Key West Rentals
From $297 per night (USD)VRBO
Minutes away from beaches, Old Town, dining and all the best of Key West!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sunset Serenity, a beautifully appointed 3-bedroom, 3-bath island home offering the perfect blend of modern c ...
From $297 per night (USD)VRBO
From $441 per night (USD)Expedia
Key West Riviera Paradise Canal Front 3BR w/ Private Pool & Boat Access 1Pet OK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your Private Key West Waterfront Oasis Live like a local in this private Key West hideaway—a cozy, canal-front retreat ...
From $441 per night (USD)Expedia
From $1061 per night (USD)VRBO
Enjoyable 2-bedroom Hyatt Beach House condo in Key West during Fantasy Fest!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Key West, this condo is an enchanting retreat. With two spacious bedrooms featuring king beds, guests enjoy p ...
From $1061 per night (USD)VRBO
From $219 per night (USD)Expedia
Old Town Hideaway close to Historic Seaport and Duval St. Heated/chilled pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Key West at this charming house perfect for a relaxing getaway. With three bedrooms featuring a queen, king, a ...
From $219 per night (USD)Expedia
From $558 per night (USD)VRBO
The Margaret Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Stay in the heart of Old Town at The Margaret Suite, a bright studio in historic Bayview House. Ideal for coup ...
From $558 per night (USD)VRBO
From $5378 per night (USD)Expedia
Lighthouse Suites Collection
- Bedrooms:
- 7
- Bathrooms:
- 10
- Sleeps:
- 30
Summary: 9BD/7BA Entire Boutique Resort. Steps from Duval with Two Oasis Pools, Private Porch, Outdoor Bar & Grill, & P ...
From $5378 per night (USD)Expedia
From $1191 per night (USD)VRBO
The Grand Tiki at Tiki Suites – A Floating Oasis in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience one of Key West’s most extraordinary and unforgettable getaways at The Grand Tiki at Tiki Suites — a truly un ...
From $1191 per night (USD)VRBO
From $816 per night (USD)Expedia
Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Leave reality behind and experience one of America's coolest overwater stays. Safely anchored on the shallow, pristine b ...
From $816 per night (USD)Expedia
From $254 per night (USD)VRBO
3-bedroom house boat in tranquil Key West with AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The paired pontoon boat with this stay is a separete payment from your stay payment and is required within 7 days of the ...
From $254 per night (USD)VRBO
From $161 per night (USD)Expedia
Charming Old Town Studio- Steps to Duval Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to “The Coconut” – Your Slice of Old Town Paradise Tucked into the heart of Old Town Key West, The Coconut is ...
From $161 per night (USD)Expedia
From $458 per night (USD)VRBO
Monthly rental-1 level, 4-bed, 3 bath, quiet home, private sunny pool, parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Available for 28 night minimum stays only, due to Key West regulations. In high season (Nov.-April) If you are renting f ...
From $458 per night (USD)VRBO
From $300 per night (USD)Expedia
1 bedroom Sleeps 4 - Fantasy Fest Week Oct 17 - 24
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The resort sits on the water. Reservation is based on a full week. you don’t have to stay the week, but the price for th ...
From $300 per night (USD)Expedia
From $533 per night (USD)VRBO
Entire Townhouse Pool Front in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Step inside this spacious Key West townhouse featuring 3 large bedrooms and 3 full bathrooms, thoughtfully laid out acro ...
From $533 per night (USD)VRBO
From $228 per night (USD)Expedia
Back to the Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The front door to this second floor 1 bedroom / 1 bath vacation spot opens to a perfect lesson in space mastery and hist ...
From $228 per night (USD)Expedia
From $592 per night (USD)VRBO
Luxury Residence in Old Town Key West w Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to The Watson House, a historic gem at 522 Simonton Street, where old-world luxury seamlessly blends w ...
From $592 per night (USD)VRBO
From $1057 per night (USD)Expedia
Tranquil tropical 3-bedroom house with AC in vibrant Key West.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 3-bedroom Key West house. The enchanting space features a king bed, queen bed, and twin be ...
From $1057 per night (USD)Expedia
From $341 per night (USD)VRBO
Island Time Escape - Charming Family Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Dedicated Key West Retreat with Pool & Separate Cabana Welcome to your own Key West retreat! This spacious 3-bedro ...
From $341 per night (USD)VRBO
From $478 per night (USD)Expedia
Wahoo Watch Two Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Coconut Mallory Resort and Marina by KEES Vacations Just a mile from Key West International Airport, 3 ...
From $478 per night (USD)Expedia
From $373 per night (USD)VRBO
Yellow Fin Fantasy One bedroom Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Yellow Fin Fantasy! Start your incredible Florida Keys experience by relaxing among the sunshine and pa ...
From $373 per night (USD)VRBO
From $478 per night (USD)Expedia
Hogfish Hideaway Two Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Hogfish Hideaway! Just a mile from Key West International Airport, 3 miles from vibrant Duval Street, a ...
From $478 per night (USD)Expedia
From $478 per night (USD)VRBO
Barracuda Bay Two Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Barracuda Bay! Just a mile from Key West International Airport, 3 miles from vibrant Duval Street, and ...
From $478 per night (USD)VRBO
From $313 per night (USD)Expedia
Mahi Mahi Manor Studio Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Mahi Mahi Manor! Ready for your getaway? Relax and refresh among the swaying palms. Our studio condo is ...
From $313 per night (USD)Expedia
From $304 per night (USD)VRBO
2BR suite | Pool | Hot Tub | Tennis | W/D
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites Dominican Suite 110 Escape to Key West and settle into a beautifully remodeled 2-bedroom, 2-bath condo a ...
From $304 per night (USD)VRBO
From $595 per night (USD)Expedia
The Cat's Meow - Truman Annex Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Cat’s Meow – your purrfect island vacation home! Whether your perfect Key West day means lingering on the ...
From $595 per night (USD)Expedia
From $325 per night (USD)VRBO
Key West Paradise Condo w/ Pool, Hot Tub, Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites Dominican Suite 110 Escape to Key West and settle into a beautifully remodeled 2-bedroom, 2-bath condo a ...
From $325 per night (USD)VRBO
From $318 per night (USD)Expedia
Tropical Key West Escape w/ Pool, Hot Tub, Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites Dominican Suite 110 Escape to Key West and settle into a beautifully remodeled 2-bedroom, 2-bath condo a ...
From $318 per night (USD)Expedia
From $630 per night (USD)VRBO
Classic Old Town Key West oasis, charming 3-bedroom in beautiful neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Experience the quintessential Key West lifestyle in this charming 3-bedroom home, nestled in one of Old Town’s most cove ...
From $630 per night (USD)VRBO
From $1080 per night (USD)Expedia
**PALMS ON DUVAL @ OLD TOWN** Home w/ Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $1080 per night (USD)Expedia
From $623 per night (USD)VRBO
Another Day in Paradise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Get ready to relax in this 3-bedroom townhome in Key West. This superb property boasts 2 queen beds, 1 king bed, and 1 f ...
From $623 per night (USD)VRBO
From $794 per night (USD)Expedia
**THE ELEGANT EGRET @ OLD TOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The perfect K ...
From $794 per night (USD)Expedia
From $1018 per night (USD)VRBO
Charming cottage with private hot tub - one block to Duvall Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Key West in style with this lovely vacation rental in the heart of Old Town! Up to six guests will enjoy a pr ...
From $1018 per night (USD)VRBO
From $1144 per night (USD)Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ease into the pleasures of a tropical vacation with this two bedroom, two bathroom condo in Key West. With a charming at ...
From $1144 per night (USD)Expedia
From $572 per night (USD)VRBO
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Soak up incredible west-facing views from the comfort of this elegant, dog-friendly Key West condo. First-rate amenities ...
From $572 per night (USD)VRBO
From $604 per night (USD)Expedia
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key ...
From $604 per night (USD)Expedia
From $2123 per night (USD)VRBO
Three Condos w/ Entertainment, Private Parking & Beach Nearby - Great for Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificin ...
From $2123 per night (USD)VRBO
From $503 per night (USD)Expedia
Cheery Beach Getaway Near Local Attractions - Pool & Easy Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. Wit ...
From $503 per night (USD)Expedia
From $462 per night (USD)VRBO
Colorful waterfront condo with pool & hot tub, AC, W/D, & WiFi - dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All the best of Key West is right at your doorstep at this colorful, second-floor condo just across the street from the ...
From $462 per night (USD)VRBO
From $307 per night (USD)Expedia
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we c ...
From $307 per night (USD)Expedia
From $708 per night (USD)VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and near ...
From $708 per night (USD)VRBO
From $842 per night (USD)Expedia
Comfortable Condo with Pool, Private Balcony, & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access t ...
From $842 per night (USD)Expedia
From $575 per night (USD)VRBO
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the very best of Key West living at this unique Old Town Truman Avenue Eyebrow home. Tucked away in a small, ...
From $575 per night (USD)VRBO
From $246 per night (USD)Expedia
Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexic ...
From $246 per night (USD)Expedia
From $482 per night (USD)VRBO
Enchanting Duplex with Private Pool, Central AC, WiFi, and Private Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Slip into a modern duplex with distinctly bright Key West vibes! One of the two properties to rent at the Tropical Vibes ...
From $482 per night (USD)VRBO
From $636 per night (USD)Expedia
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cot ...
From $636 per night (USD)Expedia
From $207 per night (USD)VRBO
Bright Duplex with Private Heated Pool, Central AC, WiFi, & Private Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a soak in your own private, heated saltwater pool at this lovely duplex! Part of the Tropical Vibes home, this dup ...
From $207 per night (USD)VRBO
From $281 per night (USD)Expedia
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a ...
From $281 per night (USD)Expedia
From $743 per night (USD)VRBO
Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sunset Suite -- Catalina Suite 311, your slice of paradise in vibrant Key West! This inviting two-bedroom con ...
From $743 per night (USD)VRBO
From $2033 per night (USD)Expedia
Historic Old Town home with three apartments, balcony, & lighthouse view
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher ...
From $2033 per night (USD)Expedia
From $708 per night (USD)VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Breathe the fresh ocean air and gaze upon tropical sunsets on your next trip to Key West with this one-bedroom, one-bath ...
From $708 per night (USD)VRBO
From $1261 per night (USD)Expedia
Spacious home with pool & balcony - 1 block from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large op ...
From $1261 per night (USD)Expedia
From $558 per night (USD)VRBO
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family do ...
From $558 per night (USD)VRBO
From $652 per night (USD)Expedia
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to your new getaway of choice on the Florida Keys! This two-bedroom and two-bathroom condo by Key West has it all ...
From $652 per night (USD)Expedia
From $257 per night (USD)VRBO
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whether it's the textured shiplap walls, the sparkling private saltwater pool, or the lovingly curated decor, you're sur ...
From $257 per night (USD)VRBO
From $345 per night (USD)Expedia
Bohemian island home full of color and modern amenities - in a great location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa De la Soul, a colorful and effortless island stay! From the moment you step in the front door, you will ...
From $345 per night (USD)Expedia
From $868 per night (USD)VRBO
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spend your vacation days snorkeling in the clear coastal waters and strolling the streets of downtown Key West when you ...
From $868 per night (USD)VRBO
From $186 per night (USD)Expedia
Charming island retreat with balcony, king bed, desk space & dog-friendly vibe
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Periwinkle Place—a bright, dog-friendly escape in the vibrant heart of Old Town Key West! Just one block from ...
From $186 per night (USD)Expedia
From $712 per night (USD)VRBO
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & ...
From $712 per night (USD)VRBO
From $621 per night (USD)Expedia
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the sunshine and soft sands of the Florida Keys with this amazing home in Sunrise Suites Resort in Key West wi ...
From $621 per night (USD)Expedia
From $677 per night (USD)VRBO
Studio with pool - 1 block to Duval St shops/restaurants & 2 blocks to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ideal for a small group or two couples traveling together and looking for a private, amenity-rich experience, this cozy ...
From $677 per night (USD)VRBO
From $636 per night (USD)Expedia
Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Dreaming about a tropical vacation? This two-bedroom, one-bathroom cottage in Key West is the perfect destination - a pr ...
From $636 per night (USD)Expedia
From $1747 per night (USD)VRBO
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a ...
From $1747 per night (USD)VRBO
From $677 per night (USD)Expedia
Tropical studio with pool - 2 blocks to beach & 1 block to Duval St dining/shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Plan your next getaway to this quaint tropical studio, complete with a well-equipped kitchenette, furnished patio, and a ...
From $677 per night (USD)Expedia
From $1076 per night (USD)VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bask in the tropics of Key West at this inviting cottage with a private heated pool and a lush backyard garden. This lo ...
From $1076 per night (USD)VRBO
From $1038 per night (USD)Expedia
Classic Key West cottage with pool & courtyard - walk to beach & Duval St dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Part of the Papa's Hideaway complex, this charming historic Key West cottage is an ideal home away from home for your ne ...
From $1038 per night (USD)Expedia
From $650 per night (USD)VRBO
Charming, colorful two-story apartment with two balconies - walk everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher ...
From $650 per night (USD)VRBO
From $421 per night (USD)Expedia
Cozy home with private pool, BBQ, central AC, enclosed yard
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise in this charming Key West house, offering a perfect blend of comfort and convenience. With a private ...
From $421 per night (USD)Expedia
From $260 per night (USD)VRBO
Dog-friendly condo near beach with pool, grill, outdoor shower, W/D, AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town and just two steps up to enter, this charming single-story cottage is the perfect setting for y ...
From $260 per night (USD)VRBO
From $280 per night (USD)Expedia
Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The ideal location of this super-comfortable corner property makes it the perfect blend of convenience, tranquility, and ...
From $280 per night (USD)Expedia
From $872 per night (USD)VRBO
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Comple ...
From $872 per night (USD)VRBO
From $800 per night (USD)Expedia
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next fami ...
From $800 per night (USD)Expedia
From $1456 per night (USD)VRBO
Charming dog-friendly home with guest cottage & private pool - great location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Slip into island time at Bahama House, a relaxed and inviting 3-bedroom, 3-bath retreat tucked away in the heart of Old ...
From $1456 per night (USD)VRBO
From $621 per night (USD)Expedia
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a ...
From $621 per night (USD)Expedia
From $650 per night (USD)VRBO
Charming, updated home near Duval St. with enclosed patio & walkable location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher ...
From $650 per night (USD)VRBO
From $153 per night (USD)Expedia
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and ...
From $153 per night (USD)Expedia
From $176 per night (USD)VRBO
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we c ...
From $176 per night (USD)VRBO
From $239 per night (USD)Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more ...
From $239 per night (USD)Expedia
From $2543 per night (USD)VRBO
The Southernmost Comfort House — Private Pool + Waterfall | 5BR Truman Annex Estate | 28-Day Stay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Southernmost Comfort House — 5BR/4BA Private Pool w/ Waterfall + Outdoor Shower + Detached 2-Car Garage | 28-Day Min ...
From $2543 per night (USD)VRBO
From $675 per night (USD)Expedia
Deluxe ground-floor studio - pool, courtyard, walk to Duval St shops & beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a tropical getaway to Key West at this adorable and colorful ground-floor studio, complete with a well-equipped ki ...
From $675 per night (USD)Expedia
From $178 per night (USD)VRBO
Tropical Cottage w/ Private Pool--Two blocks from Duval - Near Hemingway House!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Live Like a Local in the Heart of Key West! Welcome to your next luscious Vacay getaway—where history, culture, and isl ...
From $178 per night (USD)VRBO
From $986 per night (USD)Expedia
Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we c ...
From $986 per night (USD)Expedia
From $300 per night (USD)VRBO
One Bedroom Suite | Beachside Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind i ...
From $300 per night (USD)VRBO
From $227 per night (USD)Expedia
Signature Double at Beachside Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $227 per night (USD)Expedia
From $513 per night (USD)VRBO
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $513 per night (USD)VRBO
From $645 per night (USD)Expedia
Ocean Front Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $645 per night (USD)Expedia
From $525 per night (USD)VRBO
Pool View Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $525 per night (USD)VRBO
From $300 per night (USD)Expedia
Poolside Suite with Direct Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind i ...
From $300 per night (USD)Expedia
From $934 per night (USD)VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $934 per night (USD)VRBO
From $389 per night (USD)Expedia
Ocean Front Suite with Direct Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $389 per night (USD)Expedia
From $300 per night (USD)VRBO
Pool View Suite | Beachside Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind i ...
From $300 per night (USD)VRBO
From $845 per night (USD)Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $845 per night (USD)Expedia
From $218 per night (USD)VRBO
Signature King at Beachside Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $218 per night (USD)VRBO
From $338 per night (USD)Expedia
Ocean Front Suite | Beachside Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residen ...
From $338 per night (USD)Expedia
From $210 per night (USD)VRBO
Pool, Pet-friendly, Bicycles and 5 min walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Please note: This home requires a minimum stay of 28 nights or longer, as enforced by the HOA. No exceptions can be made ...
From $210 per night (USD)VRBO
From $226 per night (USD)Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a p ...
From $226 per night (USD)Expedia
From $157 per night (USD)VRBO
Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the best of Key West living! This classic cottage comes fully updated with modern amenities while boasting a ...
From $157 per night (USD)VRBO
From $816 per night (USD)Expedia
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Spend your next Key West vacation at this lovely condo in the Florida Keys. This rental comes equipped with a shared poo ...
From $816 per night (USD)Expedia
From $258 per night (USD)VRBO
Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
☀️ SNOWBIRD-FRIENDLY ISLAND ESCAPE - WALK TO DUVAL, BALCONY VIEWS, POOL & BEACH ACCESS! Welcome to your charming Key W ...
From $258 per night (USD)VRBO
From $597 per night (USD)Expedia
Fresh Getaway w/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we c ...
From $597 per night (USD)Expedia
From $274 per night (USD)VRBO
Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
An exceptional stay awaits at this three-bedroom, two-bath condo. Inside, the suite is open and inviting, with a large f ...
From $274 per night (USD)VRBO
From $1475 per night (USD)Expedia
Bright Key West House with Private Pool, Gas Grill, W/D, Central AC, & Free WiFi
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy modern Key West vibes with this home's bright accent colors, eye-catching tile work, and of course the sparkling p ...
From $1475 per night (USD)Expedia