
Stock Island Rentals

- From $1038 per night (USD)
VRBO
Amazing Land and Sea Getaway! Four Convenient Rooms, Close to Nearest Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1038 per night (USD)VRBO
- From $1038 per night (USD)
Expedia
Ideal Location for Family and Friends! Four Spacious Rooms, Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1038 per night (USD)Expedia
- From $619 per night (USD)
VRBO
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Book now!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe! **Reservations are available in weekly (7 ...
From $619 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Perfect Staycation! Close to Local Attractions! Deluxe Room w\/ Pool View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $242 per night (USD)Expedia
- From $931 per night (USD)
VRBO
Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the G ...
From $931 per night (USD)VRBO
- From $831 per night (USD)
Expedia
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $831 per night (USD)Expedia
- From $1181 per night (USD)
VRBO
Enjoy a Hassle-Free and Soothing Stay! 4 Amazing Units w\/ Terrace! Pool, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1181 per night (USD)VRBO
- From $295 per night (USD)
Expedia
King with Pool View & Terrace at The Gates Hotel Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $295 per night (USD)Expedia
- From $885 per night (USD)
VRBO
3 x King with Pool View & Terrace at The Gates Hotel Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $885 per night (USD)VRBO
- From $591 per night (USD)
Expedia
2 x King with Pool View & Terrace at The Gates Hotel Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $591 per night (USD)Expedia
- Click For Pricing
VRBO
Key West - President’s Week!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful condo located at Hyatt Windward Pointe in Key West. Close to airport, Smather’s Beach, East Martello Museum; 3 ...
Click For PricingVRBO
- Click For Pricing
Expedia
AVAILABLE Jan 28 - Feb 11, 2023! Hyatt Windward Point Resort, Key West FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Windward Pointe is an exclusive 93 unit residential-style resort with ocean views, free-form pool and lush landsca ...
Click For PricingExpedia
- From $556 per night (USD)
VRBO
Balcony, Pool, & Pet Friendly - The Grenada Suite
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $556 per night (USD)VRBO
- From $2062 per night (USD)
Expedia
Yacht Hatteras 60'
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Listing description You won’t forget your time aboard this romantic 60' Hatteras yacht, including 30" Catamaran tender w ...
From $2062 per night (USD)Expedia
- From $1245 per night (USD)
VRBO
4 x The Scene 2 Queens at The Gates Hotel Key West, Pool View
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1245 per night (USD)VRBO
- From $934 per night (USD)
Expedia
Enjoy a Hassle-Free Stay! 3 Awesome Units, Pet-friendly! Pool & Shuttle Service
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $934 per night (USD)Expedia
- From $622 per night (USD)
VRBO
Paradise Found! 2 Comfortable & Modern Units! Onsite Pool, Private Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $622 per night (USD)VRBO
- From $1245 per night (USD)
Expedia
Best Place to Stay in Key West! 4 Stylish Units, Pool! Parking & EV Charger
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1245 per night (USD)Expedia
- From $934 per night (USD)
VRBO
3x Double Queens With Terrace at The Gates Hotel Key West, Pets Allowed
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $934 per night (USD)VRBO
- Click For Pricing
Expedia
Hyatt Beach House - 2 bedroom condo - sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Popular springbreak week and availability goes fast! Grab it now before it's gone! Availability: 3/24/2024 (Sun) - 3/31 ...
Click For PricingExpedia
- From $449 per night (USD)
VRBO
Dog-friendly suite with pool, hot tub, tennis & full kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Suites - Dominican Suite 110 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $449 per night (USD)VRBO
- From $462 per night (USD)
Expedia
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Martinique Suite 108 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $462 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Remodeled cozy retreat - Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick off your flip flops in this wonderful newly renovated 1 bed,1 bath guest house! After a day at the beach or a late ...
From $144 per night (USD)VRBO
- Click For Pricing
Expedia
KEY WEST PARADISE- YOUR HAPPY PLACE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and Marina is located on Roosevelt Blvd, just off of Route 1. Features two pools, a jacuzzi and a ...
Click For PricingExpedia
- From $957 per night (USD)
VRBO
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $957 per night (USD)VRBO
- From $904 per night (USD)
Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)VRBO
- From $904 per night (USD)
Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)Expedia
- From $904 per night (USD)
VRBO
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)VRBO
- From $1014 per night (USD)
Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $1014 per night (USD)Expedia
- From $904 per night (USD)
VRBO
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)VRBO
- From $932 per night (USD)
Expedia
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $932 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)VRBO
- From $932 per night (USD)
Expedia
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $932 per night (USD)Expedia
- From $904 per night (USD)
VRBO
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)VRBO
- From $904 per night (USD)
Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)VRBO
- From $943 per night (USD)
Expedia
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)VRBO
- From $904 per night (USD)
Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)VRBO
- From $904 per night (USD)
Expedia
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)Expedia
- From $904 per night (USD)
VRBO
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)VRBO
- From $1058 per night (USD)
Expedia
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $1058 per night (USD)Expedia
- From $591 per night (USD)
VRBO
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $591 per night (USD)VRBO
- From $588 per night (USD)
Expedia
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $588 per night (USD)Expedia
- From $591 per night (USD)
VRBO
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $591 per night (USD)VRBO
- From $730 per night (USD)
Expedia
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $730 per night (USD)Expedia
- From $630 per night (USD)
VRBO
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $630 per night (USD)VRBO
- From $584 per night (USD)
Expedia
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $584 per night (USD)Expedia
- From $591 per night (USD)
VRBO
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $591 per night (USD)VRBO
- From $584 per night (USD)
Expedia
Two Bedroom Residence
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $584 per night (USD)Expedia
- From $904 per night (USD)
VRBO
Pool View 3BR Residence | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $904 per night (USD)VRBO
- From $943 per night (USD)
Expedia
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)Expedia
- From $943 per night (USD)
VRBO
Ocean Front Presidential Suite | Beachside Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...
From $943 per night (USD)VRBO
- From $311 per night (USD)
Expedia
Hyatt Vacation Club Windward Pointe Key West. Spectacular Key West Ocean Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Vacation Club Windward Pointe Key West 2br/2ba/6ppl Fantastic location!!! Saturday to Saturday 7 night rental at H ...
From $311 per night (USD)Expedia
- Click For Pricing
VRBO
Fantasy Fest Week!! Spacious 2-Bedroom Suite Hyatt Windward Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This unit is available 10/22/23-10/28/23 for 6 nights! Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blend ...
Click For PricingVRBO
- From $944 per night (USD)
Expedia
3-bedroom condo in Key West with 180 degree Ocean View\/Marina View Cold AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Key West is waiting for you at this 3-bedroom Condo. Spectacular 180 degree view of the Ocean and Yachts in the Marina. ...
From $944 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come and experience living the FLORIDA KEYS dream. As seen on the TV show “ My Floating Home”. This charming tiny float ...
From $278 per night (USD)VRBO
- Click For Pricing
Expedia
Charming 2-bedroom resort with WiFi, AC in gorgeous Key West. Quiet & relaxing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your home away from home in Key West with 2 bedrooms. This enchanting resort offers a cozy living room with a sofa bed, ...
Click For PricingExpedia
- Click For Pricing
VRBO
Hyatt Windward Pointe 2BR in Key West 6\/22\/2024 to 6\/29\/2024 for 7 nights
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for 7 nights from Saturday 6/22/2024 to Saturday 6/29/2024 only (Dates cannot be changed.). Hyatt Wind ...
Click For PricingVRBO
- From $659 per night (USD)
Expedia
Stay at SUNRISE SUITES 203!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suite 203 is a quiet alternative to the bustling noise of downtown Key West. Located just a 10-minute drive from ...
From $659 per night (USD)Expedia
- From $632 per night (USD)
VRBO
Retreat to RUM CAY @ Sunrise Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rum Cay offers a quiet alternative to the downtown area of Key West. This modern condo is located a short 10-minute ride ...
From $632 per night (USD)VRBO
- Click For Pricing
Expedia
You Found the One!!! Approx 4 miles from Duval St. 2 BDRM 2BATH CONDO. SLEEPS 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sleeps up to 6 guests Lush tropical beauty welcomes you to a spacious residential-style condominium featuring a primary ...
Click For PricingExpedia
- From $656 per night (USD)
VRBO
Butterfly Nest | Newly Updated w\/ Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Butterfly Nest | Newly Updated w/ Shared Pool Escape to Butterfly Nest, a serene, beautifully designed 2-bedroom condo ...
From $656 per night (USD)VRBO
- From $539 per night (USD)
Expedia
The Andros | Incredible Views w\/ Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Andros | Incredible Views w/ Shared Pool Escape to The Andros, a serene, beautifully designed 2-bedroom, 2-bath con ...
From $539 per night (USD)Expedia
- From $894 per night (USD)
VRBO
Oceanfront Resort, Thanksgiving Week, Infinity Pool, Hot Tub, Sleeps 6, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your Thanksgiving vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished ...
From $894 per night (USD)VRBO
- Click For Pricing
Expedia
Oceanfront Resort, Infinity Pool, Hot Tub, Courtyard, Sleeps 6, 7 Nights, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished condo style r ...
Click For PricingExpedia
- From $403 per night (USD)
VRBO
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
**Escape to Paradise on a Floating Retreat in Key West!** Welcome to your unforgettable getaway aboard this gemini sa ...
From $403 per night (USD)VRBO
- From $894 per night (USD)
Expedia
Oceanfront Resort, Fantasy Fest, Infinity Pool, Hot Tub, Sleeps 6 7 Nites, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have I mentioned that this listing is for celebrating Fantasy Fest in sunny Key West, FL? You will be staying at the Hya ...
From $894 per night (USD)Expedia
- From $530 per night (USD)
VRBO
Sea Breeze Suite 101 - Reduced Nightly Rates for April!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
SPECIAL PRICING!! April! Saltwater Stays is the new property manager, bringing top-notch local service to your stay. B ...
From $530 per night (USD)VRBO
- From $838 per night (USD)
Expedia
Waterfront Resort, RWO Championship Boat Races, Pool, Hot Tub, Sleeps 6, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have I mentioned that this listing is for Race World Offshore Power Boat World Championship Races in sunny Key West, FL? ...
From $838 per night (USD)Expedia
- From $979 per night (USD)
VRBO
Waterfront Resort, Fantasy Fest, Private Beach, Boat Docks, Sleeps 6, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have I mentioned that this listing is for celebrating Fantasy Fest in sunny Key West, FL? You will be staying at the Hya ...
From $979 per night (USD)VRBO
- From $669 per night (USD)
Expedia
Waterfront Resort, Private Beach, Boat Docks, Sleeps 6, Pool, Hot Tub, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Beach House in sunny Key West, FL; 7 nights; fully furnished condo style resid ...
From $669 per night (USD)Expedia
- From $669 per night (USD)
VRBO
Oceanfront Resort, Infinity Pool, Hot Tub, Courtyard, Sleeps 6, 7 Nights, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished condo style r ...
From $669 per night (USD)VRBO
- Click For Pricing
Expedia
Oceanfront Resort, Infinity Pool, Hot Tub, Courtyard, Sleeps 6, 7 Nights, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your vacation get-away at the Hyatt Windward Pointe in sunny Key West, FL; 7 nights; fully furnished condo style r ...
Click For PricingExpedia
- From $356 per night (USD)
VRBO
NEW monthly LISTING: 3000+ SQUARE FOOT HOME 0N OVER 1\/4 ACRE POOL SPA AND GARDEN
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 7
BEDAZZLING COMPOUND... This wonderful home is situated on a tremendously landscaped and walled double lot in New Town. ...
From $356 per night (USD)VRBO
- From $720 per night (USD)
Expedia
The Salt Cay | Updated! Stunning Sunset View, Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Salt Cay | Updated! Stunning Sunset View, Pool! Escape to The Salt Cay, a serene, beautifully updated, and well-app ...
From $720 per night (USD)Expedia
- From $427 per night (USD)
VRBO
Double Cabin Luxury Power Motor Yacht in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a five star marina in key west on a double cabin luxury power motor yacht. This amazing property features 1 king b ...
From $427 per night (USD)VRBO
- From $386 per night (USD)
Expedia
Charming Key West Town Home Beach\/Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Home of Famous Ernest Hemingway and Jimmy Buffet. Enjoy the downtown area on Duval Street where Sloppy Joe's and Captain ...
From $386 per night (USD)Expedia
- From $377 per night (USD)
VRBO
Key Haven Coastal Retreat - Canal front with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Key Haven Coastal Retreat – Your Private Waterfront Paradise Discover luxury island living at Key Haven Coas ...
From $377 per night (USD)VRBO
- From $1350 per night (USD)
Expedia
Charming 2-bedroom resort with WiFi, fitness room in phenomenal Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this enchanting 2-bedroom gem in Key West. This charming resort boasts a cozy atmosphere with 1 king bed and 2 ...
From $1350 per night (USD)Expedia
- Click For Pricing
VRBO
Key West, Hyatt Condo, 4 nights ONLY, Sun, 3\/16 out Thurs, 3\/20\/25
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Condo, Hyatt Beach House, 4 nights ONLY, in Sun, March 16, out Thurs, March 20, 2025, Hyatt Beach House, 2 Bedr ...
Click For PricingVRBO
- From $544 per night (USD)
Expedia
The Samana Cay | Tropical, Airy Retreat w\/ Private Balcony & Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Samana Cay | Tropial, Airy Retreat w/ Private Balcony & Pool! Escape to The Samana Cay, a bright and inviting 2-bed ...
From $544 per night (USD)Expedia
- From $342 per night (USD)
VRBO
Poolside Suite with Direct Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $342 per night (USD)VRBO
- From $342 per night (USD)
Expedia
Poolside Suite with Direct Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $342 per night (USD)Expedia
- From $342 per night (USD)
VRBO
Poolside Suite with Direct Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $342 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Poolside Suite with Direct Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in ...
From $340 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Sunrise Condo at Seaside - KEY WEST!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
SUMMER SALE! Sunrise Condo at Seaside The owners of this unit have made some great improvements! New TVs, faster WiFi, ...
From $311 per night (USD)VRBO
- From $495 per night (USD)
Expedia
Hyatt Beach House 2 BR Condo in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spend your days relaxing by the zero-entry pool or at our white sandy beach, furnished with thick-cushioned chairs, picn ...
From $495 per night (USD)Expedia
- From $484 per night (USD)
VRBO
Hyatt Beach House in Key West- 2br- luxury vacation rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2br condo that sleeps six confirmed for check in March 9 to 16, 2025! Hyatt's Beach House Resort continues the traditi ...
From $484 per night (USD)VRBO
- From $774 per night (USD)
Expedia
3-bedroom ocean view condo in delightful Key West with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover this delightful 3-bedroom gem in Key West. This charming condo features 1 king bed, 1 queen bed, and 2 twin bed ...
From $774 per night (USD)Expedia
- From $530 per night (USD)
VRBO
Cozy houseboat Felix the Cat Experience with AC and WiFi @ The Perry
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome aboard our cozy houseboat nestled in the Perry Marina! Uniquely crafted by legendary artist, immerse yourself in ...
From $530 per night (USD)VRBO
- From $481 per night (USD)
Expedia
Cozy Sea Ray Yacht with Flybridge Views, 2 Staterooms @ The Perry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome aboard the Cozy Yacht Experience at the Perry marina! This yacht features two staterooms, a fully equipped galle ...
From $481 per night (USD)Expedia
- From $152 per night (USD)
VRBO
NEW LISTING - CHARMING 2-BEDROOM CONDO IN BEAUTIFUL KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We just purchased our 2-bedroom, 2-bathroom property at the beautifully landscaped Las Salinas Condominiums in Key West. ...
From $152 per night (USD)VRBO
- From $1450 per night (USD)
VRBO
2| Coconut Mallory | Lux Stay | Pool | Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Marina & Resort is a perfect blend of Key West’s laid-back charm and modern resort luxury. Nestled near ...
From $1450 per night (USD)VRBO
- From $1129 per night (USD)
VRBO
Hyatt Beach House Resort Key West 1-7 nights
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1 night stays, 2 Bedroom 2 Bath Full kitchen w/all essentials Washer/Dryer elevator & free parking. Some 2 night stays c ...
From $1129 per night (USD)VRBO
- From $616 per night (USD)
Expedia
Hyatt Windward Pointe 2 bdrm 2 ba full kitch view\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom suites sleep 6. Full kitchen, dining area, washer/dryer, balcony terrace. There are mostly 4 night stays, but ...
From $616 per night (USD)Expedia
- From $591 per night (USD)
VRBO
Paradise Found! 2 Comfortable and Modern Units, Swimming Pool, Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $591 per night (USD)VRBO
- From $622 per night (USD)
Expedia
2 Double Queens With Terrace at The Gates Hotel Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $622 per night (USD)Expedia