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Florida Keys Rentals

From $1216 per night (USD)
VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1216 per night (USD)
VRBO
From $1048 per night (USD)
VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1048 per night (USD)
VRBO
From $1015 per night (USD)
VRBO
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1015 per night (USD)
VRBO
From $3430 per night (USD)
VRBO
4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $3430 per night (USD)
VRBO
From $3747 per night (USD)
VRBO
3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $3747 per night (USD)
VRBO
From $1194 per night (USD)
VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1194 per night (USD)
VRBO
From $2250 per night (USD)
VRBO
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2250 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Waterfront townhome with boat slip, pool, tennis & easy beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nautical Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $234 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $428 per night (USD)
VRBO
From $743 per night (USD)
Expedia
Isla Key Acaí: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $743 per night (USD)
Expedia
From $843 per night (USD)
VRBO
Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $843 per night (USD)
VRBO
$Water view condo with open layout, balcony, well-equipped kitchen, W\/D, & AC$
From $377 per night (USD)
Expedia
Water view condo with open layout, balcony, well-equipped kitchen, W\/D, & AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lighthouse Landing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $377 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $435 per night (USD)
VRBO
From $782 per night (USD)
Expedia
Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $782 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Isla Key Lime: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $443 per night (USD)
VRBO
$Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D$
From $522 per night (USD)
Expedia
Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Key to Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $522 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Island Time in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Go back in “Island” Time, located in the historic Wilhelmina Harvey house, who was the "grand dame of Keys politics" as ...
From $218 per night (USD)
VRBO
$Pelican Perch: updated 2bed\/2ath beachfront condo with shared pool$
From $352 per night (USD)
Expedia
Pelican Perch: updated 2bed\/2ath beachfront condo with shared pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Pelican Perch! This meticulously crafted 2-bedroom, 2-bathroom condo offers an unparalleled blend of luxury ...
From $352 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Bayfront Townhome with Boat Slip, Pool and Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
PROPERTY NAME: Seas The Day 88540 Overseas Highway TH#701, Plantation Key, Florida LOCATION: End unit townhouse on the ...
From $619 per night (USD)
VRBO
From $1102 per night (USD)
VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $1102 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Palms and Pool Paradise
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious Key West retreat in the heart of midtown! This spacious house boasts a private pool, soothing h ...
From $840 per night (USD)
VRBO
From $600 per night (USD)
VRBO
Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! 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 $600 per night (USD)
VRBO
$Brand new, pool\/spa, steps away from beach, elevator, dock\/ice machine sleeps 14$
From $1704 per night (USD)
VRBO
Brand new, pool\/spa, steps away from beach, elevator, dock\/ice machine sleeps 14
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
Exclusive Oceanside Retreat Just Steps from Sombrero Beach. Location: A short, leisurely 5-minute stroll to the beautif ...
From $1704 per night (USD)
VRBO
From $496 per night (USD)
VRBO
Tropical Dream! Pool, Restaurant, Bar, Gym, Bike Rental, Parking!
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 $496 per night (USD)
VRBO
From $2940 per night (USD)
VRBO
VRBO Elite 72' Luxury Motor Yacht
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
New VRBO listing! Be one of the first guests aboard this beautiful, one of kind yacht. You and your guests will have exc ...
From $2940 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Pool, Dock, Dog-Friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Indulge in the ultimate tropical escape at Bayside Beauty, a stunning 3-bedroom home nestled in the exclusive South Poin ...
From $510 per night (USD)
Expedia
From $456 per night (USD)
VRBO
Luxury Modern in Key Largo, Florida with Breathtaking Views
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Welcome to Casa Palma at Rock Harbor, a beautiful and newly remodeled condo located in sunny Key Largo, Florida. Our lux ...
From $456 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Marathon,FL-Indigo Reef #20 RECENTLY UPDATED-LUXURY Villa-waterfront, slip, pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Salty Fare Too (villa 20) at Indigo Reef is located in one of Marathon's best kept secret vacation destinations!! Indig ...
From $530 per night (USD)
Expedia
$Cottage w\/ Bay View FREE Kayaks, Snorkel`$
From $339 per night (USD)
VRBO
Cottage w\/ Bay View FREE Kayaks, Snorkel`
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
The waterfront Captain’s Cottage has a unique layout that accommodates 2 adults and 4 children. There is a small living ...
From $339 per night (USD)
VRBO
$Large House w\/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear$
From $433 per night (USD)
Expedia
Large House w\/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
The Main House is a fully furnished, two-bedroom, 2-floor house facing the bay and can sleep up to 2 adults and 6 childr ...
From $433 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Bayside view Cottage , Free kayaks and sailboat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We call this beautiful Sailfish Cottage our Honeymoon Suite because it is right on the beach and has its own attached ti ...
From $320 per night (USD)
VRBO
$Cottage w\/ Full Kitchen FREE sailboats and kayaks$
From $340 per night (USD)
Expedia
Cottage w\/ Full Kitchen FREE sailboats and kayaks
Bedrooms:
1
Bathrooms:
1
Sleeps:
7
The Owner’s Cottage is waterfront with two bedrooms, which can sleep 2 adults and up to 5 children. The main bedroom has ...
From $340 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Endless Summer Hideaway - lot 181
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Venture Out RV Lot 181 RV Lot 17' Dockage Open Water Views! Open views from this canal front RV lot. Lot features lovel ...
From $216 per night (USD)
VRBO
$Flamingo Flats Ocean Pointe 5306 2BR\/2BA$
From $369 per night (USD)
Expedia
Flamingo Flats Ocean Pointe 5306 2BR\/2BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: New Listing at Ocean Pointe - Escape to the Atlantic in this beautifully decorated condo boasting gorgeous view ...
From $369 per night (USD)
Expedia
$Leisure Inn Islamorada - 3\/2 canal home on a double lot, bring all of the toys!$
From $303 per night (USD)
VRBO
Leisure Inn Islamorada - 3\/2 canal home on a double lot, bring all of the toys!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...second ...
From $303 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Unit 24a - 240 9th Street: 3 BR, 3 BA Duplex in Key Colony Beach, Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Another boring day in the view from this newer stilt half-duplex. This unit has two interior levels. The master bedroom ...
From $325 per night (USD)
Expedia
$Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking$
From $212 per night (USD)
VRBO
Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $212 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Paradise in Key Largo, Amazing outdoor living, pool, electric gate.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy the beautiful Florida Keys in this Key Largo Paradise. This four bedroom, three bath home Has 3 balconies, pool ...
From $460 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Flamingo Cottage! The pretty cottage is located in Islamorada, the heart of the Keys. A part of the interior ...
From $335 per night (USD)
VRBO
From $1019 per night (USD)
Expedia
Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $1019 per night (USD)
Expedia
From $795 per night (USD)
VRBO
Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $795 per night (USD)
VRBO
Click For Pricing
Expedia
Key Largo waterfront home with a pool! Central to all the best attractions!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautifully renovated waterfront home with a screened-in, heated pool situated on an oversized lot in Key Largo. Enjoy n ...
Click For Pricing
Expedia
From $678 per night (USD)
VRBO
Beachfront Duck Key Villa - Sleeps 8. Pet-Friendly!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Relax with family and friends in Duck Key! Located within the heart of the Florida keys our villa will let you explore t ...
From $678 per night (USD)
VRBO
From $564 per night (USD)
Expedia
Ocean View Room Barnacle bed and breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Barnacle Bed and Breakfast, your seaside sanctuary where luxury, comfort and adventure combine seaml ...
From $564 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Ocean Depth Room Barnacle bed and breakfast Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to Barnacle Bed and Breakfast, your oceanfront sanctuary where comfort, luxury, and adventure blend per ...
From $446 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Star Room Barnacle Bed And Breakfast, Big Pine Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to Barnacle, your beachfront haven where comfort, luxury, and adventure merge effortlessly. Enjoy plush ...
From $343 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Gulf front home with 3 bedrooms, pool, hot tub and Dock seconds to open water.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This three-bedroom, two-bath home has a 45-foot dock with ample room for your boat. It is only one house away from the m ...
From $587 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Amazing Yacht With Resort Amenities In The Heart Of Key Largo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Live the real Keys lifestyle with a beautiful 50 foot yacht while having all the benefits of a resort. All hotel ameniti ...
From $457 per night (USD)
Expedia
$MANGROVE HIDEAWAY, KEY LARGO\nCome Enjoy our Piece of Paradise .\n$
From $193 per night (USD)
VRBO
MANGROVE HIDEAWAY, KEY LARGO\nCome Enjoy our Piece of Paradise .\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our Piece of Paradise. This home Features tranquility inside and out with a cozy coastal vibe that you will l ...
From $193 per night (USD)
VRBO
From $1907 per night (USD)
VRBO
Waterfront Resort House + Private boat dock!
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Hosted by a Hilton Hotel General Manager, behold, the most incredible home in all of Key Largo. A private dock attached ...
From $1907 per night (USD)
VRBO
$Ocean Oasis ~ Pool Home w\/ 35` Dock, Walk to Coco Plum Beach!$
From $635 per night (USD)
VRBO
Ocean Oasis ~ Pool Home w\/ 35` Dock, Walk to Coco Plum Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Ocean Oasis Escape to this newly built, stunning 4-bedroom, 3-bathroom vacation home on stilt nestled in the heart of M ...
From $635 per night (USD)
VRBO
From $483 per night (USD)
VRBO
Lofted 1 bedroom suite right off Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to sweet paradise! Located on Petronia Street, the Orange Blossom Suite is in close proximity to all the fun-fil ...
From $483 per night (USD)
VRBO
From $319 per night (USD)
VRBO
The Finn in the Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Finn houseboat has 1 Queen bed. This houseboat has 2 SMART flat-screen TVs and complimentary Wi-Fi. The kitchen feat ...
From $319 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Secluded Tropical Retreat: 60' Dock,Expansive Pool,World-Class Fishing & Lobster
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Finding Remo—a premier luxury retreat nestled within the Great Heron National Wildlife Refuge. This exquisite ...
From $417 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Seabreeze Escape WF RV Lot 489
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Seabreeze Escape WF RV Lot 489 Open Water Views! 35' Dockage with Tropical Landscaping!! Fish and swim right from your ...
From $194 per night (USD)
VRBO
$Relax at The Reef - Pool\/Boat slip\/Kayaks\/Bikes$
From $298 per night (USD)
Expedia
Relax at The Reef - Pool\/Boat slip\/Kayaks\/Bikes
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Summary: Relax At the Reef in this classic Florida Keys style first floor hotel condo. Relax At The Reef is situated rig ...
From $298 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the ultimate in waterfront luxury at Caribbean Cabana, where every moment is a postcard-perfect memory waitin ...
From $333 per night (USD)
VRBO
From $141 per night (USD)
VRBO
COZY HOUSE ON THE WATER, BRING YOUR OWN BOAT.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
DINING IN FRONT OF THE WATER AND RELAXING FROM STRESSFULL LIFE HAVE TO BE A HABIT. BRING YOUR OWN BOAT UP TO 28 FEET. TH ...
From $141 per night (USD)
VRBO
$Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent$
From $266 per night (USD)
VRBO
Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $266 per night (USD)
VRBO
From $981 per night (USD)
Expedia
Tut's Cay: 4 BR, 5.5 BA House in Tavernier, Sleeps 10
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Welcome to Tut’s Cay, an opulent 4-bedroom, 5.5-bathroom sanctuary nestled in the heart of Islamorada within the captiva ...
From $981 per night (USD)
Expedia
From $843 per night (USD)
VRBO
Custom canal-front home with private pool, palapa hut, & outdoor kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Keys Free & Easy Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $843 per night (USD)
VRBO
Click For Pricing
Expedia
Gorgeous 53’ Hatteras yacht on Safe Harbor Channel.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Stay on this gorgeous 53’ Hatteras yacht with cherry wood throughout and a huge salon with everything you need to relax ...
Click For Pricing
Expedia
From $406 per night (USD)
VRBO
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Don’t be fooled by canal front listings. Lose yourself in the ever changing beauty of the Atlantic Ocean in this charmin ...
From $406 per night (USD)
VRBO
$4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview$
From $322 per night (USD)
Expedia
4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $322 per night (USD)
Expedia
From $746 per night (USD)
VRBO
Royal Palm in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
There's no better way to experience island time - that slow shifting of hours that makes Key West such an ideal vacation ...
From $746 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The Florida Keys are located off the southern coast of Florida. They are a string of tropical islands stretching about 1 ...
From $553 per night (USD)
Expedia
From $1697 per night (USD)
VRBO
Gulf-front pool home in the heart of the Keys! Close to the beach! Guest house!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Escape to the tranquil waterways of Serene Sunset Paradise, where aqua waters meet a pristine shoreline and gentle Gulf ...
From $1697 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Cozy Houseboat
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and y ...
From $450 per night (USD)
Expedia
$Key West Home on Golf Course w\/ Patio & Grill!$
From $245 per night (USD)
VRBO
Key West Home on Golf Course w\/ Patio & Grill!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Play a round of golf, snorkel the crystal-clear waters, and explore Key West’s bustling downtown when you stay at this l ...
From $245 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You have found a sandy beach paradise in the Florida Keys! Located just 4 houses from a secret, sandy beach, Little Pea ...
From $245 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Islamorada Slice of Paradise with private beach and glorious sunsets!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully decorated townhome community located right next door to Founder’s Park in Islamorada. This community offer ...
From $241 per night (USD)
VRBO
From $723 per night (USD)
Expedia
A Gulfview Paradise in Key West - Call for more information!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your dream vacation rental in Gulfview Pointe, Key West! This stunning property offers breathtaking waterfron ...
From $723 per night (USD)
Expedia
$Dog-friendly waterfront retreat with dock, private pool, washer\/dryer, patio$
From $503 per night (USD)
VRBO
Dog-friendly waterfront retreat with dock, private pool, washer\/dryer, patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casa Mariner Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $503 per night (USD)
VRBO
Click For Pricing
Expedia
Key West Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Luxurious accommodations, recreational amenities include an outdoor pool, a spa tub, and bicycles to rent. This hotel a ...
Click For Pricing
Expedia
From $422 per night (USD)
VRBO
Mermaid House - Venture Out Lot 089
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Mermaid House - VO089 Ocean Views 35' Dockage 2Bd/2Ba Midrise Covered Porch This vacation home is located right off the ...
From $422 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Cudjoe Cottage - Venture Out Lot 268
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cudjoe Cottage - VO lot 268 This sparkling clean 2 Bedroom 2 full bathroom vacation home is located only 3 lots in from ...
From $444 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Pelicans View - Venture Out Lot 318
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Pelicans View - VO318 Island Gem-Walk to POOL & Marina! Gorgeous Open Water Views! This beautifully remodeled midrise ...
From $327 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with ...
From $520 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Extremely Rare Private White Sand Beach Front Unit on the Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This professionally decorated ocean front unit has everything that you need. 2+2 laundry in unit, upgraded kitchen full ...
From $557 per night (USD)
VRBO
From $694 per night (USD)
Expedia
PARADISE SHORES
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled within the serene surroundings of Islamorada, Florida, awaits a charming oasis at 116 Stromboli Drive. This sing ...
From $432 per night (USD)
VRBO
$Oceanside 5\/4 Home with Heated Pool and Big Dock. Easy access to Ocean and Bay$
From $681 per night (USD)
VRBO
Oceanside 5\/4 Home with Heated Pool and Big Dock. Easy access to Ocean and Bay
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to paradise and everything under the sun! This charming 5/4 has been fully updated. Upstairs is a spacious all ...
From $681 per night (USD)
VRBO
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VRBO
Located on a private beach along the shore, Casa Marina Key West ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Located on a private beach along the shore, Casa Marina Key West ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Located on a private beach along the shore, Casa Marina Key West ...
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Located on a private beach along the shore, Casa Marina Key West, Curio Collection by Hilton is a historic 1920s resort ...
Click For Pricing
VRBO
From $3186 per night (USD)
Expedia
NEW! The Delaney House - Private Pool & Remodeled
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Step into the classic conch cottage known as the Delaney House, situated just half a block from Duval Street. ...
From $3186 per night (USD)
Expedia
From $1848 per night (USD)
VRBO
Perfect for Groups! 2 Pet-friendly Units, Onsite Pool, Beach Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $1848 per night (USD)
VRBO
From $1674 per night (USD)
VRBO
Relax in Paradise! 2 Family-friendly Units, Swimming Pool, Pets are Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $1674 per night (USD)
VRBO
From $1950 per night (USD)
VRBO
Steps from the Ocean! 2 Units, Pets Allowed, Outdoor Pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $1950 per night (USD)
VRBO
From $1618 per night (USD)
VRBO
2 Units in Key Largo's Coastal Charm, Pets Allowed, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $1618 per night (USD)
VRBO
From $2332 per night (USD)
VRBO
Relax and Recharge! 2 Premium Units, Pet-friendly, Beach Access, Onsite Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $2332 per night (USD)
VRBO
From $124 per night (USD)
Expedia
Key Largo Village - 89 Tarpon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Key Largo, enjoy what this 2-bedroom has to offer. With 2 nice queen beds, AC, WiFi, a washing machine, and ...
From $124 per night (USD)
Expedia
From $1545 per night (USD)
VRBO
Ultimate Relaxation! 2 Waterfront Units, Pet-friendly, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $1545 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Nauti Hideaway | Ocean Pointe 2314
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: New listing at Ocean Pointe - this bright and modern condo is ready to help you create life long memories. This ...
From $394 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Aqua Vista Ocean Pointe 3307
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Summary: New Listing at Ocean Pointe - Oceanfront escape with pool, hot tub, marina & beach Enjoy this recently renovate ...
From $414 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Southern Exposure in Cudjoe Key #49
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 1 bathroom home has Panoramic Ocean Views, Southern Exposure, direct oceanfront access with a 45-foot co ...
From $469 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Blue Heaven in Cudjoe Key #99
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spectacular water views from this beautifully maintained 2-bedroom, 2 full bathroom waterfront home located only 4 lots ...
From $534 per night (USD)
VRBO
From $534 per night (USD)
Expedia
Fun in the Sun in Cudjoe Key! #51
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Panoramic Ocean Views! 35' Concrete Seawall to Dock your Boat! This beautifully updated and well-maintained stilt home o ...
From $534 per night (USD)
Expedia
From $639 per night (USD)
VRBO
Tiki Time in Cudjoe Key 136
Bedrooms:
4
Bathrooms:
2
Sleeps:
4
Upscale Oceanfront Retreat! This waterfront gem offers amazing views of the Atlantic Ocean and is the perfect getaway fo ...
From $639 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Paradise Palms in Cudjoe Key #635
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This tropical 2-bedroom, 2 full bathroom home has something for everyone! The kitchen boats new stainless-steel applianc ...
From $320 per night (USD)
Expedia

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