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Stock Island Rentals

From $578 per night (USD)
VRBO
2 BR 7 day rental One Week only in March 23- 30 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 $578 per night (USD)
VRBO
From $539 per night (USD)
Expedia
7 day rental Feb 2 -9, 2025 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 $539 per night (USD)
Expedia
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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 ...
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VRBO
From $619 per night (USD)
Expedia
Beautiful 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)
Expedia
From $885 per night (USD)
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 ...
From $885 per night (USD)
VRBO
From $312 per night (USD)
Expedia
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 $312 per night (USD)
Expedia
From $686 per night (USD)
VRBO
Hyatt Beach House- 2 Bedroom Located On The Gulf With Private White Sand Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Beach House! **Reservations are available in weekly (7 nigh ...
From $686 per night (USD)
VRBO
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Expedia
2br-2ba Hyatt Key West Florida • Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Celebrate New Years at this beautiful waterfront Hyatt resort in Key West. Enjoy 7 Nights at this beautiful Hyatt Resort ...
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Expedia
From $697 per night (USD)
VRBO
Excellent Choice! Three Family-friendly Rooms, Fantastic View, Outdoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $697 per night (USD)
VRBO
$Best Spot For Your Next Trip! Deluxe Room w\/ 2 Queen Beds, Onsite Pool$
From $242 per night (USD)
Expedia
Best Spot For Your Next Trip! Deluxe Room w\/ 2 Queen Beds, Onsite Pool
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
$Amazing Room with Stunning Ocean View Close to Beach! w\/ Outdoor Swimming Pool$
From $260 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 $260 per night (USD)
VRBO
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Expedia
Waterfront condo, 2 bed, full kitchen, pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a Florida destination renowned for its hospitality and relaxed atmosphere. Set on the northeastern corner of t ...
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Expedia
From $556 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 $556 per night (USD)
VRBO
From $225 per night (USD)
Expedia
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 $225 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tarpon Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $223 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $492 per night (USD)
VRBO
Beautiful Stock Island Rental ~10 Min from Downtown Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the tropics without leaving the states! Relax, and catch your breath while enjoying ocean views from the large pri ...
From $492 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coas ...
From $466 per night (USD)
Expedia
From $699 per night (USD)
VRBO
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coas ...
From $699 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Last Stop in Paradise
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This historic Key West home is a local favorite and loved for its charm - you will find the inside and outside is just s ...
From $361 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Poolside Cottage #412
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This s ...
From $360 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Poolside Cottage #411
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This s ...
From $360 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This condo is located approximately three miles from Duval and one mile from Smathers beach. Walking distance to the Oce ...
From $473 per night (USD)
VRBO
From $385 per night (USD)
Expedia
WINTER WEEK - KEY WEST - 2 Bedroom 2 Bathrooms Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Coconut Mallory Marina Resort - KEY WEST 2 Bedrooms 2 Bathroom Sleeps 6 Total. The Coconut Mallory Marina and Reso ...
From $385 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Cozy Salt Pond Condo Hideaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Freshly updated Salt Ponds condo located on Key West minutes from the beach , airport and downtown. Enjoy a soak in the ...
From $268 per night (USD)
VRBO
$Less Than 5 Miles to Beach! Gorgeous Room w\/ King Bed, Fantastic Views, Pool$
From $237 per night (USD)
Expedia
Less Than 5 Miles to Beach! Gorgeous Room w\/ King Bed, Fantastic Views, Pool
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 $237 per night (USD)
Expedia
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VRBO
Trawler 34 Californian Houseboat Fisherman's Cottage and Man Cave
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
36' Californian Cruiser/ MANCAVE NO FRILLS 1979 Portland Oregon 36 Californian Cruiser 1979 34'6" CALIFORNIAN MARSHALL ...
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VRBO
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Expedia
Cozy 1 bedroom apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cozy, clean and private 1 bed 1 bath apartment. Private entrance with free on street parking. Sleeps 4. Sorry, no pets! ...
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Expedia
From $233 per night (USD)
VRBO
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
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 $233 per night (USD)
VRBO
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Expedia
Rare on the island of Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
t's rare on the island of Key West but if you are looking for a beautiful completely renovated home, with privacy, water ...
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Expedia
$Sunrise 308-2BR\/2BA condo near beaches with pool, parking, balcony$
From $428 per night (USD)
VRBO
Sunrise 308-2BR\/2BA condo near beaches with pool, parking, balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $428 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Spacious Key West Condo at Coconut Mallory Resort & Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come and explore all that Key West has to offer! This unit at Coconut Mallory is a one level condo with both bedrooms a ...
From $394 per night (USD)
Expedia
$2\/2 Timeshare Rental - Only Available 12\/19 to 12\/22 and 12\/29 to 12\/30\/2024$
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VRBO
2\/2 Timeshare Rental - Only Available 12\/19 to 12\/22 and 12\/29 to 12\/30\/2024
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled on the quieter side of Key West, this water front condo is the perfect spot for your next getaway. This Key Wes ...
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VRBO
From $956 per night (USD)
Expedia
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beach House Resort + Amenities, 2-Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional ...
From $956 per night (USD)
Expedia
From $489 per night (USD)
VRBO
Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Poseidon Too! A completely, newly renovated two bedroom two bath condo located at Sunrise Suites. Poseidon To ...
From $489 per night (USD)
VRBO
From $367 per night (USD)
Expedia
**THE LARK’S LANDING @ SUNRISE SUITES** 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! Looking to la ...
From $367 per night (USD)
Expedia
Click For Pricing
VRBO
LAST MINUTE: 2BR Condo Key West for championship boat races!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BOAT WEEK - world championship race week!! Situated at the northeast corner of Key West, the lushly landscaped Beach ...
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VRBO
$Beautiful 2 Bedroom, 2 Bath Condo Resort on the Ocean in Key West. \n$
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Expedia
Beautiful 2 Bedroom, 2 Bath Condo Resort on the Ocean in Key West. \n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Partial ocean views and lavish decor welcome you to a two-bedroom villa offering a primary suite with a king bed and adj ...
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Expedia
$Studio with kitchenette, free parking, marina available 3\/12\/22 to 3\/19\/22 only<br>$
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VRBO
Studio with kitchenette, free parking, marina available 3\/12\/22 to 3\/19\/22 only<br>
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Renting timeshare: one week 3/12 check-in and 3/19 check-out for 2022. The studio condo (max 2 occupancy) at Coconut M ...
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VRBO
From $416 per night (USD)
VRBO
Hyatt Beach House - 2 Bedroom Waterfront Condo, 3 Night Stay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A tropical getaway in classic Key West style Escape to a Florida destination renowned for its hospitality and relax ...
From $416 per night (USD)
VRBO
From $107 per night (USD)
VRBO
Uptown quiet cottage close to beaches, restaurant & shopping.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Quiet cottage in a located in new town. Quick taxi ride or bus ride to downtown. Do your Duval Crawl & then head back to ...
From $107 per night (USD)
VRBO
$Sunrise 307-2BR\/2BA condo near beaches with pool, parking, balcony$
From $434 per night (USD)
Expedia
Sunrise 307-2BR\/2BA condo near beaches with pool, parking, balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $434 per night (USD)
Expedia
From $1123 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 $1123 per night (USD)
VRBO
$Castaway Cove: 2\/2 Condo near the beach with shared pool and hot tub$
From $484 per night (USD)
Expedia
Castaway Cove: 2\/2 Condo near the beach with shared pool and hot tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spen ...
From $484 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $355 per night (USD)
VRBO
From $551 per night (USD)
Expedia
Newly Renovated condo with scenic views, pool & hot tub, balcony, & parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Sunrise Suites - Saint Kitts 412 Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $551 per night (USD)
Expedia
From $3987 per night (USD)
VRBO
Luxury Motor Yacht Ready II Play
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Elevate your vacation experience by staying dockside aboard Motor Yacht Ready II Play, located on beautiful Okaloosa Isl ...
From $3987 per night (USD)
VRBO
$New Listing! Key Lime Paradise\/Condo$
From $645 per night (USD)
Expedia
New Listing! Key Lime Paradise\/Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come find your slice of paradise in this 2 bed 2 full bath newly renovated condo. This listing is perfect for those want ...
From $645 per night (USD)
Expedia
From $838 per night (USD)
VRBO
Oceanfront 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)
VRBO
$Cat Island Suite | Beautifully Renovated w\/ Pool!$
From $537 per night (USD)
Expedia
Cat Island Suite | Beautifully Renovated w\/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cat Island Suite | Updated! Stunning Sunset View, Pool! Escape to Cat Island Suite, a serene, beautifully updated, and ...
From $537 per night (USD)
Expedia
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VRBO
2-bedroom condo in lovely Key West with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful condo offers a superb retreat for guests. With 2 bedrooms featuring a king and quee ...
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VRBO
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Expedia
Hyatt Vacation Club at Beach House, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Lush tropical beauty welcomes you to a spacious residential-style villa featuring a primary bedroom with a king-size bed ...
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Expedia
$Hyatt Beach House, Key West, 4 Nights ONLY, in Sun, 07\/13, out Thurs, 07\/17\/2025$
From $506 per night (USD)
VRBO
Hyatt Beach House, Key West, 4 Nights ONLY, in Sun, 07\/13, out Thurs, 07\/17\/2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Hyatt Beach House, Key West adventure begins at this spacious 2-bedroom residential style hotel villa with a fully ...
From $506 per night (USD)
VRBO
From $422 per night (USD)
Expedia
NEW VRBO Listing! Elegant 40' Yacht in 5-Star Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire res ...
From $422 per night (USD)
Expedia
From $634 per night (USD)
VRBO
Oceans Edge Key West Resort, Hotel & Marina!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This stylish place to stay is perfect for group trips. This smoke-free hotel features a marina, 6 outdoor pools, and a r ...
From $634 per night (USD)
VRBO
From $1426 per night (USD)
Expedia
Windward Point Beachfront Resort, Hot Tub, Pool
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 $1426 per night (USD)
Expedia
From $1426 per night (USD)
VRBO
Windward Point Beachfront Resort, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the glamour of this stylish, upscale place. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the ...
From $1426 per night (USD)
VRBO
From $1545 per night (USD)
Expedia
Mallory Resort, Beach, Hot Tub, Pool, BBQ, Marina
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 $1545 per night (USD)
Expedia
From $1450 per night (USD)
VRBO
Oceans Edge Key West Resort, Hotel & Marina!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in an upscale place that's near everything you want to visit. Located in Key West, Oceans Edge Key West Resort, Hot ...
From $1450 per night (USD)
VRBO
From $1308 per night (USD)
Expedia
Hyatt Beach House Residences! Keys, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your own private sanctuary among the lush landscape of Key West - envision old-fashioned screen-enclosed porc ...
From $1308 per night (USD)
Expedia
From $1426 per night (USD)
VRBO
Windward Point Beachfront Resort, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the glamour of this stylish, upscale place. Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the ...
From $1426 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Hyatt Windward Pointe, 2 Bedroom Waterfront Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Whether you choose to spend your days simply relaxing by the infinity pool or setting off on a dive adventure, Key West ...
From $416 per night (USD)
Expedia
From $826 per night (USD)
VRBO
Beach House Resort. Amenities Included Private Beach Area for Guests. 2BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience Key West Paradise at the Beach House Resort Retreat! Reservations at this property require owners to rent o ...
From $826 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Hyatt Beach House- On The Gulf With Private White Sand Beach - 2 Bedroom Villa!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Beach House! **Reservations are available in weekly (7 nigh ...
From $681 per night (USD)
Expedia
Click For Pricing
VRBO
Lush retreat minutes away from both Mallory Square & Duval Street.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
f bedrooms, full kitchen, screened in patio with a relaxing pool, and dock area perfect for sunset over the Gulf of Mexi ...
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VRBO
From $692 per night (USD)
Expedia
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 $692 per night (USD)
Expedia
Click For Pricing
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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VRBO
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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 ...
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Expedia
$Two Queen Beds w\/ Pool View & Terrace at The Gates Hotel Key West, Pet-Friendly!$
From $312 per night (USD)
VRBO
Two Queen Beds w\/ Pool View & Terrace at The Gates Hotel Key West, Pet-Friendly!
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 $312 per night (USD)
VRBO
From $2194 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 $2194 per night (USD)
Expedia

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Stock Island Rentals

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