Key West Rentals
From $1170 per night (USD)VRBO
THE 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 $1170 per night (USD)VRBO
From $588 per night (USD)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 ...
From $588 per night (USD)Expedia
From $723 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 $723 per night (USD)VRBO
From $1061 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 $1061 per night (USD)VRBO
From $254 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 $254 per night (USD)VRBO
From $1018 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 $1018 per night (USD)VRBO
From $278 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 $278 per night (USD)VRBO
From $197 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 $197 per night (USD)VRBO
From $256 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 $256 per night (USD)VRBO
From $281 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 $281 per night (USD)VRBO
From $184 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 $184 per night (USD)VRBO
From $1026 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 $1026 per night (USD)VRBO
From $513 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 $513 per night (USD)VRBO
From $272 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 $272 per night (USD)VRBO
From $168 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 $168 per night (USD)VRBO
From $254 per night (USD)Expedia
This is your Labor Day Week Getaway in Paradise ..... Coconut Mallory, Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This wonderful 2-bd condo has been our timeshare week for over 25 years. It is our home away from home; our chance to g ...
From $254 per night (USD)Expedia
From $224 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 $224 per night (USD)VRBO
From $286 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 $286 per night (USD)VRBO
From $330 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 $330 per night (USD)VRBO
From $272 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 $272 per night (USD)VRBO
From $651 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 $651 per night (USD)VRBO
From $647 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 $647 per night (USD)VRBO
From $1294 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 $1294 per night (USD)VRBO
From $336 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 $336 per night (USD)VRBO
From $224 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 $224 per night (USD)VRBO
From $286 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 $286 per night (USD)VRBO
From $237 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 $237 per night (USD)VRBO
From $340 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 $340 per night (USD)VRBO
From $817 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 $817 per night (USD)VRBO
From $262 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 $262 per night (USD)VRBO
From $325 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 $325 per night (USD)VRBO
From $1273 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 $1273 per night (USD)VRBO
From $311 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 $311 per night (USD)VRBO
From $422 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 $422 per night (USD)Expedia
From $286 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 $286 per night (USD)VRBO
From $133 per night (USD)Expedia
Sunny Island Escape | 1 bed, 1 bath monthly rental in heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the perfect island retreat in this beautifully updated one-bedroom, one-bath apartment located just steps from ...
From $133 per night (USD)Expedia
From $419 per night (USD)VRBO
LA PLUMA LOCA ~ Charming 3 BR/2Ba Home w/ Parking!
- 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 $419 per night (USD)VRBO
From $660 per night (USD)VRBO
Paradise Found, unique 2BR home with Private Heated pool, off-street private parking!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful architect designed home from the 1990's in the process of being lovingly restored and redecorated. This is a ...
From $660 per night (USD)VRBO
From $383 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 $383 per night (USD)VRBO
From $336 per night (USD)Expedia
Charming 2-bedroom house with AC, WiFi in cool Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Consider this house your home away from home while you visit Key West. This wonderful property features 2 queen bedrooms ...
From $336 per night (USD)Expedia
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 $587 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 $587 per night (USD)VRBO
From $538 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 $538 per night (USD)VRBO
From $135 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 $135 per night (USD)VRBO
From $155 per night (USD)VRBO
Charming 1-bedroom apartment in Key West with AC, WiFi. Enjoy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Key West at this brilliant apartment. This marvelous space features 1 bedroom with a queen b ...
From $155 per night (USD)VRBO
From $1826 per night (USD)VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1826 per night (USD)VRBO
From $1824 per night (USD)VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1824 per night (USD)VRBO
From $177 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 $177 per night (USD)VRBO
From $253 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 $253 per night (USD)VRBO
From $1771 per night (USD)VRBO
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $1771 per night (USD)VRBO
From $2236 per night (USD)VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
From $1759 per night (USD)VRBO
Parrot Key | Beachfront | Kitchen | Hot Tub | Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a paradise of white sands and glimmering pools, where boat drinks and watersports are just steps away at Parro ...
From $1759 per night (USD)VRBO
From $1941 per night (USD)VRBO
The Banyan | Concierge | Beach Access | Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1941 per night (USD)VRBO
From $1759 per night (USD)VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)VRBO
From $1759 per night (USD)VRBO
Coconut Beach | Beach | Concierge | Pool | Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)VRBO
From $2148 per night (USD)VRBO
Hyatt Beach | Concierge | Spa | Pool | Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $2148 per night (USD)VRBO
From $1839 per night (USD)VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $1839 per night (USD)VRBO
From $11524 per night (USD)VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $11524 per night (USD)VRBO
From $2236 per night (USD)VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
From $1733 per night (USD)VRBO
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $1733 per night (USD)VRBO
From $968 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 $968 per night (USD)VRBO
From $812 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 $812 per night (USD)VRBO
From $987 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 $987 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Florida Charming 1-bedroom resort with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your private sanctuary in the lush landscape of Key West. Imagine old-fashioned screen-enclosed porches, gard ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $263 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 $263 per night (USD)VRBO
From $1231 per night (USD)VRBO
MERMAID COVE - A collection of four units on Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decora ...
From $1231 per night (USD)VRBO
From $537 per night (USD)Expedia
THALIA'S RETREAT @ Duval Square 2bd/2ba townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
From $537 per night (USD)Expedia
From $1214 per night (USD)VRBO
No secrets at Pilar's Secret - Just a great location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1214 per night (USD)VRBO
From $311 per night (USD)VRBO
Deckside Suite - Efficiency at its finest!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get ...
From $311 per night (USD)VRBO
From $1062 per night (USD)VRBO
Windsor Townhomes #6 - Large pool 3B/3.5 bath, 3 blocks to Duval
- 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 $1062 per night (USD)VRBO
From $326 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 $326 per night (USD)Expedia
From $392 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 $392 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 $513 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 $513 per night (USD)VRBO
From $526 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 $526 per night (USD)VRBO
From $1012 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 $1012 per night (USD)VRBO
From $338 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 $338 per night (USD)VRBO
From $1040 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 $1040 per night (USD)VRBO
From $179 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 $179 per night (USD)VRBO
From $378 per night (USD)VRBO
ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This newly remodeled Conch house is located on Olivia Street in Old Town Key West just two and a half blocks from World ...
From $378 per night (USD)VRBO
From $416 per night (USD)Expedia
Escape to the wonderful Cuban Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon bec ...
From $416 per night (USD)Expedia
From $645 per night (USD)VRBO
Tropical Village: The Southern Cross - Quiet & gated. Pool/Porch/Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
There are stars in the southern sky! The Southern Cross takes its name from the “crux” constellation that guided sailors ...
From $645 per night (USD)VRBO
From $1578 per night (USD)Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1578 per night (USD)Expedia
From $1153 per night (USD)VRBO
A contemporary island gem that was formerly used as a bottling plant,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable t ...
From $1153 per night (USD)VRBO
From $367 per night (USD)VRBO
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Hideout, where luxury meets location. Look no further than "The Hideout" for upscale luxury and single- ...
From $367 per night (USD)VRBO
From $441 per night (USD)VRBO
Key West at Ocean’s Corner!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Whether you want to explore the historic sites, enjoy the nightlife, or relax in nature, you’ll find it all during your ...
From $441 per night (USD)VRBO
From $354 per night (USD)VRBO
Escape to \"Oasis on 18th\" w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...
From $354 per night (USD)VRBO
From $404 per night (USD)VRBO
Last Mango Beach Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the allure of La Brisa Penthouse! Step into this captivating two-bedroom, two-bathroom condo nestled within t ...
From $404 per night (USD)VRBO
From $588 per night (USD)VRBO
Beach Club #112 - Unique Oceanfront living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $588 per night (USD)VRBO
From $382 per night (USD)VRBO
Escape to \"Casa Escondida\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $382 per night (USD)VRBO
From $3478 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $3478 per night (USD)VRBO
From $1189 per night (USD)VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1189 per night (USD)VRBO
From $1705 per night (USD)VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1705 per night (USD)VRBO
From $354 per night (USD)VRBO
SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $354 per night (USD)VRBO
From $472 per night (USD)Expedia
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $472 per night (USD)Expedia
From $471 per night (USD)VRBO
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $471 per night (USD)VRBO
From $373 per night (USD)VRBO
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Bose speaker, Alexa Echo, full kitche ...
From $373 per night (USD)VRBO