Stock Island Rentals
- From $1400 per night (USD)
VRBO
2\/2 BEDROOM SUITE - HYATT WINDWARD POINT - KEY WEST - BEACH FRONT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...
From $1400 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Casa Caribe Beautiful tropical 2 bedroom sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical 2 bedroom, 2.5 bathroom, 2 level Key West townhome to be your home away from home! No detail has been overlooke ...
From $399 per night (USD)Expedia
- From $480 per night (USD)
VRBO
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Poseidon's Paradise, your ultimate luxurious waterfront escape in Key West! Nestled on the picturesque Rivier ...
From $480 per night (USD)VRBO
- From $1110 per night (USD)
VRBO
2\/2 BEDROOM SUITE - COCONUT MALLORY MARINA & RESORT - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Let your spirit rejuvenate and your soul relax in lush tropical surroundings at the Coconut Mallory Marina & Resort! Loc ...
From $1110 per night (USD)VRBO
- From $738 per night (USD)
VRBO
VRBO Exclusive Offer! 51' Catamaran Yacht located in a Beautiful Resort!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
You and your guests will have exclusive use of this 51 ft yacht all to yourselves. The yacht stays docked, the entire re ...
From $738 per night (USD)VRBO
- From $331 per night (USD)
VRBO
Paradise Found! Outdoor Pool, Pets Allowed, Minutes From Smathers Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $331 per night (USD)VRBO
- From $385 per night (USD)
VRBO
A Conch Casita at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unique home in Key West Golf Club Club Community coming soon for rental. ***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY** ...
From $385 per night (USD)VRBO
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Expedia
Your Key West Private Poolside Paradise
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This gorgeous Key Haven waterfront home has maximized outdoor living space to make the most of Keys living. Picturesque ...
Click For PricingExpedia
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VRBO
Hyatt Residence Club Key West, Beach House: 2 Bed\/2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a luxurious experience when you stay at this special place. Welcome to your own private sanctuary among the lush l ...
Click For PricingVRBO
- From $525 per night (USD)
VRBO
Willie Nelson Week- 2 BR rental Feb 11-18, 2024 Hyatt Beach House on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Top notch quality Hyatt resort on the water with wade-in pool and screened-in porch. This is a 7 day minimum-7 day maxim ...
From $525 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Beautiful Key West Townhome
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come on in, relax and enjoy our wonderful slice of paradise. Over 2,000 square feet of luxurious living space. Our two b ...
From $350 per night (USD)VRBO
- From $499 per night (USD)
VRBO
7 day rental March 31, 2024 Hyatt Condo. Waterfront-Two BR. Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Top notch quality Hyatt resort on the water with wade-in pool and screened-in porch. This is a 7 day minimum-7 day maxim ...
From $499 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Hyatt Windward Point Resort - Top Floor Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
One of 93 exclusive units in a resort-style complex with lush landscape, large free flowing pool, sauna, beach volleybal ...
From $475 per night (USD)VRBO
- From $475 per night (USD)
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 ...
From $475 per night (USD)Expedia
- From $189 per night (USD)
VRBO
The Grenada Suite | Pool View & Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $189 per night (USD)VRBO
- From $1833 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 $1833 per night (USD)Expedia
- From $242 per night (USD)
VRBO
Lovely 1 bedroom in Stock Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our lovely one bedroom apartment located in Stock Island is the perfect place for your Key West getaway. Located only tw ...
From $242 per night (USD)VRBO
- From $227 per night (USD)
VRBO
The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $227 per night (USD)VRBO
- Click For Pricing
VRBO
4 x Standard King Accessible with Roll In Shower at The Gates Hotel Key West
- Bedrooms:
- 4
- Bathrooms:
- 0
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
Click For PricingVRBO
- From $528 per night (USD)
VRBO
2 x The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $528 per night (USD)VRBO
- Click For Pricing
VRBO
Ultimate Key West Escape! 3 Classy Units for Large Groups! Swimming Pool
- 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 ...
Click For PricingVRBO
- From $555 per night (USD)
VRBO
Escape to the Keys! 2 Family-friendly Units w\/ Parking! Outdoor Swimming Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $555 per night (USD)VRBO
- Click For Pricing
VRBO
3 x The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
- 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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Escape to the Keys! 4 Modern Pet-friendly Units! Parking and EV Charger! Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
Click For PricingVRBO
- From $712 per night (USD)
VRBO
Make Your Trip More Enjoyable! 3 Stylish Units! Pool, Parking & EV Charger
- Bedrooms:
- 3
- Bathrooms:
- 0
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $712 per night (USD)VRBO
- From $1197 per night (USD)
VRBO
4 x The Scene 2 Queens at The Gates Hotel Key West
- 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 $1197 per night (USD)VRBO
- From $972 per night (USD)
VRBO
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 $972 per night (USD)VRBO
- From $555 per night (USD)
VRBO
Everything You Need For The Perfect Vacation! 2 Modish Units, On-site Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $555 per night (USD)VRBO
- From $616 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 $616 per night (USD)VRBO
- Click For Pricing
VRBO
Get Ready for Blissful Getaway! 4 Homely Units! Bike Rentals, Pool and Parking!
- Bedrooms:
- 4
- Bathrooms:
- 0
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
Click For PricingVRBO
- Click For Pricing
VRBO
4 x King with Pool View & Terrace at The Gates Hotel Key West
- 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 ...
Click For PricingVRBO
- From $648 per night (USD)
VRBO
2 x The Scene 2 Queens 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 $648 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Make Your Trip More Enjoyable! 3 Perfect Units for Large Group! On-site Pool
- 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 ...
Click For PricingVRBO
- From $1131 per night (USD)
VRBO
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 $1131 per night (USD)VRBO
- From $367 per night (USD)
VRBO
Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! Pool
- 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 $367 per night (USD)VRBO
- From $749 per night (USD)
VRBO
3 x Standard King Accessible with Roll In Shower at The Gates Hotel Key West
- Bedrooms:
- 3
- Bathrooms:
- 0
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $749 per night (USD)VRBO
- From $926 per night (USD)
VRBO
3 x The Scene 2 Queens at The Gates Hotel Key West
- 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 $926 per night (USD)VRBO
- From $211 per night (USD)
VRBO
Standard King Accessible w\/ Roll In Shower at The Gates Hotel Key West
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $211 per night (USD)VRBO
- From $528 per night (USD)
VRBO
2 x Standard King Accessible with Roll In Shower 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 $528 per night (USD)VRBO
- From $562 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 $562 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Get Ready for Blissful Getaway! Modish Unit, Swimming Pool! Parking & EV Charger
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $261 per night (USD)VRBO
- From $301 per night (USD)
VRBO
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 $301 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $533 per night (USD)
VRBO
2 x King with Pool View & Terrace at The Gates Hotel Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $533 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Explore Fort East Martello Museum! Modern Unit w\/ Outdoor Pool! Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $239 per night (USD)VRBO
- Click For Pricing
VRBO
4 x The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $571 per night (USD)
VRBO
Beautiful Key West Resort! Hyatt Windward Pointe two bedroom. Book now!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are able to offer 7 night weekly rentals with check-in on Fridays, Saturdays, and Sundays only. Hyatt Windward Poin ...
From $571 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Cozy Camper in Stock Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our lovely cozy camper is located in Stock Island is the perfect place for your Key West getaway. Located only two block ...
From $202 per night (USD)Expedia
- From $459 per night (USD)
VRBO
40'yacht in Paradise Awaits You!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
**** This boat is currently located at Stock Island Yacht Club and Marina at 6000 Peninsular Ave, Key West FL****. We d ...
From $459 per night (USD)VRBO
- From $1950 per night (USD)
Expedia
Celebrate New Years Eve in Key West @ Exclusive Hyatt Windward - SLEEPS 6 !
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IMPORTANT...THIS RENTAL IS AVAILABLE FOR ONE NIGHT CHECKING IN DECEMBER 31, 2024 AND CHECKING OUT JANUARY 1ST, 2025. PLE ...
From $1950 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $316 per night (USD)
Expedia
Dog-friendly suite with pool, hot tub, tennis & full kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Dominican Suite 110 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $316 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Hyatt Beach House Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Hyatt Residence Club Beach House on Key West has a private beach, boat dock, and tiki bar. Room includes washer and ...
From $350 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Peaceful 1 bedroom at Leo's
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our lovely one bedroom apartment located in Stock Island is the perfect place for your Key West getaway. Located only tw ...
From $239 per night (USD)Expedia
- From $242 per night (USD)
VRBO
Fun & Energetic 2 Bed 1.5 Bath: Booty Caye @ Key West Golf Club - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to your private oasis at Booty Caye, nestled within the exclusive enclave of the Key West Golf Club. This beautif ...
From $242 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Stylish 2\/2 pool\/gym\/tennis\/hot tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Comfortable and serene, this fully updated condo offers numerous upscale resort amenities. Explore Old Town Key West, a ...
From $450 per night (USD)Expedia
- Click For Pricing
VRBO
Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
Click For PricingVRBO
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Expedia
FANTASY FEST WEEK 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
When not enjoying Fantasy Fest relax by the pool or lunch etc at Abbey Road bar and restaurant on premises. Rooms are s ...
Click For PricingExpedia
- From $423 per night (USD)
VRBO
3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel\/Marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Living room, Dining room and kitchen all enjoy stunning views of the Atlantic Ocean. Master bedroom and Master bath also ...
From $423 per night (USD)VRBO
- Click For Pricing
Expedia
Breezy Condo w\/ Private Deck, Shared Pool\/Hot Tub, & Parking Space - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Cayo Cruz Suite 308 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
Click For PricingExpedia
- From $303 per night (USD)
VRBO
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 $303 per night (USD)VRBO
- From $125 per night (USD)
Expedia
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 $125 per night (USD)Expedia
- From $636 per night (USD)
VRBO
Excellent Choice! Three Family-friendly Rooms, Fantastic View, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $636 per night (USD)VRBO
- From $212 per night (USD)
VRBO
Best Spot For Your Next Trip! Deluxe Room w\/ 2 Queen Beds, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $212 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Amazing Room with Stunning Ocean View Close to Beach! w\/ Outdoor Swimming Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $315 per night (USD)VRBO
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Expedia
Waterfront condo, 2 bed, full kitchen, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a Florida destination renowned for its hospitality and relaxed atmosphere. Set on the northeastern corner of t ...
Click For PricingExpedia
- From $509 per night (USD)
VRBO
Oceanfront 3 bedroom gated Condominium adjacent Marina, and Restaurant.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Living room, Dining room and kitchen all enjoy stunning views of the Atlantic Ocean. Master bedroom and Master bath also ...
From $509 per night (USD)VRBO
- Click For Pricing
Expedia
Renovated condo with on-site pool, spa, rec courts, & private balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Salty Sunrise #311 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $450 per night (USD)
VRBO
Penthouse in Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory is a waterfront private community that provides resort-style amenities, including two large pools, Jacuz ...
From $450 per night (USD)VRBO
- Click For Pricing
Expedia
Oceanfront Resort 2 bedrooms sleeps 6.Check in December 22-29.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Luxury 5 star vacation resort on the water. 2 bedroom spacious condo with sleeper sofa. Unit sleeps 6. You deserve this! ...
Click For PricingExpedia
- From $195 per night (USD)
VRBO
Island Retreat - Key West Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful 2 bed, 2 bath condo is newly listed after a complete renovation, including all new furniture and improvem ...
From $195 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Beautiful 43 ' sportfish yacht
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Friendly Key West style marina. Boat is secure, won't notice any movement! Just steps from the famous Hogfish Tiki Bar ...
From $315 per night (USD)VRBO
- From $750 per night (USD)
VRBO
HYATT RESIDENCE CLUB WINDWARD POINTE RESORT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come to the Hyatt Residence Club, Windward Pointe. Immerse yourself in a location away from the hustle and bustle of Du ...
From $750 per night (USD)VRBO
- From $182 per night (USD)
Expedia
Sunset Marina | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Unit C203 at 5601 College Road, a stylish and Vibrant residence located in the Sunset Marina Complex. This mo ...
From $182 per night (USD)Expedia
- From $314 per night (USD)
VRBO
The Flight Deck - 3 Bedroom \/ 3 Bathroom with Shared Pool & Fitness Center!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to “The Flight Deck” located in sunny Key West, Florida on Stock Island. This spacious and accommodating 3 bed ...
From $314 per night (USD)VRBO
- From $270 per night (USD)
Expedia
2 Bedroom Townhome on Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $270 per night (USD)Expedia
- From $475 per night (USD)
VRBO
Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Keep it simple! This peaceful & centrally-located 3 bedroom 2 bathroom pool home at Mile Marker 5 in Key Haven. One lev ...
From $475 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Tropical Paradise set along the Atlantic Ocean minutes to Old Town Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous views of the tropical grounds and the Atlantic Ocean from your balcony. A full kitchen and modern decor through ...
From $550 per night (USD)VRBO
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VRBO
Waterfront Resort, New Year’s Eve, Hyatt, 2 Nights, Sleeps 6, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key W ...
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Expedia
WATER FRONT LOCATION WITH GREAT LOCATION TO KEY WEST.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A BOATER'S DREAM LOCATION! KAYAKER AND PADDLEBOARDER HEAVEN WITH RESORT QUAILTYAMENITIES! Dock your boat in your backya ...
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VRBO
Hyatt Beach House Resort, Key West, Florida - FANTASY FEST WEEK 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
October 22-29 2023 Includes $35.00 Hyatt guest pass fee. All other resort fee's are the responsibility of the renter. ...
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- From $250 per night (USD)
Expedia
A Poolside Cabana at the Key West Golf Club!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
A Poolside Cabana--Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort ...
From $250 per night (USD)Expedia
- From $449 per night (USD)
VRBO
Coconut Mallory Resort Two Bedroom Condo with Full Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Time to chill at the perfect a beer or glass of wine at the bar directly on the water with canal views. Just a mile fro ...
From $449 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Boater’s Paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bright, open, and airy Old Florida single story home. Safe, family neighborhood. Deep water canal with quick access to ...
From $500 per night (USD)VRBO
- From $180 per night (USD)
VRBO
17 Kingfisher Lane | 2 Bed, 2 Bath
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Experience luxury and comfort in our stunning vacation rental property in the heart of Key West Golf Club. This 2-story ...
From $180 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Gone Coastal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful places to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral ...
From $399 per night (USD)Expedia
- From $425 per night (USD)
VRBO
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 ...
From $425 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Casa de Playa -New Unit available for winter season at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Casa de Playa - This is a beautiful, private, two-story open plan townhome in the Sanctuary at Key West Golf Club with p ...
From $275 per night (USD)Expedia
- From $177 per night (USD)
VRBO
Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tarpon Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $177 per night (USD)VRBO
- From $800 per night (USD)
Expedia
New! Crestwood House by Brightwild | Huge Pool
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: Welcome to Key Haven Estates! The Crestwood is one of four newly designed homes on the exclusive island of Key ...
From $800 per night (USD)Expedia
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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 ...
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- From $101 per night (USD)
Expedia
Colorful home in private community with resort pool & hot tub, on-site golf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Egret House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $101 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Available Oct19-Oct 26 and Oct26-Nov 2 Only these dates are available
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WINDWARD POINTE HYATT PROPERTY LOCATED AT 3675 S ROOSEVELT BLVD KEY WEST FL. These last two weeks of October available. ...
From $257 per night (USD)VRBO
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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!!! Sunday to Sunday 7 night rental at HYATT ...
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VRBO
Waterfront Retreat, Offshore Boat Races, 7 Nights, Sleeps 6, Beach, Docks, Hyatt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary amongst the lush landscape of Key W ...
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- From $800 per night (USD)
Expedia
New! Altair House by Brightwild | Pool, Pets!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: Welcome to Key Haven Estates! The Altair is one of four brand-new homes located on the exclusive island of Key ...
From $800 per night (USD)Expedia
- From $242 per night (USD)
VRBO
New Listing-Golf Course Charmer!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
From $242 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Private & Haven-ly pool home on boating canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
About this space This Haven-ly Marina home is a picture perfect Keys escape. The 2 bed/2 bath main home and 1/1 casita i ...
From $300 per night (USD)Expedia