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From $255 per night (USD)
VRBO
Seaport Serenity Cottage - Quiet and Quaint
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2BR/2BA rental is located in the Historic Seaport District offering off-street parking and a prime locatio ...
From $255 per night (USD)
VRBO
From $465 per night (USD)
Expedia
Rooster Doodle Do - Midtown Family Retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Your perfect tropical getaway! This stunning 3-bedroom, 3-bathroom home with an additional guest cottage is designed for ...
From $465 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Charming 1923 2 Bedroom, 1 Bath home with bonus loft.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to The Emma House! A delightful 1923 Key West retreat located in the heart of historic and vibrant Bahama Villa ...
From $220 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Beachfront Condo in heart of Key West, minutes to downtown 1BR-1BA 2 lg pools 🚲
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Key West-Resort style living! Spacious 1 bed/ 1 bath, large living space full-kitchen condo in gated community. Beachf ...
From $219 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbe ...
From $559 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Jerry's Escape - Truman @ Duval | Cozy Studio Perfect for Couples
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval - Unit C | Cozy Studio Perfect for Couples Experience your perfect romantic retreat, offering a charming ...
From $315 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime Location Welcome to your perfect family getaway in the ...
From $357 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Ricky's Retreat - Truman @ Duval | Perfect for a Getaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval Unit A | Perfect for a Getaway in Key West Escape to this cozy, vibrant cottage in the heart of downtown ...
From $430 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Scott's Cottage - Truman @ Duval F | Perfect Location! Ideal for Solos & Couples Looking for a relaxing retreat in the ...
From $425 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval - Unit E | Cozy Getaway in the Heart of Key West Duval Studio is your perfect launchpad for an unforgett ...
From $409 per night (USD)
Expedia
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VRBO
Key West 2 BR Villa with full kitchen, ocean view with Infinity pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Key West just minutes from beautiful sunsets at Mallory Square or renowned dining and nightlife of Duval Stre ...
Click For Pricing
VRBO
From $312 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stylish, pet-friendly, and amazing decor is what awaits you. This boutique hotel offers you a great stay in the heart of ...
From $312 per night (USD)
VRBO
From $407 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 420 sq. ft, equipped with complimentary toiletries, standard ...
From $407 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Charming Hideaway with Pool Access – Walk to Duval St! Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $695 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Sunny Florida Escape with Pool, Beach Access & Stunning Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $550 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Cozy Key West Escape – Near Shops, Bars & Famous Duval Street! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $482 per night (USD)
VRBO
From $465 per night (USD)
VRBO
CASA DEL SUR ~ Renovated 2 BR/2Ba Home with Heated Dip Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
QUAINT AND PRIVATE HIDEAWAY... This Key West classic checks all the boxes for your blissful getaway to our tiny island p ...
From $465 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Cozy & modern guest house in Key West with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Your cozy getaway awaits in Key West at this marvelous apartment. With a bedroom, washing & drying machine, AC, and WiFi ...
From $193 per night (USD)
Expedia
From $441 per night (USD)
VRBO
Royal Palm of Casa Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
EXQUISIT NEW CONSTRUCTION HOME!!!! Discover the epitome of modern luxury and comfort at this brand-new exquisite 4-bedr ...
From $441 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Pet-Friendly & Cozy Bungalow, Daily Breakfast & Poolside Lounging!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $446 per night (USD)
VRBO
From $433 per night (USD)
VRBO
Bungalow in Heart of Key West | 3 Pool, Free Breakfast, Shops & Bars Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $433 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Key West Charm | 3 Pools, Complimentary Breakfast, Near Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $479 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Key West Getaway | Romantic Bungalow, Pools, Free Breakfast & Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $528 per night (USD)
VRBO
From $465 per night (USD)
Expedia
Cozy Home in Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home in beautiful Key West! This cozy and comfortable 3-bedroom retreat is nestled on a d ...
From $465 per night (USD)
Expedia
From $1649 per night (USD)
VRBO
The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Penthouse at Custom House Inn | Serene Coastal Escape on Duval Street! Immerse yourself in the calm and comfort of ...
From $1649 per night (USD)
VRBO
Click For Pricing
Expedia
Most Beautiful View on Key West?
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Make yourself at home in this 2-bedroom Key West retreat. This cool condo features a beautiful view from every room. Spa ...
Click For Pricing
Expedia
From $2218 per night (USD)
VRBO
Charmayne’s Cottages | Your Private Group Oasis in the Heart of Key West
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Charmayne’s Cottages | Your Private Group Oasis in the Heart of Key West Experience the ultimate Key West getaway at Ch ...
From $2218 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Key West Comfort | Bungalow with Patio, 3 Pools! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $439 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Central Key West Stay | 3 Pools, Free Daily Breakfast, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Tropical Bungalow, 3 Pools, Breakfast Included, Pets Allowed, Near Shops & Bars
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $458 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Charming island retreat with balcony, king bed, desk space & dog-friendly vibe
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Periwinkle Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $218 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Quiet 2-bedroom plus office townhome on the Key West golf course!
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Just a short walk from the Resort style pool and fitness center, our townhome, situated on the 1st fairway of the Key We ...
From $168 per night (USD)
VRBO
From $599 per night (USD)
VRBO
Upscale 2-bdrm Lock-off villa in the heart of Old Town. Close to Mallory Square
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this upscale condo in Key West. This terrific property features a one-bedroom villa with plush queen bed, ful ...
From $599 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Charming island cottage with sunny patio, modern kitchen, AC & dog friendly yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Casa Sirena Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $454 per night (USD)
Expedia
From $359 per night (USD)
VRBO
COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Cocktails on the Corner — Your Tropical Oasis in Old Town Key West! Step into the perfect blend of historic ...
From $359 per night (USD)
VRBO
From $835 per night (USD)
Expedia
Sandbar Suite | 2 bed/2 bath apartment with patio overlooking Front Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Sandbar Suite – 2BR/2BA Island Getaway with Front Street views Welcome to The Sandbar Suite, a bright and breezy 2 ...
From $835 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Key Lime Hideaway- Traditional Key West Style House in Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Your Old Key West Oasis! Experience the charm of Old Key West in this stunning traditional Conch-style home. ...
From $330 per night (USD)
VRBO
From $332 per night (USD)
Expedia
A Sunset Celebration at the Key West Golf Club - Photos Coming Soon!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This lovely, fully furnished, townhouse has three bedrooms that sleeps up to 6 and two full baths . The spacious upstair ...
From $332 per night (USD)
Expedia
From $1327 per night (USD)
VRBO
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
GRAND OPENING SUMMER DEALS FOR VINTAGE SOUTHERNMOST COTTAGE... Envision sun soaked days under luxuriant balmy breezes in ...
From $1327 per night (USD)
VRBO
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Expedia
KEY WEST- Amazing 3 rd floor corner unit overlooking Florida Bay and Yacht Club.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Consider this 3rd floor corner condo overlooking the Florida Bay and Yacht Club as your next vacation destination. Enjoy ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Your 2025 Labor Day Week Getaway in Paradise ..... Coconut Mallory, Key West.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a ONE-WEEK opportunity to enjoy Paradise! Our week can be yours in September 2025. This wonderful 2-bd con ...
Click For Pricing
VRBO
From $886 per night (USD)
VRBO
Kick Back in 3 Pool-View Rooms at Key West’s Blue Flamingo Resort
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $886 per night (USD)
VRBO
From $1181 per night (USD)
VRBO
4 Pool-view Rooms with 2 Queen Beds l Island Vibes Await in Blue Flamingo Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Key West’s newest island escape offers breezy rooms, poolside cabanas, and nonstop fun. Lounge by the pool, enjoy tiki c ...
From $1181 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Colorful Stay at Blue Flamingo | Poolside Bar, Lawn Games, Music & Fire Pits
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Perched at the gateway to Key West, Blue Flamingo Resort immerses guests in island vibes with tiki cocktails, poolside c ...
From $270 per night (USD)
VRBO
From $982 per night (USD)
VRBO
Group Getaway in 3 Ocean-View Rooms | Blue Flamingo Resort Key West with Pools
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $982 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Chill & Play in Key West | Pools, Tiki Bar, Games, Fire Pits & Island Eats
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience luxury and space in this studio suite at Blue Flamingo Resort, offering uninterrupted ocean vistas. The suite ...
From $334 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Sun, Sip, & Socialize | Island Stay w/ 2 Pools & Backyard Bash
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located at the entrance to Key West, Blue Flamingo Resort offers a tropical escape with easy access to Duval Street, Mal ...
From $237 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Family-Friendly Two Queen Beds Room Near Key West Hotspots
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $327 per night (USD)
VRBO
From $287 per night (USD)
VRBO
All-Day Fun in Key West |Lawn Games, Pools & Cabanas, Karaoke Fun, Free Shuttle
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the lively atmosphere of Blue Flamingo Resort, complete with poolside bars and daily entertainment. This room ...
From $287 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Spacious Double Queen Room with Contemporary Touches
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $328 per night (USD)
VRBO
From $1376 per night (USD)
VRBO
Blue Flamingo Resort l 4 Rooms, Pool, Cabanas, Karaoke & Old Town Shuttle
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $1376 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Three Rooms w/ 2 Queen beds at Blue Flamingo Resort Key West l 2 Pools & Shuttle
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay at Blue Flamingo Resort Key West, featuring comfortable two queen beds and convenient access to South Roosevelt Bou ...
From $658 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Sun, Sip, & Socialize | Island Stay with 2 Pools & Lawn Games
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Situated on a higher floor, this room at Blue Flamingo Resort offers panoramic views of Key West's charming landscape. F ...
From $320 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Tropical Playground | Relaxed Key West Stay w/ Pool, Karaoke Nights & Tiki Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Perched at the gateway to Key West, Blue Flamingo Resort immerses guests in island vibes with tiki cocktails, poolside c ...
From $270 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Key West Poolside Paradise w/ Cabanas, Lawn Games & Tiki Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $296 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Island Charm & Retro Fun | Pools, Comfort Eats, Shuttle & Fire Pits
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the tropical ambiance of Blue Flamingo Resort, featuring lush gardens and vibrant poolside activities. This room p ...
From $296 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Poolside Paradise in Key West | Renovated Room, 2 Pools, Games & Live Music
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Blue Flamingo Resort's oceanfront location offers guests breathtaking sea views and easy beach access. This room feature ...
From $316 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Live the Island Life | Pool, Lawn Games, Cabanas & Karaoke Nights
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience luxury and space in this studio suite at Blue Flamingo Resort, offering uninterrupted ocean vistas. The suite ...
From $334 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Poolside Paradise l Fire Pits, Lawn Games, Live Music & Endless Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $316 per night (USD)
VRBO
From $982 per night (USD)
VRBO
Three Rooms w/ 2 Queen beds at Blue Flamingo Resort Key West l 2 Pools & Shuttle
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Blue Flamingo Resort offers a vibrant stay at Key West's entrance, with easy access to beaches, dining, and entertainmen ...
From $982 per night (USD)
VRBO
From $632 per night (USD)
VRBO
Where Fun Meets Chill | 2 Island View Rooms in Blue Flamingo Resort Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $632 per night (USD)
VRBO
From $1264 per night (USD)
VRBO
Island Views & Comfort | 4 Rooms at Blue Flamingo Key West l Pools & Cabanas
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $1264 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Carefree Key West Days | 2 Pools, Karaoke Nights, Tiki Drinks & Games
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in the ultimate Key West experience in this one-bedroom suite at Blue Flamingo Resort, boasting direct ocean vie ...
From $424 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Colorful Key West Escape | Pools, Food Trucks, Karaoke Night & Free Shuttle
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located at the entrance to Key West, Blue Flamingo Resort offers a tropical escape with easy access to Duval Street, Mal ...
From $237 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Laid-Back Luxe | Pools, Comfort Foods, Lawn Games & Shuttle to Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $327 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Key West Fun Zone: Pools, Lawn Games, Fire Pits, Tiki Cocktails & More
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the lively atmosphere of Blue Flamingo Resort, complete with poolside bars and daily entertainment. This room ...
From $286 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Relax & Have Fun | Key West Poolside Stay w/ Pools, Games & Comfort Eats
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $327 per night (USD)
VRBO
From $948 per night (USD)
VRBO
Blue Flamingo Key West | Three Island View Rooms w/ 2 Queen Beds
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Perched above the vibrant streets of Key West, this room provides sweeping island vistas. With two queen beds and contem ...
From $948 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Key West Resort Room | Fun Dining, Pools, Music Nights & Free Shuttle to Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Blue Flamingo Resort's oceanfront location offers guests breathtaking sea views and easy beach access. This room feature ...
From $316 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Breezy Key West Stay | Renovated Rooms, Pool, Bar & Nightly Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the vibrant energy of Blue Flamingo Resort from this one-bedroom suite overlooking the pool. Featuring a separate ...
From $410 per night (USD)
VRBO
From $1310 per night (USD)
VRBO
Group Getaway in 3 Ocean-View Rooms | Blue Flamingo Resort Key West with Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Wake up to the soothing sounds of the ocean in this spacious room at Blue Flamingo Resort. With two queen beds and panor ...
From $1310 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Casa Mamisa - 2 bedroom home in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The two bedroom Casa Mamisa is your home away from home on a quiet lane just off of Duval Street. This peaceful space fe ...
From $371 per night (USD)
Expedia
From $376 per night (USD)
VRBO
LONE PALM COTTAGE ~ 3 BR, 2 Ba Home w/ 2 Cottages, Pool & Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OLD TOWN AMBIENCE.... This home with 2 mini cottages captures the essence of time-honored Key West living from the mome ...
From $376 per night (USD)
VRBO
From $561 per night (USD)
Expedia
Coral Reef Suite | 1 bed, 1 bath monthly rental near Key West's historic waterfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the Heart of Key West from This Charming Monthly Vacation Retreat! Stay just steps from the action in this b ...
From $561 per night (USD)
Expedia
From $218 per night (USD)
VRBO
LA PLUMA LOCA ~ Charming and Updated 3 Bedroom, 2 Bath Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
COZY ISLAND HIDEAWAY… Enter this heavenly slice of southernmost charm, located in the heart of Old Town. The enchanting ...
From $218 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Margaretaville in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 2 bath home instantly transports you into the Key West lifestyle with its living space, balcony, and dec ...
From $222 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Secluded Gardens Key West Condo - Pool, Balconies & Off‑Street Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Secluded Gardens in Old Town Key West – with Pool, 2 Balconies, and Off‑Street Parking. Why you’ll love it: - Two priv ...
From $336 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Hyatt Windward Pointe, Key West 2-Bdrm Condo Oct 23-26, 2025 Fantasy Fest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Celebrate Fantasy Fest in beautiful Key West. Enjoy the last full weekend of Fantasy Fest in this 2 bedroom condo that ...
From $478 per night (USD)
Expedia
From $1295 per night (USD)
VRBO
Poolside Paradise-Pvt. pool/spa, Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful architect designed home from the 1990`s in the process of being lovingly restored and redecorated. This is a ...
From $1295 per night (USD)
VRBO
$Savor \Margarita on Margaret\ w/ PRIVATE Pool$
From $546 per night (USD)
VRBO
Savor \"Margarita on Margaret\" w/ PRIVATE Pool
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Savor the Key West Lifestyle at "Margarita on Margaret" - Private All Oasis. Escape to your own private slice of paradis ...
From $546 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Superb waterfront Coconut Mallory 2 BR, 2 bath condo, 2 pools, incredible views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
No matter where you stay on the Key West island, you'll be able to get to whatever historical site, beach, restaurant, b ...
From $400 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Oceanfront 2-bedroom Villa at a Resort in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This memorable resort is the perfect home base for your trip to Key West. With 2 bedrooms and 2 bathrooms featuring a je ...
From $315 per night (USD)
VRBO
From $611 per night (USD)
VRBO
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman Annex Welcome to your sunny esc ...
From $611 per night (USD)
VRBO
From $728 per night (USD)
VRBO
Serenity by the Sea, 2BR/2BA Condo w/Pool at La Brisa across from Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serenity by the Sea | 2BR/2BA Key West Condo at La Brisa Welcome to your tropical retreat in paradise! This beautifully ...
From $728 per night (USD)
VRBO
From $142 per night (USD)
VRBO
Charming Cottage in Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your Key West adventure begins at this charming 1-bedroom cottage. The lovely bedroom features a comfortable queen bed, ...
From $142 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Step into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the cov ...
From $230 per night (USD)
VRBO
From $370 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $370 per night (USD)
VRBO
From $251 per night (USD)
Expedia
3 Bedroom 2 Bathroom Near Beaches and Art Galleries
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Spacious 3-Bedroom, 2-Bathroom Retreat in Key West Escape to paradise in this charming Key West rental, perfectly situa ...
From $251 per night (USD)
Expedia
From $1091 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional $ ...
From $1091 per night (USD)
VRBO
From $972 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $972 per night (USD)
VRBO
From $354 per night (USD)
VRBO
Helluva Happy Place | Escape to Old Town Key West - 3 bed/2.5 bath townhome with private pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled i ...
From $354 per night (USD)
VRBO
From $732 per night (USD)
VRBO
Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2/2 townhome -
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. Ther ...
From $732 per night (USD)
VRBO
From $1053 per night (USD)
VRBO
Relax in Style at Windsor Townhomes #4
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1053 per night (USD)
VRBO
From $641 per night (USD)
VRBO
Oceanfront Splendor @ the Key West Beach Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets. Enjoy endless views of the tranquil waters of ...
From $641 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Half block to Duval @ Mango Hideaway -studio apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Mango Hideaway is comfortable junior suite, with sofa sitting area with adjoining king bedroom. The suite features ...
From $514 per night (USD)
VRBO
From $439 per night (USD)
VRBO
ALOHA - Large 1 level 4bd/4ba Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Aloha is a stunning private residence on corner lot in the Casa Marina District. Updated 2 years ago, this beautiful hom ...
From $439 per night (USD)
VRBO
From $724 per night (USD)
VRBO
Eyebrow Suite - 2bd/1.5ba Suite off Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and pa ...
From $724 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Rent at PORCHSIDE PARADISE - Steps to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
From $385 per night (USD)
Expedia
From $1425 per night (USD)
VRBO
Spacious Townhome on Windsor Lane 3/3.5
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1425 per night (USD)
VRBO
From $332 per night (USD)
VRBO
ESPERANZA SUITE Monthly Rental close to Duval
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Esperanza Suite is a bi-level suite with a very spacious upstairs king bedroom with a writing desk and chair and a color ...
From $332 per night (USD)
VRBO

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