Florida Keys National Marine Sanctuary Rentals
From $595 per night (USD)VRBO
Hyatt Vacation Club at Windward Pointe Resort. 2 Bedroom/2 Bath Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax in a tropical retreat overlooking the Atlantic Ocean, Windward Pointe captures the essence of Key West. The resort ...
From $595 per night (USD)VRBO
From $344 per night (USD)Expedia
Florida Keys Bayside with Beautiful Sunset Water Access and View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the Florida Keys with so many offerings at this one of a kind 3 Bedroom 3 Bathroom house in a private gated commu ...
From $344 per night (USD)Expedia
From $418 per night (USD)VRBO
Charming 2-bedroom home close to Sombrero Beach in fantastic Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Canalfront Retreat Near Sombrero Beach – 2 Bed / 2 Bath Escape to paradise at this beautifully appointed 2-bed ...
From $418 per night (USD)VRBO
From $309 per night (USD)Expedia
Last min discount Aug PARK PLACE, Waterfront, dock, golf cart, bike, Paddleboard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Get ready to relax in this spacious and serene 2-bedroom waterfront resort villa in Cudjoe Key. Our exquisitely design ...
From $309 per night (USD)Expedia
From $683 per night (USD)VRBO
Keys Launchpad: 5 BR, 4 BA House in Marathon, Sleeps 12
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Keys Launchpad, a stunning new-construction vacation home located in the exclusive Emerald Flats community in ...
From $683 per night (USD)VRBO
From $320 per night (USD)Expedia
Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets 🌅 Escape to your own tropical retreat ...
From $320 per night (USD)Expedia
From $232 per night (USD)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 ...
From $232 per night (USD)VRBO
From $198 per night (USD)VRBO
Ocean Bliss on Beach Heated Pool & Views Unit 32
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About this space Wake up to palm trees and the sound of waves. Lounge by the heated pool, stroll to your private beach, ...
From $198 per night (USD)VRBO
From $641 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 $641 per night (USD)VRBO
From $854 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 $854 per night (USD)VRBO
From $186 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 $186 per night (USD)VRBO
From $738 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 $738 per night (USD)VRBO
From $277 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 $277 per night (USD)VRBO
From $440 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 $440 per night (USD)VRBO
From $198 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 $198 per night (USD)VRBO
From $206 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 $206 per night (USD)VRBO
From $198 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 $198 per night (USD)VRBO
From $778 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 $778 per night (USD)VRBO
From $395 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 $395 per night (USD)VRBO
From $245 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 $245 per night (USD)VRBO
From $186 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 $186 per night (USD)VRBO
From $620 per night (USD)Expedia
Charming 3-bedroom villa with WiFi, AC in welcoming Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience Marathon like a local in this 3-bedroom villa. This amazing property features 1 king bed and 1 queen bed, per ...
From $620 per night (USD)Expedia
From $334 per night (USD)VRBO
Cabana Club, Kayaks, Pets, Boat Dock, Near Golf!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Latitude Adjustment – Your Slice of Paradise in Key Colony Beach! Escape to Latitude Adjustment, a beautifull ...
From $334 per night (USD)VRBO
From $214 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 $214 per night (USD)VRBO
From $214 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 $214 per night (USD)VRBO
From $277 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 $277 per night (USD)VRBO
From $236 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 $236 per night (USD)VRBO
From $591 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 $591 per night (USD)VRBO
From $471 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 $471 per night (USD)VRBO
From $943 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 $943 per night (USD)VRBO
From $332 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 $332 per night (USD)VRBO
From $440 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 $440 per night (USD)VRBO
From $246 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 $246 per night (USD)VRBO
From $206 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 $206 per night (USD)VRBO
From $246 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 $246 per night (USD)VRBO
From $708 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 $708 per night (USD)VRBO
From $228 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 $228 per night (USD)VRBO
From $290 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 $290 per night (USD)VRBO
From $983 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 $983 per night (USD)VRBO
From $884 per night (USD)Expedia
Grand Admiral - 46’ 2 Cabin Yacht
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome aboard your private floating hotel room, docked at The Perry Hotel & Marina in Key West. This lovely vessel feat ...
From $884 per night (USD)Expedia
From $228 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 $228 per night (USD)VRBO
From $193 per night (USD)Expedia
Cousy House in Key Largo with a Private Boat Ramp and Beach access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to paradise at our charming 2-bedroom, 1-bathroom Florida Keys vacation house, the perfect setting for an unforge ...
From $193 per night (USD)Expedia
From $371 per night (USD)VRBO
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)VRBO
From $429 per night (USD)Expedia
Private Florida Keys Escape w/ Pool, Dock, Tiki Bar – Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Little Torch Treasure – Private Pool, Tiki Bar, Dock, and More in the Florida Keys Welcome to Little Torch Treasure, you ...
From $429 per night (USD)Expedia
From $251 per night (USD)VRBO
Tranquil canal home w/ paddleboards, kayaks, & dock rental option
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Lookout at Lorelane Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $251 per night (USD)VRBO
From $397 per night (USD)Expedia
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 $397 per night (USD)Expedia
From $292 per night (USD)VRBO
Key Largo 2-bedroom apartment with WiFi-Pool-Tiki-Pet Friendly 5lbs or less
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to relax in this 2-bedroom apartment in Key Largo in Mile Marker 99. This brilliant space features 2 king beds ...
From $292 per night (USD)VRBO
From $433 per night (USD)Expedia
146 RV & 138 RV Vacation Rental n Key Largo Kampground, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
RV 146 RV has Kitchen with new stove/oven, kitchen utensils, Keurig coffee maker, rice cooker, toaster, etc. Sleeps 4 ...
From $433 per night (USD)Expedia
From $313 per night (USD)VRBO
138 RV Vacation Rental in Key Largo Kampground, FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
About this space RV has Kitchen with new stove/oven, kitchen utensils, Keurig coffee maker, rice cooker, toaster, etc. S ...
From $313 per night (USD)VRBO
From $334 per night (USD)Expedia
Oceanfront 2BR/2BA Remodeled Condo King + Bunk Room Balcony Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your oceanfront sanctuary! Unit 1314 has been completely remodeled from top to bottom—featuring modern finish ...
From $334 per night (USD)Expedia
From $281 per night (USD)VRBO
Enchanting Island Escape with water views, Large House in Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this cozy waterfront paradise, complete with boat docks and breathtaking sunset views. This inviting home off ...
From $281 per night (USD)VRBO
From $262 per night (USD)Expedia
Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Wake up to panoramic views of the sparkling marina and the endless ocean from this beautifully appointed 2-bedr ...
From $262 per night (USD)Expedia
From $1091 per night (USD)VRBO
Deactivated due to Bad Review and Low Productivity compared to other listings.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1091 per night (USD)VRBO
From $145 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 $145 per night (USD)Expedia
From $558 per night (USD)VRBO
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience waterfront FL Keys living at its finest at The Seascape, a modern, newly constructed retreat nestled directly ...
From $558 per night (USD)VRBO
From $228 per night (USD)Expedia
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 $228 per night (USD)Expedia
From $264 per night (USD)VRBO
Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Pirate’s Paradise – your ideal tropical escape in the Lower Keys! This 3-bedroom canal front home on Cudjoe ...
From $264 per night (USD)VRBO
From $590 per night (USD)Expedia
Off The Charts-Waterfront Tiki Bar & Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been ...
From $590 per night (USD)Expedia
From $183 per night (USD)VRBO
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 $183 per night (USD)VRBO
From $287 per night (USD)Expedia
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 $287 per night (USD)Expedia
From $413 per night (USD)VRBO
Newly Renovated 4BR/3BA Home in Marathon with Private Pool, Jetted Tub, and 40' Canal Dockage
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Nestled along a tranquil canal in Marathon, this newly renovated 4-bedroom, 3-bathroom retreat offers an elegant escape ...
From $413 per night (USD)VRBO
From $541 per night (USD)Expedia
FREE TIME 50’ 2 Cabin Yacht Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All aboard your 50-foot luxury motor yacht in stunning Key West—your adventure starts here! Experience the best of life ...
From $541 per night (USD)Expedia
From $1070 per night (USD)VRBO
Modern Sea Ray Yacht 1BR + Convertible Salon Bed and 2Bath ~ Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience Key West from the water in elevated style aboard this 46’ Sea Ray—your floating luxury suite docked at one of ...
From $1070 per night (USD)VRBO
From $291 per night (USD)Expedia
Spacious 4-bedroom house with large family and dining room. BRAND NEW
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Stock Island, brand new 4-bedroom house. This delightful property features WiFi, washer/dryer, upgraded appl ...
From $291 per night (USD)Expedia
From $210 per night (USD)VRBO
3-bedroom mobile home in amazing Key Largo with AC, WiFi and a private boat ramp
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Your peaceful retreat in Key Largo with 3 bedrooms awaits. This welcoming mobile home features 2 king beds and 1 bunk be ...
From $210 per night (USD)VRBO
From $241 per night (USD)VRBO
Treasure Hideaway: Your Private Paradise in the Florida Keys!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Treasure Hideaway – Your Private Oasis in the Florida Keys! Nestled in the heart of Marathon, Treasure Hidea ...
From $241 per night (USD)VRBO
From $352 per night (USD)VRBO
Waterfront home with private dock, canal views, large terrace & modern kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
La Isla Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $352 per night (USD)VRBO
From $474 per night (USD)Expedia
Keys Cottage with Beach and Dockage! Bayfront Property!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Deckhouse" is the perfect beachy cottage for your Keys vacation! It has a full-size kitchen with granite countertops an ...
From $474 per night (USD)Expedia
From $196 per night (USD)VRBO
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
water front home is located on 100 foot wide canal with your own 30 feet of Free dockage. We are pet friendly. Furnished ...
From $196 per night (USD)VRBO
From $446 per night (USD)Expedia
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Fam ...
From $446 per night (USD)Expedia
From $301 per night (USD)VRBO
Sumptuous Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $301 per night (USD)VRBO
From $368 per night (USD)Expedia
W04 - 209 Sombrero Beach Rd.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newer built canal front townhouse in the Anglers area of the Sombrero Beach neighborhood. This home features a private h ...
From $368 per night (USD)Expedia
From $470 per night (USD)VRBO
Waterfront Cottage - Beach and Dockage! Open Water Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In a world of chain hotels and paved over paradise, experience the Florida Keys the way they used to be! Sitting on a pr ...
From $470 per night (USD)VRBO
From $478 per night (USD)Expedia
\"Your own private resort\" - Mockingbird Pointe - Waterfront, pool and dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with priva ...
From $478 per night (USD)Expedia
From $427 per night (USD)VRBO
Nader's Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
From $427 per night (USD)VRBO
From $292 per night (USD)Expedia
P64 - Spacious 3 bedroom duplex in Key Colony with dockage and Cabana Club...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $292 per night (USD)Expedia
From $282 per night (USD)VRBO
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and bea ...
From $282 per night (USD)VRBO
From $266 per night (USD)Expedia
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $266 per night (USD)Expedia
From $540 per night (USD)VRBO
A Taste of Vitamin Sea
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
STR21-000361Your vacation awaits at A Taste of Vitamin Sea in desirable Key Colony Beach! Vitamin Sea's canal frontage b ...
From $540 per night (USD)VRBO
From $528 per night (USD)Expedia
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $528 per night (USD)Expedia
From $566 per night (USD)VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $566 per night (USD)VRBO
From $541 per night (USD)Expedia
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $541 per night (USD)Expedia
From $497 per night (USD)VRBO
Luxury 3BR/3BA Cottage with the Best Sunset Views in the Florida Keys!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Professionally decorated, fully renovated Cottage with 3 Bedrooms & 3 Bathroom Cottage located in the Village at Hawks ...
From $497 per night (USD)VRBO
From $880 per night (USD)Expedia
Elegant Home with Beach & Dockage! Spectacular Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This elegant home is located on a beautiful 2.5 acre gated beachfront estate with amazing views of our beautiful island ...
From $880 per night (USD)Expedia
From $192 per night (USD)VRBO
Luxurious 2BR Beachfront Condo | Steps to Pool & Ocean | Ocean Point Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to Island Time 🏝️—your beachfront escape in beautiful Key Largo. Wake up to gentle ocean breezes, step ...
From $192 per night (USD)VRBO
From $331 per night (USD)Expedia
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful newly refreshed vacation rental is all about the view. It is upstairs with an unobstructed view of the Fl ...
From $331 per night (USD)Expedia
From $313 per night (USD)VRBO
Canal-front home remodeled for HGTV with private swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
La Pirata Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $313 per night (USD)VRBO
From $435 per night (USD)Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $435 per night (USD)Expedia
From $1872 per night (USD)VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $1872 per night (USD)VRBO
From $467 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $467 per night (USD)Expedia
From $475 per night (USD)VRBO
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $475 per night (USD)VRBO
From $741 per night (USD)Expedia
Waterfront Duck Key Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
From $741 per night (USD)Expedia
From $248 per night (USD)VRBO
Vacation like a local
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $248 per night (USD)VRBO
From $557 per night (USD)Expedia
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are proud to announce- Castaway Island has been named for 2024’s KW people’s choice awards as a FINALIST for Best Va ...
From $557 per night (USD)Expedia
From $250 per night (USD)VRBO
COCONUT Adorable cottage in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $250 per night (USD)VRBO
From $217 per night (USD)Expedia
Ocean Shores Home Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $217 per night (USD)Expedia
From $349 per night (USD)VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $349 per night (USD)VRBO
From $243 per night (USD)Expedia
Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
White Palm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $243 per night (USD)Expedia
From $387 per night (USD)VRBO
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When your vac ...
From $387 per night (USD)VRBO
From $324 per night (USD)Expedia
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SET SAIL cele ...
From $324 per night (USD)Expedia