 per night (USD)VRBO
Wonderful Stay, Amazing Location! 3 Pools, Bar, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1422 per night (USD)VRBO
From $591 per night (USD)VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! While Old Tow ...
From $591 per night (USD)VRBO
From $1535 per night (USD)VRBO
Fantastic Stay, Best Location! Pool, Bar, Bike Rental, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1535 per night (USD)VRBO
From $1535 per night (USD)VRBO
Tropical Getaway! Pool, Bar, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1535 per night (USD)VRBO
From $754 per night (USD)VRBO
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $754 per night (USD)VRBO
From $754 per night (USD)VRBO
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $754 per night (USD)VRBO
From $221 per night (USD)Expedia
Doc`s Holiday 2bed/2bath half duplex with Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR22-000285 MUST BE 25 OR OLDER TO RENT Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 4 (NO MATTER THE AGE) This ...
From $221 per night (USD)Expedia
From $160 per night (USD)VRBO
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $160 per night (USD)VRBO
From $350 per night (USD)Expedia
Oceanfront! Oceanfront! Oceanfront!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
License # VR-282 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th f ...
From $350 per night (USD)Expedia
Click For PricingVRBO
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq/ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
3rd floor (top level accessible by elevator or stairs) Balcony faces the Atlantic Ocean and gardens. 2 bedrooms (large m ...
Click For PricingVRBO
From $233 per night (USD)Expedia
Play & Stay - Marina Front 2br Condo with Picturesque Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
SEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME. Relax amongst the tropical sights and sounds in this charming oce ...
From $233 per night (USD)Expedia
From $393 per night (USD)VRBO
Angler`s Paradise 2bed/2bath updated half duplex brand new pool & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VACA-22-2 Primary renter must be 25 or older & present for entire stay Seven Night Minimum, No exceptions Max Occu ...
From $393 per night (USD)VRBO
From $681 per night (USD)Expedia
Florida Keys...the island life! 410 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Trip Advisor Award Winner! From your living room or master suite enjoy the expansive view of the Atlantic Ocean and a ...
From $681 per night (USD)Expedia
From $350 per night (USD)VRBO
SOUTHERNMOST SWIM AND SOCIAL CLUB
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $350 per night (USD)VRBO
From $185 per night (USD)Expedia
Fun In The Sun 3 Bedroom House FREE Boat Ramp & Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come relax in Florida Keys Paradise while you enjoy the comforts of a clean 3 bedroom house, (not a mobile home). Centra ...
From $185 per night (USD)Expedia
From $594 per night (USD)VRBO
Treasure Cove- 2BDR/2.5BA Townhouse in Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $594 per night (USD)VRBO
From $208 per night (USD)VRBO
IT'S A SALT LIFE AFTER ALL at the Golf Club in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...
From $208 per night (USD)VRBO
From $218 per night (USD)VRBO
Penthouse view - Futura Yacht Club #604
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6) Enjoy penthouse views of the fabulous blue waters of the Atlantic and Flo ...
From $218 per night (USD)VRBO
From $468 per night (USD)VRBO
Conch home on a quiet lane. Walk to everything. Private swimspa. Dog friendly 🐶🐾
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 2
Recently renovated home located on a quiet lane just 1 block from the iconic Green Parrot Bar and 2 blocks from world fa ...
From $468 per night (USD)VRBO
From $599 per night (USD)VRBO
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $599 per night (USD)VRBO
From $275 per night (USD)Expedia
Luxury cottage in the heart of paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME ABOARD TO ONE OF LARGER COTTAGES ON THE CAMPGROUND. Comfortable and spacious cottage in the center of KEY LARG ...
From $275 per night (USD)Expedia
From $270 per night (USD)VRBO
Breathtaking, Updated, 1325sqft, O/View, Beach, Fishing, Pools, Tennis, 3WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to Experience a Dream Vacation like no other ! Our amazing 1325 sq ft condo has everything you need to Stay, L ...
From $270 per night (USD)VRBO
From $410 per night (USD)Expedia
Blue Vacation Home with private heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This vacation home has a spectacular view over Cudjoe Bay to the Atlantic from the upper deck, and from the seats in the ...
From $410 per night (USD)Expedia
From $403 per night (USD)VRBO
Indigo Reef Resort Waterfront Villa 2 With Boat Dockage, Pool, and Sunset-View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
License # VACA-23-209 - An unforgettable Middle Keys getaway is within reach! The open floor plan welcomes socializing b ...
From $403 per night (USD)VRBO
From $227 per night (USD)Expedia
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
It truly is One of the Best Private Beaches! I can help you find the best, cheapest flights and car rentals. Palm Tree ...
From $227 per night (USD)Expedia
From $544 per night (USD)VRBO
Waterfront luxury Villa (54) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $544 per night (USD)VRBO
From $469 per night (USD)Expedia
Waterfront luxury Villa (43) with spectacular sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $469 per night (USD)Expedia
From $762 per night (USD)VRBO
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $762 per night (USD)VRBO
From $554 per night (USD)VRBO
Beautiful Waterfront Gulf of Mexico Great location.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This property is like having your own private resort. On the Gulf of Mexico. Million-dollar waterfront views & sunsets. ...
From $554 per night (USD)VRBO
From $206 per night (USD)VRBO
A great place to relax, fish, or even work from. 2/2 , 66 ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2 Master suites with great screened in porch overlooking Bayside canal. 66 dock, fully furnished. Large family room with ...
From $206 per night (USD)VRBO
From $475 per night (USD)Expedia
White Vacation Home. Private heated pool, and great view of the Atlantic Ocean.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Kayaks included with the rental. Property has a small floating dock for your boat. We have 2 other homes right next to t ...
From $475 per night (USD)Expedia
From $495 per night (USD)VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $495 per night (USD)VRBO
From $250 per night (USD)Expedia
Yellow Vacation Home. Private heated pool. Water view.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This vacation home is nestled far off of US 1. Kayaks included in the rental. Rent one or both of our other properties t ...
From $250 per night (USD)Expedia
From $228 per night (USD)VRBO
LAMLA's Key Largo's Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
EXPERIENCE KEY LARGO LIVING 🌇 🏊♂️ ⛱ Perfect for a couple's retreat. NO PETS. Enjoy your stay in LAMLA's Key Lar ...
From $228 per night (USD)VRBO
From $237 per night (USD)Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Imagine yourself staying in this immaculate restored home just two blocks away from the H ...
From $237 per night (USD)Expedia
From $356 per night (USD)VRBO
Waterfront luxury Villa (34) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $356 per night (USD)VRBO
From $221 per night (USD)Expedia
Sea-Esta! 2/2 condo, Beach/Pool, Key Colony Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sea-Esta is located on the Atlantic Ocean with a private white sandy beach. If the ocean isn’t calling you, Sea-Esta by ...
From $221 per night (USD)Expedia
From $205 per night (USD)VRBO
Lazy Tortuga 2bed/2bath updated half duplex with Cabana Club & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Tortuga is a ground level luxurious half duplex! This property features 2 bedrooms and 2 bathrooms. The master bedr ...
From $205 per night (USD)VRBO
From $400 per night (USD)Expedia
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $400 per night (USD)Expedia
From $225 per night (USD)VRBO
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, updated home has 2 bedroom and 2 bath, with a large Living/Dining and Kitchen area for entertaining. T ...
From $225 per night (USD)VRBO
From $639 per night (USD)Expedia
3 BEDROOM 3 BATHROOM ISLAND TOWN HOME (ENTIRE HOME)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Named after a famous author and screenwriter who lived around the corner from the resort, these Town Houses are located ...
From $639 per night (USD)Expedia
From $350 per night (USD)VRBO
2 story condo with panoramic bay views and balconies!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This is a 1,350sqft 2 bedrooms/3 bath condo with amazing unobstructed Gulf Bay views. Right next to vaca cut, sunrise an ...
From $350 per night (USD)VRBO
From $490 per night (USD)Expedia
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
2 POOLS, FAST FREE WIFI, SALTWATER SWIMMING LAGOON, 2 KIDS AND 2 JUNIOR KAYAKS, FREE DOUBLE GOLF CART, 2 FREE BICYCLES, ...
From $490 per night (USD)Expedia