Florida Keys Rentals
- From $451 per night (USD)
VRBO
Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $451 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths. Available May 1st for a 6 month rental 2022. Elegant soph ...
From $144 per night (USD)Expedia
- From $125 per night (USD)
VRBO
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $125 per night (USD)VRBO
- From $538 per night (USD)
Expedia
Got stress? 409 Mariners Club has the power to restore you...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Instantly feel the warmth of the island spirit as you enter this recently renovated and refreshed 3-bedroom, 3-bath, tri ...
From $538 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Blue Water Escape 2 bed 2 bath includes Kayak and paddleboard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
House is centrally located in Tavernier and a short boat ride to Tavernier Creek. Tavernier Creek is a gateway to fi ...
From $202 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Spacious Ocean View Suite with Private Kitchen & Balcony! Pool & Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $286 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Nature Retreat Sailboat Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
PLEASE READ! The Salty Conch is a 30ft monohull sailboat that was brought to Key Largo after sailing the Atlantic Oce ...
From $278 per night (USD)VRBO
- From $260 per night (USD)
Expedia
1 br Peaceful Ocean View Retreat in the Florida Keys!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key W ...
From $260 per night (USD)Expedia
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VRBO
Marathon 2BR Deluxe resort on the water w\/ Resort Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For PricingVRBO
- Click For Pricing
VRBO
Feel The Ocean Breeze! Enjoy Family-Friendly Unit | Water Activities Awaits
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
Click For PricingVRBO
- From $2067 per night (USD)
VRBO
Contra House by Brightwild | Luxury Home w\/Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2067 per night (USD)VRBO
- From $431 per night (USD)
Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $431 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Key West Cabana-Old Town Key West- Steps to Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $300 per night (USD)VRBO
- From $318 per night (USD)
Expedia
Fishermen's Paradise- Private Pool, Hot Tub, Quick Access To Ocean, 60 ft Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation in Paradise in our spacious (approx 1,700 sq. ft living space 3 bedroom 2 bath ground level home located in ...
From $318 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Modern Nautical Townhome on Moonbay Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to a piece of paradise! This is a beautiful two-story townhouse that has been newly furnished. Upstairs you will ...
From $350 per night (USD)VRBO
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Expedia
WaterFront community in Islamorada w\/ Marina\/Pool\/Tennis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
20% OFF FROM APRIL-JUNE!!! This 3 bed/2 bath features an open and spacious floor plan! Enjoy king beds, great sound sys ...
Click For PricingExpedia
- Click For Pricing
VRBO
Remodeled Townhome with Beach, Pool, Tennis and Marina!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% APRIL-JUNE!! ...
Click For PricingVRBO
- From $374 per night (USD)
Expedia
🌸Home(#3) BIKINI👙 BOTTOM (Partial View Property-approximately 200 ft from private beach entrance🌸
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
#3: BIKINI BOTTOM 👙Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Coole ...
From $374 per night (USD)Expedia
- From $159 per night (USD)
VRBO
Paradise 201 East Ocean Drive,Key Colony Beach 33051. Minutes to Marathon.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Competently remodeled from quartz countertops in kitchen and both full bathrooms. New doors throughout the unit with up ...
From $159 per night (USD)VRBO
- From $209 per night (USD)
Expedia
The Andros by Brightwild | 4th Floor Sunset View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $209 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Gulf side Gem, 45 ft. Dock, pool , hot tub and more
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the ...
From $325 per night (USD)VRBO
- From $325 per night (USD)
Expedia
DUPLEX IN DUCK KEY, 2 Bedroom \/2 Bath w\/40' Dock, Trailer Storage Incl.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $325 per night (USD)Expedia
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Expedia
Beautiful Ocean Front View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunni ...
Click For PricingExpedia
- From $250 per night (USD)
Expedia
Ocean view condo with balcony\/marina view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in ...
From $250 per night (USD)Expedia
- From $695 per night (USD)
VRBO
Venetian Tropics weekly Pvt home w\/heated Pool, 3 bedroom \/70ft dock w\/canal
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $695 per night (USD)VRBO
- From $475 per night (USD)
Expedia
Watch dolphins play in Shelter Cove while swimming in our olympic size pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelt ...
From $475 per night (USD)Expedia
- From $268 per night (USD)
VRBO
Stunning rooftop views from this gulf side Tuscan style Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougain ...
From $268 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Happy’s Houseboat Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $450 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Silver Shores Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to Silver Shores, one of the most sought after 55 and up communities in the Florida Keys! The Space: T ...
From $135 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Canal front, Dock, Hot Tub and Cabana Club Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. Th ...
From $237 per night (USD)Expedia
- From $103 per night (USD)
VRBO
Key Largo Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful, 2-bedroom, 1 bathroom property located at the entrance to the Florida Keys. Property features full kitchen, 2 ...
From $103 per night (USD)VRBO
- From $441 per night (USD)
Expedia
🌸Home #2: THE REEL WORLD (Off Water Property-approximately 250 ft from Private beach entrance)- 🌸
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming P ...
From $441 per night (USD)Expedia
- From $849 per night (USD)
VRBO
Waterfront Luxury Villa (62) with sunset views and boat slip
- Bedrooms:
- 4
- 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 $849 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful resort located just off the Florida Keys.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For PricingExpedia
- Click For Pricing
VRBO
2 Ocean View Units w\/ Full Kitchens! Enjoy Outdoor Swimming Pool & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
Click For PricingVRBO
- From $555 per night (USD)
VRBO
Relax and Unwind! 2 Family-Friendly Suites To Stay w\/ Swimming Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $555 per night (USD)VRBO
- From $220 per night (USD)
VRBO
El Tesoro a Beautiful 3 Bedroom 2 Bath Marathon Home w\/ Private Pool & Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VACA-23-40 Friday to Friday booking only( Please ask before booking other dates, you will need prior approval or the res ...
From $220 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Private Paradise with Heated Waterfall Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $237 per night (USD)Expedia
- Click For Pricing
Expedia
Amazing Waterfront Gem W\/ Boat Dock, Wraparound Balcony & Full Kitchen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
98th Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingExpedia
- From $198 per night (USD)
Expedia
Stunning Getaway on the Water W\/ Boat Dock, Private Balcony, & Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
98th Street Retreat Side A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $198 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Bohemian Breeze @ Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $297 per night (USD)VRBO
- From $1429 per night (USD)
Expedia
FIN & TONIC Waterfront Condo at The Truman Annex in Key West
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1429 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Villa 5027 on Duck Key BOAT SLIP available
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $219 per night (USD)VRBO
- From $114 per night (USD)
Expedia
Centrally located cottage apartment with patio - walk to beach & dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $114 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Waterfront home with 35-foot dock, Cabana Club membership with pool\/beach access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dream in the Keys Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $275 per night (USD)VRBO
- From $186 per night (USD)
Expedia
Two-story waterfront condo with patio, balconies & boating
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Azure Breeze Villa 2103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $186 per night (USD)Expedia
- From $261 per night (USD)
VRBO
Bonefish Bungalow: 3 BR, 3 BA Townhouse in MARATHON, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Bonefish Bungalow offers an idyllic vacation experience in the captivating Florida Keys, overlooking the picturesque Key ...
From $261 per night (USD)VRBO
- From $185 per night (USD)
Expedia
Cozy condo with free WiFi & fantastic location in central Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Truman @ Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $185 per night (USD)Expedia
- From $213 per night (USD)
VRBO
Private Tropical Beach-No Stairs-Great Location-Heated Pool-Wifi-It's LOADED!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ask me about my Covid-19 cancellation policy. Note: I have been listed on VRBO-Homeaway since 2009. Situated on a Pr ...
From $213 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Beautiful vacation mobile home at the Florida keys.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
You can enjoy a spacious terrace with built in kitchen/bbq, TV and Bluetooth speakers, in a campground resort with plent ...
From $200 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $282 per night (USD)VRBO
- From $195 per night (USD)
Expedia
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Booking for August & September are at a discounted rate of 30%!!! Do not miss out....NEW LISTING. 30-day Minimum Stay. ...
From $195 per night (USD)Expedia
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Expedia
**LADY EMMA IN THE TRUMAN ANNEX, KEY WEST**
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DISCOUNTED RATES FOR SPRING/SUMMER!!!Welcome to Lady Emma which is located in the best location in Old Town, the world f ...
Click For PricingExpedia
- From $612 per night (USD)
Expedia
ELEVATOR*3BR Home*Heated Pool*Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sombrero beach Vacation rental right in the center of Marathon. This Single-Family home has a heated pool and 35ft dock ...
From $612 per night (USD)Expedia
- Click For Pricing
VRBO
Winter Special - Beautiful Waterfront Pool Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
Click For PricingVRBO
- From $395 per night (USD)
Expedia
Coastal Key 3 bed 2 bath with pool kayaks, bikes, paddlebooards and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Vaca-21-256 Sombrero Beach area of Marathon. Beautifully decorated brand new home, located down the street from Sombrero ...
From $395 per night (USD)Expedia
- From $125 per night (USD)
VRBO
Rent a place in Paradise.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A private, Charming 1 bed 1 bath Condo with a full kitchen, heated pool, and spectacular views of the Sunset right from ...
From $125 per night (USD)VRBO
- From $200 per night (USD)
VRBO
A+ Location in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $200 per night (USD)VRBO
- From $942 per night (USD)
VRBO
The Real Liveaboard Experience. Lets go cruising!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is an all private yacht charter. Only your family and friends aboard along with your captains. License To Chill is ...
From $942 per night (USD)VRBO
- From $121 per night (USD)
Expedia
Fish Camp | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this Old Florida-style cottage offering a quintessential retreat for fishing enthusiasts and nature lovers ali ...
From $121 per night (USD)Expedia
- From $281 per night (USD)
VRBO
*Paradise Awaits* Sunshine, Boating, Fishing, RELAXING & RESTING! At It's BEST!*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
My home is perfect for the all around Fishermen,Diving Groups, Family Reunions, Wedding Courts, Diver Certificate Instru ...
From $281 per night (USD)VRBO
- From $494 per night (USD)
Expedia
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $494 per night (USD)Expedia
- From $506 per night (USD)
VRBO
Casa Capri Beautiful Tropical style house with 3 King Suites POOL 2 mi to BEACH
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the b ...
From $506 per night (USD)VRBO
- Click For Pricing
Expedia
Studio in the heart of the Florida Keys, snowbird community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Ocea ...
Click For PricingExpedia
- From $657 per night (USD)
VRBO
AFTERNOON DELIGHT at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $657 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Oceanfront, Snowbird-Friendly Home with High-Speed WiFi, Ocean Views, and Dock
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Humpty Dumpty Hacienda Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $223 per night (USD)Expedia
- From $304 per night (USD)
VRBO
3BR\/3BA Duck Key Island Retreat With Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
In the Heart of the Florida Keys, this three bedroom and three bath Duck Key retreat is located within just minutes of t ...
From $304 per night (USD)VRBO
- Click For Pricing
Expedia
Prince`s Keys Serenity: Canalfront pool home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise with our stunning monthly vacation rental in the Tropical Bay neighborhood on the north side of Big P ...
Click For PricingExpedia
- From $496 per night (USD)
VRBO
3BR\/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon boasting everything you'll need fo ...
From $496 per night (USD)VRBO
- From $2154 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
- Bedrooms:
- 10
- Bathrooms:
- 8
- Sleeps:
- 20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2154 per night (USD)Expedia
- Click For Pricing
Expedia
Luxury Retreat at the Truman Annex near Duval & Beach with Pool, Patio, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Admirals Gold Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
Click For PricingExpedia
- From $258 per night (USD)
Expedia
Dog-friendly home on a wide canal w\/ WiFi & amazing water views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tarpon Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $258 per night (USD)Expedia
- From $335 per night (USD)
VRBO
2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $335 per night (USD)VRBO
- From $213 per night (USD)
Expedia
Airy Top Floor Suite with Ocean Views in Ocean Pointe Near Snorkel \/ Dive Shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $213 per night (USD)Expedia
- From $169 per night (USD)
VRBO
Julia's Secret
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $169 per night (USD)VRBO
- From $338 per night (USD)
Expedia
**BIRD of PARADISE** Elegant Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Like witnessi ...
From $338 per night (USD)Expedia
- From $486 per night (USD)
VRBO
Waterfront Vacation Home w\/Stunning Bay\/Canal Views, Private Dock, Private Beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Casa Koto Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $486 per night (USD)VRBO
- From $1495 per night (USD)
Expedia
Bananas Foster by Brightwild | Epic Guesthouse!
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $1495 per night (USD)Expedia
- From $362 per night (USD)
VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $362 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Spectacular Ocean Front Home In Beautiful Islamorada!<br>Dock,Com Pool, & Prv Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VR-203 We are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with direct a ...
From $600 per night (USD)Expedia
- From $383 per night (USD)
VRBO
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION: 2 KING SUITES, POOLS TENNIS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Please check out our other properties in Kawama by entering the following property numbers in the section "where do you ...
From $383 per night (USD)VRBO
- From $172 per night (USD)
Expedia
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $172 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Luxury Key Largo Home w\/ Guest House & Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Total relaxation awaits you at this Key Largo vacation rental. Located in prestigious Buccaneer Point, this 3-bedroom, 4 ...
From $379 per night (USD)VRBO
- From $669 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $669 per night (USD)VRBO
- From $241 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
- 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 $241 per night (USD)VRBO
- From $562 per night (USD)
VRBO
2x Standard Two Queen Beds at The Gates Hotel Key West, Swimming Pool, Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $562 per night (USD)VRBO
- From $214 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $214 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $217 per night (USD)VRBO
- From $124 per night (USD)
VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + 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! This freshly ...
From $124 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Breezy Beach Waterfront home in Antigua Harbor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Relax in this designer waterfront cul de ...
From $325 per night (USD)Expedia
- From $887 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $887 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $209 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Keys Paradise Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fully furnished, 2 bedroom/ 1 bath mobile home featuring 1 master bedroom with Queen size bed + 1 bedroom with bunk bed ...
From $200 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Villa 5053 on Duck Key BOAT SLIP available
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $219 per night (USD)Expedia
- From $537 per night (USD)
VRBO
Star light, star bright... 403 Mariners Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Starlight star bright...first star I see tonight...I wish I may I wish I might have the wish I wish tonight… And I wish ...
From $537 per night (USD)VRBO
- From $586 per night (USD)
Expedia
Poolside Paradise by Brightwild | Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This 3 bed 2 bath home with a private amazing pool is located right off the quieter end of Duval St. The home c ...
From $586 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Poolside Retreat by Brightwild | Cottage w\/ Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $219 per night (USD)VRBO
- From $219 per night (USD)
Expedia
Lou & Mary`s Getaway ~ 2 bed 2 Bath home W\/Dock, Inch Beach & Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Relax, Fish and Enjoy your stay in this ground level 2 bedroom, 2 bath half-duplex. This Home has easy access to the bay ...
From $219 per night (USD)Expedia
- From $560 per night (USD)
VRBO
25% Discount July & August Special! Reel Sunset 3\/2 with Pool and Canalfront in
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful 3 bedroom 2.5 bath canal front home with private pool. Seaside decor and casual elegance define this comforta ...
From $560 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Updated home with private pool, patio, & grill in enclosed tropical backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $286 per night (USD)Expedia