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From $348 per night (USD)
VRBO
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $348 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Island Time Escape – Resort Stay #405, Island Time Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cozy Pool Resort Condo with Tiki & Dining – Marathon, FL Enjoy island living in this 5-star condo with King master bedro ...
From $306 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Captain & Mermaid Diamond #BP25
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Seafront Tropical Retreat – Big Pine Key Getaway Escape to this serene waterfront oasis in Big Pine Key, just 30 miles f ...
From $159 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $313 per night (USD)
VRBO
From $203 per night (USD)
VRBO
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Charming water front bungalow 40ft Dock & Tiki in the heart of Key Largo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the heart of the Florida Keys. Come relax, play, and stay in Key Largo. Our house is perfect for families &am ...
From $125 per night (USD)
Expedia
From $247 per night (USD)
VRBO
JUNE-AUG 2025 DISCOUNT! - 2 Bedroom FL Keys Canal Home - Great Boating Access!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Pirates Quay! This newly remodeled 2 bedroom home in Little Torch Key is one of the nicest, most thought-out ...
From $247 per night (USD)
VRBO
From $359 per night (USD)
Expedia
2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Gecko House! This canal-front 2 bedroom, 2 bath house is located in a great boating area with easy access to ...
From $359 per night (USD)
Expedia
From $425 per night (USD)
VRBO
JULY 2025 DISCOUNT!!! - 3 Bedroom/2 Bath Canal Home w/ Private Pool - Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Reel Life, a beautiful Cudjoe Gardens Oasis! Located on the ocean side of Cudjoe Key, this home has everythin ...
From $425 per night (USD)
VRBO
From $652 per night (USD)
Expedia
The Roost in Summerland Cove Isles
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The Roost in Summerland Cove Isles affectionately know as 'The Castle' is truly a gem nestled in a highly desirable neig ...
From $652 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Sombrero Beach Tropical Getaway in the Heart of Marathon
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the beauty of Marathon from this marvelous 1-bedroom condo. This tranquil retreat features a king bed in the be ...
From $392 per night (USD)
VRBO
From $220 per night (USD)
Expedia
OPEN FOR 2025 LOBSTER SEASON! Nice 2-bedroom Canal Home in serene Big Pine Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Big Pine Breeze! This charming 2 bedroom/2 bathroom home is located just one canal from open water making it ...
From $220 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This Marathon condo boasts 1 inviting bedroom. The living room features a cozy sofa bed for extra guests. Guests can enj ...
From $383 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Amazing new 2-bedroom, 2-bathroom apartment in the heart of Islamorada!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Islamorada apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room also offers an extra queen ...
From $219 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Spacious Key Largo Home with Dock with Fast Ocean Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your cozy getaway awaits in Key Largo at this gorgeous house. With 3 bedrooms including 1 king bed, 2 queen beds, 1 bunk ...
From $590 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Canal front pool home in Florida key's Islamorada! Access to ocean w/boat lift!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Luxury Waterfront Vacation Home in Islamorada Escape to paradise in this stunning waterfront vacation home located in t ...
From $522 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Renovated waterfront duplex with canal access, deck, water views & central AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bohemian Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $286 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Cozy home with outdoor shared pool, central AC, internet
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Villa del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $390 per night (USD)
Expedia
From $192 per night (USD)
VRBO
The Perfect Getaway is an upscale oasis for you and pets to relax and have fun!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Our stylish home will place you close to everything but provide comfort and relaxation for both people and pets alike. ...
From $192 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: The excitement of America’s Caribbean, the Florida Keys, awaits you at Island Time! This designer decorated and ...
From $288 per night (USD)
Expedia
From $467 per night (USD)
VRBO
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $467 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Sombrero Getaway: Poolside Retreat with Canal Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to your tropical oasis in the heart of paradise! This spacious 4-bedroom, 3-bathroom vacation home is the perfec ...
From $505 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Tavernier Canal front Retreat with Boat Lift – 28-Day Keys Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Your Tavernier Canal front Retreat! Escape to the Florida Keys for a serene 28-day stay in our charming 2-bed ...
From $253 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Beautiful Home located in Downtown Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
PROPERTY NAME: Mango House 81212 Old Highway Islamorada, Florida Location: Ocean side located on the Old Road by Gree ...
From $204 per night (USD)
Expedia
Click For Pricing
VRBO
Got Stress? You Need KeyBliss - The BEST Bayfront Unit in Buttonwood Bay
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This beautiful end unit is nestled in the most charming area of the best condominium complex in Key Largo. As you walk u ...
Click For Pricing
VRBO
From $203 per night (USD)
Expedia
Endless Summer Retreat: Dog-Friendly 3BR Canal Front Oasis, Dockage & Easy Atlantic/Gulf Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $203 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Open Water Modern Home 2/2
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RARE FIND OPEN WATER VIEWS FROM ALL ANGLES AND DECK! Located on Little Torch Key 28.5 mm Jolly Roger Estates. Meticulous ...
From $433 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Enjoy the ocean breeze from this beautiful top floor condo. This unique model has 2 balconies and is located on ...
From $276 per night (USD)
Expedia
From $579 per night (USD)
VRBO
Sombrero Siesta: Heated Pool & Stunning Canal Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Sombrero Siesta, your ultimate tropical getaway in the heart of the Florida Keys! This luxurious canal-front ...
From $579 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Water front 2-bedroom home in Key Largo with AC, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Water front deep water canal 2 bedroom 1 bath comfortable and modern entire home in Key Largo. Parking for boat and trai ...
From $224 per night (USD)
Expedia
From $637 per night (USD)
VRBO
Walk to Beach: Waterfront Home in Marathon!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Kayaks & Paddleboard | Tropical Hut w/ Grill | Private Pool & Boat Dock | Pet Friendly w/ Fee Feel your worries drift a ...
From $637 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Ocean Side Paradise Awaits!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic O ...
From $204 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Ocean Isles Seaside Oasis
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Welcome to paradise! This new 1 bed/2 bath is centrally located in Marathon. The condo is steps away from open ocean vie ...
From $205 per night (USD)
VRBO
From $398 per night (USD)
Expedia
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $398 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Florida Keys Marathon #211 Cozy waterfront 1 bdrm condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
You’re not in Florida, You’re in Paradise "The Keys", the American Caribbean! We are now accepting reservations for 2025 ...
From $294 per night (USD)
VRBO
From $176 per night (USD)
VRBO
Florida Keys Marathon #205 Cozy Waterfront 1-bedrm condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You’re not in Florida, You’re in Paradise "The Keys", the American Caribbean! We are now accepting reservations for 202 ...
From $176 per night (USD)
VRBO
From $125 per night (USD)
VRBO
Serene Key West Studio with Poolside Peace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Boater's Paradise ! Enjoy the sunsets from your covered patio...
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Want to make a special arrangement? If you are a repeat customer, please contact me for special rates ! This tropical g ...
From $223 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Paradise Palms~ Waterfront Oasis w/ 40' Dock, Pool, Open Water Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Property Highlights: • Sleeps: 8 • Bedrooms: 3 • Bathrooms: 3.5 • Parking: This property features 6-8 parking spaces fo ...
From $688 per night (USD)
VRBO
From $4316 per night (USD)
Expedia
**CASSIE’S PARADISE @ SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The vacation opportunity of a lifetime awaits at CASSIE’S PARADISE. A secluded oceanfront experience, this breathtaking ...
From $4316 per night (USD)
Expedia
From $276 per night (USD)
VRBO
VIRGINIA VISTA - Steps from Duval, 2B/R, 2 Bath Retreat with Pool & Large Porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval on Virginia Street, VIRGINIA VISTA occupies the upper level of an almost 100-year-old home i ...
From $276 per night (USD)
VRBO
From $260 per night (USD)
VRBO
VIRGINIA VERANDA, Stylish Old Town 2 B/R, 2Bath, with Pool, Steps from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-ol ...
From $260 per night (USD)
VRBO
From $685 per night (USD)
VRBO
3-bedroom townhome in Key West with fitness room, WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $685 per night (USD)
VRBO
From $1583 per night (USD)
Expedia
Ocean Paradise Point 12
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to this brand new, coastal modern 3-bedroom, 2.5-bathroom home located in a gated, intimate community right on th ...
From $1583 per night (USD)
Expedia
From $819 per night (USD)
VRBO
Atlantis House Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled within the serene enclave of the Atlantis House Compound, the Palm and Banyan Suites offer a tropical oasis for ...
From $819 per night (USD)
VRBO
From $637 per night (USD)
Expedia
Coco's Poolside Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $637 per night (USD)
Expedia
From $1409 per night (USD)
VRBO
The Flower Power House - Boho Beautiful
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $1409 per night (USD)
VRBO
From $1318 per night (USD)
Expedia
Luxury 5BR Home in Marathon w/ Bay Views, Boat Dockage, Pool, Outdoor Living
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Your Private Florida Keys Escape – Luxury 5BR Bayfront Oasis in Marathon Discover the ultimate coastal getaway at this ...
From $1318 per night (USD)
Expedia
$4 bed 2 bath\/Canal front\/Dockage\/ Port Largo$
From $279 per night (USD)
VRBO
4 bed 2 bath\/Canal front\/Dockage\/ Port Largo
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your dream getaway in the heart of Key Largo! This beautifully renovated 4-bedroom, 2-bathroom home offers a ...
From $279 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
County zoning regulations require a minimum rental period of 28 nights, and no exceptions can be made. Please review add ...
From $365 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Garden of Roses | Private Hot Tub, Prime Key West Location! Experience the essence of Key West living at Garden of Rose ...
From $213 per night (USD)
VRBO
From $623 per night (USD)
Expedia
Casa Cayo: 4 bedroom home with pool and dockage
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Casa Cayo, a luxurious vacation rental in Coco Plum! The home includes two identical master suites with en-s ...
From $623 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $149 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Ritaville | New! Waterfront Paradise with Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Ritaville | New! Waterfront Paradise with Private Pool Experience a serene retreat at Ritaville, a stunning waterfront ...
From $372 per night (USD)
Expedia
From $486 per night (USD)
VRBO
The Salty Seahorse- Pristine Private Pool, Game Room & Cabana Club Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Salty Seahorse Time to relax at this modern coastal 3 bedroom, 3 bathroom duplex with 25 ft of boat dockage and a beau ...
From $486 per night (USD)
VRBO
From $311 per night (USD)
VRBO
Paradise away from home.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious paradise features a large living area with windows that flood the space with natural light, while the kitc ...
From $311 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Gone Coastal @ Ocean Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience the ultimate island getaway, complete with all the fun and relaxing resort amenities you could ever ...
From $252 per night (USD)
VRBO
Click For Pricing
Expedia
Wander Islamorada Shores w/ Ocean View – 4 Bedrooms, Sleeps 8
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Wander Islamorada Shores is a stunning coastal escape with 180-degree Atlantic views. This home features four-bedroom en ...
Click For Pricing
Expedia
From $659 per night (USD)
VRBO
Cozy home with water access, private pool, dock, wifi, central a/c, balcony
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Coco Plum Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $659 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Gypsyginny's Hideaway in downtown Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Set in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Stree ...
From $236 per night (USD)
Expedia
From $507 per night (USD)
VRBO
Waterfront 5 Bedroom Mansion with Pool&Dock
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Escape to a luxurious waterfront oasis located at Key Haven, just a stone's throw from Key West. Bring your boat up to 3 ...
From $507 per night (USD)
VRBO
Click For Pricing
Expedia
Charming 2-bedroom house with WiFi, AC in delightful Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in Key Largo, this charming house features 2 queen bedrooms, each equipped with a hair dryer for your convenienc ...
Click For Pricing
Expedia
From $311 per night (USD)
VRBO
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Palm Isle! A tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front ...
From $311 per night (USD)
VRBO
From $1344 per night (USD)
Expedia
Key Largo luxurious coastal Retreat endless views Pets OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this brand new, coastal modern 3-bedroom, 2.5-bathroom home located in a gated, intimate community right on th ...
From $1344 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location Duval Hideaway is the perfect home base ...
From $450 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking Duval Street Retreat is your ideal Key W ...
From $474 per night (USD)
Expedia
From $1523 per night (USD)
VRBO
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Meadows Manor | Elegant Oasis with Private Pool & Parking Discover the perfect blend of luxury and tranquility at the M ...
From $1523 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, Close to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, and Close to Beach! Salt Pond Hideaway is your ideal retreat ...
From $376 per night (USD)
Expedia
From $894 per night (USD)
VRBO
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking Southernmost Retreat is the perfec ...
From $894 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Kingfish Keep | Lively Escape on Duval! Balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Kingfish Keep | Lively Escape on Duval! Balcony! Kingfish Keep is the perfect escape in the heart of the historic distr ...
From $330 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Yellowfin Ledge | Inviting Getaway On Duval! Balcony! Yellowfin Ledge is the ideal choice for your Key West adventure! ...
From $279 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Wahoo Way | Charming Hideaway On Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wahoo Way | Charming Hideaway On Duval Street! Escape to Wahoo Way for an unforgettable couple’s retreat in Key West! T ...
From $280 per night (USD)
Expedia
From $900 per night (USD)
VRBO
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street! Pescado Penthouse is the ultimate getaway for families or ...
From $900 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront Resort, New Year’s Eve, 7 Nights, Sleeps 6, Pool, Hot Tub, Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for celebrating New Year’s Eve in sunny Key West, FL? You will be staying at the H ...
Click For Pricing
Expedia
From $187 per night (USD)
VRBO
Cozy 2BR Retreat with Hot Tub!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your ideal living space! This beautifully furnished upstairs unit boasts a clean and open living area, perfec ...
From $187 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Winter Escape, Modern 3-bedroom plus Loft, Heated Pool, Beach, Fishing Pier
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy a warm winter in the Florida Keys at this beautifully furnished 3-bedroom, 2.5 bathroom townhouse with bonus loft ...
From $234 per night (USD)
Expedia
From $1594 per night (USD)
VRBO
Paradise Point 11- New 3 bed 3 bath Oceanfront home rooftop balcony- Pets OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to this brand new, coastal modern 3-bedroom, 3-bathroom home located in a gated, intimate community right on the ...
From $1594 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Octopus Oasis: Escape to 4BR Canal-Front Retreat in Marathon, Dockage & Quick Atlantic Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
City of Marathon zoning requires a minimum rental period of 7 nights, and no exceptions can be made. Please review addit ...
From $335 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap ...
From $381 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Summerland Sanctuary: 3BR Canal Front Retreat with Private Pool, Dockage & Premier Boating/Fishing
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $261 per night (USD)
Expedia
From $660 per night (USD)
VRBO
Key West Paradise 3-bedroom townhome w/large shared pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Perfect for family getaways or group trips, this spacious townhome offers plenty of room for everyone to enjoy. It featu ...
From $660 per night (USD)
VRBO
From $585 per night (USD)
Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $585 per night (USD)
Expedia
From $312 per night (USD)
VRBO
3-bedroom House in tranquil Islamorada with Modern Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make yourself at home in this 3-bedroom Islamorada retreat. This charming house features 2 queen beds and 2 full beds, p ...
From $312 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Island Breeze Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Island Breeze Escape – Your Key Largo Paradise Awaits Step into the ultimate Florida Keys experience at Island ...
From $234 per night (USD)
Expedia
From $387 per night (USD)
VRBO
A409 Moon Bay 2 Bedrooms, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
7-night minimum stay requirement Welcome to this fully remodeled, stunning condo, where no detail has been overlooked. ...
From $387 per night (USD)
VRBO
From $222 per night (USD)
Expedia
WASTIN' A WAYLAND ~ Renovated 2 BR/2 Ba Home in Old Town!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OLD TOWN GEM... This 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a ...
From $222 per night (USD)
Expedia
From $2060 per night (USD)
VRBO
**HOUSE OF THE ROYAL PALMS @ OLD TOWN** Estate & Pool Near Duval + LAST KEY SERV
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $2060 per night (USD)
VRBO
From $1111 per night (USD)
Expedia
**The Three Mermaids @ Solaris Hill** New Construction Compound + Last Key Servi
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finding a com ...
From $1111 per night (USD)
Expedia
From $691 per night (USD)
VRBO
Ocean on 6th
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Until 2017, this was a very popular vacation rental know as the 'Million Dollar Baby". It was completely renovated from ...
From $691 per night (USD)
VRBO
From $467 per night (USD)
Expedia
At The Sandbar: Oceanfront, Htd Pool, Free Dockage, GameRoom, EV Charger
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Amenities: Free boat dockage, htd pool, BBQ grill, EV charger 🏓 Game room 📍 Mins to the famous ...
From $467 per night (USD)
Expedia
From $316 per night (USD)
VRBO
INTO THE BLUE~GRAND OPENING RATES! Pristine 4 BR/3.5 BA Home w/Private Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
TOP NOTCH LIVING… Nestled in the exclusive Casa Marina district, this newly constructed sanctuary sits only a few blocks ...
From $316 per night (USD)
VRBO
From $328 per night (USD)
Expedia
🌴 TROPICAL RETREAT 🌴 RV in the Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tropical retreat in the heart of Florida Keys. Relax island-style in this private updated RV - just 30 miles from Key We ...
From $328 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Oceanfront Luxury Condo with Panoramic Views & Designer Finishes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $260 per night (USD)
VRBO
From $350 per night (USD)
Expedia
3 Rooms Stunning Paradise Waterfront Getaway! Ocean access in Key Largo Florida.
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to your home away from home in Key Largo! This charming waterfront property offers 3 comfortable bedrooms: one w ...
From $350 per night (USD)
Expedia
From $726 per night (USD)
VRBO
Luxurious 3-bedroom home with Pool and Dock in Key Colony Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Luxurious Waterfront Oasis in the Florida Keys Welcome to your dream retreat in the heart of the Florida Keys! This stu ...
From $726 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Azul Paradise - Waterfront - Heated Pool - Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Experience modern coastal luxury at Azul Paradise, a stunning 3BR 2BA waterfront home in Marathon, FL. Enjoy a ...
From $474 per night (USD)
Expedia
From $986 per night (USD)
VRBO
Key Largo Oasis Oceanfront with Pool & Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Welcome and enjoy the waterfront serenity and modern amenities at our newly constructed Oceanview Paradise! Start your ...
From $986 per night (USD)
VRBO
From $1270 per night (USD)
Expedia
New Oceanside Paradise with Pool and Waterfront Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Welcome to the breathtaking ocean views of Key Largo Oceanside! Explore the serene waters with kayaks and paddleboards ...
From $1270 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Private Pool & Dock: Waterfront Key Largo Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Walk to Ocean, Shops & Restaurants | Canal Views | Pet Friendly (w/ Fee) Kick back and relax 'on island time' at this c ...
From $241 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Lanai, Pool & Patios: Waterfront Home in Tavernier
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Pets Welcome w/ Fee | 3 Outdoor Dining Areas | Free WiFi | 1 Mi to Harry Harris Beach Endless outdoor fun awaits at thi ...
From $228 per night (USD)
Expedia

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