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Florida Keys Rentals

From $802 per night (USD)
VRBO
136 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and Atlantic Oc ...
From $802 per night (USD)
VRBO
From $1018 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $1018 per night (USD)
VRBO
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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 ...
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VRBO
From $318 per night (USD)
Expedia
610 Mariners Club | 1 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweet studio apartment in coveted Mariners Club on the island of Key Largo. This is a duplex-style, ground floor 1-bedr ...
From $318 per night (USD)
Expedia
$Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D$
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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 ...
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VRBO
From $434 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 $434 per night (USD)
Expedia
From $373 per night (USD)
VRBO
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 $373 per night (USD)
VRBO
From $866 per night (USD)
Expedia
Ocean view home with private pool, hot tub, Cabana club and 40 ft dock for boats
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ocean's Edge Retreat is a 3 bedroom / 3 bath home with open water views of the Atlantic Ocean and directly on the canal. ...
From $866 per night (USD)
Expedia
From $794 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 $794 per night (USD)
VRBO
From $901 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 $901 per night (USD)
VRBO
From $459 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 $459 per night (USD)
VRBO
$Doc`s Holiday 2bed\/2bath half duplex with Cabana Club$
From $341 per night (USD)
Expedia
Doc`s Holiday 2bed\/2bath half duplex with Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
This half dupex in Key Colony Beach is situated on the East side of the island, just a short stroll away from the Cabana ...
From $341 per night (USD)
Expedia
$Angler`s Paradise 2bed\/2bath updated half duplex brand new pool & dockage$
From $412 per night (USD)
VRBO
Angler`s Paradise 2bed\/2bath updated half duplex brand new pool & dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the Florida Keys in this lovely two bedroom two bath half duplex located minutes away from beautiful Sombrero Beac ...
From $412 per night (USD)
VRBO
From $774 per night (USD)
Expedia
Mariners Club 410 - Oceanview 3 levels!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Trip Advisor Award Winner! Oceanview from all three levels! From your living room or master suite enjoy the expansive ...
From $774 per night (USD)
Expedia
From $483 per night (USD)
VRBO
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
4
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 $483 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Oceanfront! Oceanfront! Oceanfront!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
License # 24-0123 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th ...
From $408 per night (USD)
Expedia
$Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq\/ft$
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Expedia
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 ...
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Expedia
From $315 per night (USD)
Expedia
Stay & Play; Enjoy Scenic Views Ocean Pointe 5312
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired a ...
From $315 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Enjoy a Fun in the Sun getaway 3 Bedroom House, Tiki Hut, 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). Central ...
From $203 per night (USD)
VRBO
$Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath$
From $601 per night (USD)
Expedia
Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
3
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 $601 per night (USD)
Expedia
From $156 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 $156 per night (USD)
VRBO
From $216 per night (USD)
Expedia
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 $216 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $432 per night (USD)
VRBO
From $327 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 $327 per night (USD)
Expedia
From $308 per night (USD)
VRBO
LUXURY VACATION RENTAL CONDO KEY LARGO TOP AMENITIES & VALUE in the FLORIDA KEYS
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Book your stay with us, and ‘we promise you’, you’ll experience a Wonderful Vacation in the Florida Keys. Our home is ...
From $308 per night (USD)
VRBO
$Blue Vacation Home. Ask about a free pontoon boat rental in our off season.\n$
From $572 per night (USD)
VRBO
Blue Vacation Home. Ask about a free pontoon boat rental in our off season.\n
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 $572 per night (USD)
VRBO
From $416 per night (USD)
VRBO
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Paradise at One of the Best Private Beaches! Let me assist you in finding the best and most affordable fligh ...
From $416 per night (USD)
VRBO
From $556 per night (USD)
Expedia
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 $556 per night (USD)
Expedia
From $729 per night (USD)
VRBO
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 $729 per night (USD)
VRBO
$A great place to relax, fish, or even work from. 2\/2 , 66 ft$
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Expedia
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 ...
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Expedia
From $376 per night (USD)
VRBO
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 $376 per night (USD)
VRBO
From $417 per night (USD)
Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $417 per night (USD)
Expedia
From $508 per night (USD)
VRBO
Yellow Vacation Home. Ask about a free pontoon boat rental in our slow season.
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 $508 per night (USD)
VRBO
From $593 per night (USD)
Expedia
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 $593 per night (USD)
Expedia
$ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool$
From $910 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 $910 per night (USD)
VRBO
From $820 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 $820 per night (USD)
VRBO
From $267 per night (USD)
VRBO
LAMLA's Key Largo's Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
EXPERIENCE KEY LARGO LIVING 🌇 🏊‍♂️ ⛱ Perfect for a couple's retreat. Enjoy your stay in LAMLA's Key Largo's Para ...
From $267 per night (USD)
VRBO
$Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest$
From $288 per night (USD)
Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $288 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Huge Oct savings! Sea-Esta! 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 $270 per night (USD)
VRBO
$Lazy Tortuga 2bed\/2bath updated half duplex with Cabana Club & dockage$
From $291 per night (USD)
Expedia
Lazy Tortuga 2bed\/2bath updated half duplex with Cabana Club & dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Lazy Tortuga is a ground level luxurious half duplex! This property features 2 bedrooms and 2 bathrooms. The master bedr ...
From $291 per night (USD)
Expedia
From $493 per night (USD)
VRBO
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 $493 per night (USD)
VRBO
From $225 per night (USD)
Expedia
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful home has 2 bedroom and 2 bath, a large Living/Dining and Kitchen area for entertaining. The Dining area ...
From $225 per night (USD)
Expedia
From $424 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 $424 per night (USD)
VRBO
From $690 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 $690 per night (USD)
Expedia
From $1410 per night (USD)
VRBO
Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
From the moment you walk up to the covered entryway at Pirate Point, you know you have arrived at your own personal isla ...
From $1410 per night (USD)
VRBO
From $309 per night (USD)
Expedia
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 $309 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Another Day in Paradise Best Waterfront and Poolside Views.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Our Moon Bay Luxury Condominium unit # B403, 4th floor, is located directly on the scenic Blackwater Sound near Florida ...
From $243 per night (USD)
VRBO
From $1638 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $1638 per night (USD)
Expedia
From $525 per night (USD)
VRBO
Villa 5087 on Duck Key BOAT SLIP available
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy the nicest Fully Renovated Villa on Duck Key. Boat slip available for additional $100 a night. Largest boat that ...
From $525 per night (USD)
VRBO
From $605 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 $605 per night (USD)
Expedia
$Key Colony Beach 3\/3 Townhouse - Ocean View$
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VRBO
Key Colony Beach 3\/3 Townhouse - Ocean View
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unit is in mint condition, located in prime Key Colony Beach surrounded by spectacular ocean views. All furnishings are ...
Click For Pricing
VRBO
From $374 per night (USD)
Expedia
Paradise in Beautiful Key Largo!! Amazing Views!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your dream vacation awaits you at Kawama Yacht Club! A unique gated townhome community located in the heart of Key Larg ...
From $374 per night (USD)
Expedia
Click For Pricing
VRBO
P20 - 551 8th St in Key Colony Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to the heart of the Florida Keys! Located in the very desirable Key Colony Beach, this 3 bedroom, 3 bath home is ...
Click For Pricing
VRBO
$Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access$
From $785 per night (USD)
VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $785 per night (USD)
VRBO
$Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite$
From $719 per night (USD)
VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $719 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Sugar Cane - Florida Keys tropical retreat. Newly renovated!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We have just completely renovated this condo at Ocean Pointe and it's Insta-worthy. Every detail has been designed and c ...
From $291 per night (USD)
VRBO
$Absolutely Perfect! Reel Vacation Villa w\/Pool, Dock, Close to Beach w\/Extras!$
From $823 per night (USD)
VRBO
Absolutely Perfect! Reel Vacation Villa w\/Pool, Dock, Close to Beach w\/Extras!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This stunning home on the Intracoastal Waterway is loaded with amenities including a private pool and patio with boat do ...
From $823 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $767 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $767 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Charming Half Duplex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Charming Half Duplex offering 2 bedrooms 2 bathrooms. The home is on a quiet street in a residential neighborhood on a c ...
From $368 per night (USD)
Expedia
From $1436 per night (USD)
VRBO
Sky Suites Retreat, On Duval –2 Stunning Condos
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $1436 per night (USD)
VRBO
From $675 per night (USD)
Expedia
Bright & Cheery Pool Front Home with Ocean Views at Anglers Reef in Islamorada
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $675 per night (USD)
Expedia
From $430 per night (USD)
VRBO
LAST MINUTE SUMMER DEALS! Waterfront Keys Cottage with Amazing Outdoor Living!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sea Salt Cottage is a spacious 3 bedroom 2 bath open concept home on a wide canal with direct access to the ocean. Gues ...
From $430 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Modern-Coastal Spacious Suite [Ocean Pointe 3301]
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Come enjoy this 2 bedroom, 2 bath spacious end suite overlooking the Atlantic Ocean at Ocean Pointe Suites; an ideal des ...
From $344 per night (USD)
Expedia
Click For Pricing
VRBO
Amazing Water Front Pool House & Dock in a very exclusive area!
Bedrooms:
3
Bathrooms:
4
Sleeps:
17
Spectacular home! find the perfect Vacation Rental, two homes in one, with two private entrances , escape to the Flori ...
Click For Pricing
VRBO
From $234 per night (USD)
Expedia
Amazing Ocean view condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly Renovated Beach Décor unit! Breathtaking views of the Atlantic ocean and protected Florida Keys mangroves. Heated ...
From $234 per night (USD)
Expedia
$TORTUGA HAMMOCK -2 Bedroom\/ 2.5 Bathroom Townhouse with Shared Pool & Parking$
From $640 per night (USD)
VRBO
TORTUGA HAMMOCK -2 Bedroom\/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Tortuga Hammock is located on Stock Island in the Coral Hammock private gated community. This 2 bedroom 2.5 bathroom t ...
From $640 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $453 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Tortuga Suite | Sparkling Pool & Hot Tub!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: - Welcome to the quiet & relaxing Sunrise Suites community located on the southeast side of Key West. - Just 1 ...
From $513 per night (USD)
VRBO
From $1027 per night (USD)
Expedia
★Beautiful Modern gated Vacation Oasis★ Private pool & patio close to activities
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Stay in a beautifully modern decorated comfortable gated house with private pool and patio, Carport, large 4K Smart TV ...
From $1027 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Keys Getaway! Located on deep water canal for quick access to
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. ...
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VRBO
From $998 per night (USD)
Expedia
★Welcoming Family Vacation Gated home★with private heated pool and Patio
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a great family vacation in this comfortable gated home offering a private pool and patio, 4K Smart TV's, high spee ...
From $998 per night (USD)
Expedia
From $1018 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $1018 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Ocean view house
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
ocean front, Beautiful island views and sunrise 🌅 view in the morning, had access for the boat , kayaking, paddle ...
From $469 per night (USD)
Expedia
$Ocean Front 2\/2 Condo,OCEAN FRONT\/MARINA VIEW,Tavernier\/Key Largo Fl. Fla.Keys$
From $333 per night (USD)
VRBO
Ocean Front 2\/2 Condo,OCEAN FRONT\/MARINA VIEW,Tavernier\/Key Largo Fl. Fla.Keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Paradise! Discover the pinnacle of luxury at Ocean Pointe, a premier resort nestled in Tavernier, Florida Key ...
From $333 per night (USD)
VRBO
From $562 per night (USD)
Expedia
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
** The Marina is repairing some of the boat slips currently BUT you can reserve one at the marina right there for an add ...
From $562 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This gorgeous 3 bedroom 3 full bath townhouse is located in the tropical neighborhood of Kawama. This unit underwent a f ...
From $568 per night (USD)
VRBO
From $551 per night (USD)
Expedia
Manatee Watch | Gorgeous pool, 5 bedrooms, easy ocean access on Big Pine Key
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offer ...
From $551 per night (USD)
Expedia
From $351 per night (USD)
VRBO
P23 - New 3 bedroom 2 bath duplex with private pool and deep water dockage.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This all ground level home boasts ease of access inside and out, with an open floor plan and a large, fully equipped kit ...
From $351 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Serene Sunsets Await - Tropical Island Getaway Without The Extensive Travel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BOAT SLIP Available for ALL Lobster Seasons..! July 2024 Updates: Unbelievable...! Word to describe the upgrades all ...
From $313 per night (USD)
Expedia
$Enjoy the keys updated 3\/2home on a canal in marathon 7 day min disc for 30days+$
From $314 per night (USD)
VRBO
Enjoy the keys updated 3\/2home on a canal in marathon 7 day min disc for 30days+
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A fisherman's dream boat dock freezers for your catch commercial icemaker fish cleaning station backyard grill fully s ...
From $314 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
NEWLY RENOVATED AND...… GORGEOUS! SLEEPS 6 Thank you for viewing our gorgeous Coral Lagoon 3 bedroo ...
From $614 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Villa Jekjak | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive ...
From $397 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Beautiful updated Kawama Townhouse. Two units available. Second unit #1306961.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This gorgeous 3 bedroom 3 full bath townhouse is located in the tropical neighborhood of Kawama. This unit underwent a ...
From $572 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful & Relaxing 2 bed 2 bath condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a large 2 bed 2 bath condo with a separate living room, kitchen, and private balcony at the Hyatt Resort. It off ...
Click For Pricing
VRBO
From $525 per night (USD)
Expedia
Island Adventure I 4 Bedrooms 4.5 Baths, Pool, Ocean View with Dock & Kayaks
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
VACA-22-75 "Island Adventure" was built-in 2021, with Family, Fun, Luxury, and Water Sports Lovers in Mind. The home is ...
From $525 per night (USD)
Expedia
$Aqua Lodge Houseboat \Sea Turtle\$
From $354 per night (USD)
VRBO
Aqua Lodge Houseboat \"Sea Turtle\"
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to The Aqua Villas at Mangrove Marina Resorts “Sea Turtle” houseboat, located between Key Largo and Islamorada i ...
From $354 per night (USD)
VRBO
From $731 per night (USD)
Expedia
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated a ...
From $731 per night (USD)
Expedia
From $1340 per night (USD)
VRBO
All Included!!Private 3bedSailboat IncludingAccommodations&AllExcursions up to 6
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome aboard the The Thirsty Lady with 3 bedrooms and 3 baths, your own private Sailboat that also includes your Saili ...
From $1340 per night (USD)
VRBO
From $291 per night (USD)
Expedia
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 $291 per night (USD)
Expedia
$Aqua Lodge Houseboat \Calypso\$
From $520 per night (USD)
VRBO
Aqua Lodge Houseboat \"Calypso\"
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
It doesn’t get much more unique than the Aqua Villas at Mangrove Marina. Come experience the adventure of living on the ...
From $520 per night (USD)
VRBO
$Aqua Lodge Houseboat \Captain's Quarters\$
From $489 per night (USD)
Expedia
Aqua Lodge Houseboat \"Captain's Quarters\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Aqua Villas at Mangrove Marina Resorts “Captain’s Quarters” houseboat, located between Key Largo and Isla ...
From $489 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Sunsets over the water
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sunset views over the water has this large 1/1 with 1 assigned parking space. Only a few minutes from the Island of Key ...
From $144 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Anchor's Away - Your Waterfront Haven in Marathon! Escape to Anchor's Away, your charming waterfront sanctua ...
From $276 per night (USD)
Expedia
From $521 per night (USD)
VRBO
Spectacular Water Front Home! Key Largo, Ocean side, Sea Breeze
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Breathtaking concrete home with 2,200SF A/C and 6,900SF lot, freshly remodeled with elegance having large impact windows ...
From $521 per night (USD)
VRBO
$Aqua Lodge Houseboat \The Grey Lady\$
From $592 per night (USD)
Expedia
Aqua Lodge Houseboat \"The Grey Lady\"
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This houseboat has 2 Queen beds, 1 Double bed and 1 Twin bed. The houseboat has a flat-screen TV with cable in the livin ...
From $592 per night (USD)
Expedia
From $212 per night (USD)
VRBO
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 $212 per night (USD)
VRBO
$Casa Playa | 4 bed\/2 bath canalfront getaway on Ramrod Key$
From $223 per night (USD)
Expedia
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 $223 per night (USD)
Expedia
From $403 per night (USD)
VRBO
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
As you step through the door, you are enveloped in a serene atmosphere highlighted by soothing tropical colors and impre ...
From $403 per night (USD)
VRBO
From $697 per night (USD)
Expedia
Key West Beach House with heated pool, tiki, and dock.♿︎
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Key West. Located on this beautiful island 13 miles from downtown is this quaint 2-level beach home. With sle ...
From $697 per night (USD)
Expedia

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