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Results: 489 Rentals

  • Tropical Paradise set along the Atlantic Ocean minutes to Old Town Key West.
    From $910 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 $910 per night (USD)

    VRBO

    Details
  • WATER FRONT LOCATION WITH GREAT LOCATION TO KEY WEST.
    From $448 per night (USD)

    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 ...

    From $448 per night (USD)

    Expedia

    Details
  • Hyatt Beach House Resort, Key West, Florida - FANTASY FEST WEEK 2023
    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. ...

    Click For Pricing

    VRBO

    Details
  • A Poolside Cabana at the Key West Golf Club!
    From $325 per night (USD)

    Expedia

    A Poolside Cabana at the Key West Golf Club!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...

    From $325 per night (USD)

    Expedia

    Details
  • Boater’s Paradise
    From $550 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 $550 per night (USD)

    VRBO

    Details
  • Gone Coastal
    From $462 per night (USD)

    Expedia

    Gone Coastal

    Bedrooms:
    2
    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 $462 per night (USD)

    Expedia

    Details
  • KEY WEST PARADISE- YOUR HAPPY PLACE
    Click For Pricing

    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 ...

    Click For Pricing

    VRBO

    Details
  • Dog-friendly, Gulf-front condo with pool, hot tub & gorgeous sunset views
    From $285 per night (USD)

    Expedia

    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 $285 per night (USD)

    Expedia

    Details
  • Parking, Pet Friendly, Pool - Crestwood House
    From $2506 per night (USD)

    VRBO

    Parking, Pet Friendly, Pool - Crestwood House

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Summary: This stunning 6-bedroom, 6.5-bath home offers the perfect Key West getaway with a private pool, fire pit, parki ...

    From $2506 per night (USD)

    VRBO

    Details
  • Fantasy Fest Week!! Spacious 2-Bedroom Suite Hyatt Windward Point
    Click For Pricing

    Expedia

    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 Pricing

    Expedia

    Details
  • Colorful home in private community with resort pool & hot tub, on-site golf
    From $166 per night (USD)

    VRBO

    Colorful home in private community with resort pool & hot tub, on-site golf

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Egret House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...

    From $166 per night (USD)

    VRBO

    Details
  • Hyatt Vacation Club Windward Pointe Key West. Spectacular Key West Ocean Resort
    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

    Details
  • Parking, Heated Pool & Pet Friendly - Altair House
    From $2440 per night (USD)

    VRBO

    Parking, Heated Pool & Pet Friendly - Altair House

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Summary: This beautifully designed 6-bedroom, 6.5-bath home is your perfect Key West retreat. Relax with a private pool, ...

    From $2440 per night (USD)

    VRBO

    Details
  • New Listing-Golf Course Charmer!
    Click For Pricing

    Expedia

    New Listing-Golf Course Charmer!

    Bedrooms:
    1
    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 ...

    Click For Pricing

    Expedia

    Details
  • Private & Haven-ly pool home on boating canal
    Click For Pricing

    VRBO

    Private & Haven-ly pool home on boating canal

    Bedrooms:
    2
    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 ...

    Click For Pricing

    VRBO

    Details
  • **KESTRAL KOVE @ THE GOLF CLUB** Townhome w/ Community Pool + LAST KEY SERVICES…
    Click For Pricing

    Expedia

    **KESTRAL KOVE @ THE GOLF CLUB** Townhome w/ Community Pool + LAST KEY SERVICES…

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Dreaming of va ...

    Click For Pricing

    Expedia

    Details
  • SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
    Click For Pricing

    VRBO

    SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    You and your guests will have exclusive use of this 45 ft yacht all to yourselves. The yacht stays docked, the entire re ...

    Click For Pricing

    VRBO

    Details
  • **THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
    From $363 per night (USD)

    Expedia

    **THE OSPREY'S NEST @ 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! Want to be in ...

    From $363 per night (USD)

    Expedia

    Details
  • Luxury Home w/ Heated Pool - The Windrose Estate
    From $2408 per night (USD)

    VRBO

    Luxury Home w/ Heated Pool - The Windrose Estate

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Summary: This newly designed 6 bedroom, 6 bath home is perfect for those looking to embrace all that Key West has to off ...

    From $2408 per night (USD)

    VRBO

    Details
  • Luxury Home with Heated Pool - The Ebberly Estate
    From $2422 per night (USD)

    Expedia

    Luxury Home with Heated Pool - The Ebberly Estate

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Summary: Welcome to your dream escape in Key West! This luxurious 6-bedroom, 6.5-bath home combines elegance and island ...

    From $2422 per night (USD)

    Expedia

    Details
  • Coconut Mallory Resort in Key West - 2 Bedroom Condo/Marina/Gumbos Bar & Grill
    Click For Pricing

    VRBO

    Coconut Mallory Resort in Key West - 2 Bedroom Condo/Marina/Gumbos Bar & Grill

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Coconut Mallory Resort and Marina in Key West 2 Bedroom 2 Bath Condo partial fantasy fest 10/28/23 - 11/4-23 (Saturday t ...

    Click For Pricing

    VRBO

    Details
  • Poolside tropical paradise in Key West! The Salty Conch
    From $227 per night (USD)

    Expedia

    Poolside tropical paradise in Key West! The Salty Conch

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    The Salty Conch is tucked away in the gated community of The Key West Golf Club with 24/7 security for your peace of min ...

    From $227 per night (USD)

    Expedia

    Details
  • Uptown quiet cottage close to beaches, restaurant & shopping.
    From $120 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 $120 per night (USD)

    VRBO

    Details
  • INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
    From $451 per night (USD)

    Expedia

    INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    NESTLED IN THE HEART OF PARADISE… Stunning views of the ocean and nature surround you in this lovely getaway. Your soul ...

    From $451 per night (USD)

    Expedia

    Details
  • HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
    From $313 per night (USD)

    VRBO

    HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A SIMPLE GETAWAY… If you are craving a simple yet sensational taste of paradise, look no further. This small but mighty ...

    From $313 per night (USD)

    VRBO

    Details
  • ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
    From $372 per night (USD)

    Expedia

    ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A TRANQUIL GETAWAY FOR 6… Welcome to captivating views of the ocean ideal for unwinding and unpluging from reality. You ...

    From $372 per night (USD)

    Expedia

    Details
  • Living the Dream Key West Style
    From $336 per night (USD)

    VRBO

    Living the Dream Key West Style

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Reconnect with nature at this unforgettable escape. Experience and enjoy what life is like living on a large world cruis ...

    From $336 per night (USD)

    VRBO

    Details
  • Craig & Cindy Key West Poolside Coral Hammock Royal Palm House 2 bdrm 2.5 bath
    From $369 per night (USD)

    Expedia

    Craig & Cindy Key West Poolside Coral Hammock Royal Palm House 2 bdrm 2.5 bath

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Coral Hammock is a gated communities with 55 luxury resort homes with a lavish Clubhouse and Pool and lushly landscaped ...

    From $369 per night (USD)

    Expedia

    Details
  • **THE LARK’S LANDING @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
    From $353 per night (USD)

    VRBO

    **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 $353 per night (USD)

    VRBO

    Details
  • LAST MINUTE: 2BR Condo Key West for championship boat races!
    Click For Pricing

    Expedia

    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 ...

    Click For Pricing

    Expedia

    Details
  • Beautiful Houseboat in Key West
    From $745 per night (USD)

    VRBO

    Beautiful Houseboat in Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy this classic floating home all to yourself! This home can accommodate up to four guests and has two bedrooms and o ...

    From $745 per night (USD)

    VRBO

    Details
  • Spacious Key West Condo at Coconut Mallory Resort & Marina
    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

    Details
  • 2/2 Timeshare Rental - Only Available 12/19  to 12/22  and 12/29 to 12/30/2024
    Click For Pricing

    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 ...

    Click For Pricing

    VRBO

    Details
  • Decorators own Coastal Chic home
    From $546 per night (USD)

    VRBO

    Decorators own Coastal Chic home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    BRAND NEW, Coastal on Coral is located in the beautiful gated community of Coral Hammock on the quiet end of Key West on ...

    From $546 per night (USD)

    VRBO

    Details
  • Beautiful 2 Bedroom, 2 Bath Condo Resort on the Ocean in Key West. \n
    Click For Pricing

    VRBO

    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 ...

    Click For Pricing

    VRBO

    Details
  • Studio with kitchenette, free parking, marina available 3/12/22 to 3/19/22 only<br>
    Click For Pricing

    Expedia

    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 ...

    Click For Pricing

    Expedia

    Details
  • Hyatt Windward Pointe, 2 Bedroom Waterfront Condo
    From $416 per night (USD)

    VRBO

    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)

    VRBO

    Details
  • Beach House Resort. Amenities Included Private Beach Area for Guests. 2BR Condo
    From $919 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 $919 per night (USD)

    VRBO

    Details
  • Newly Renovated  condo with scenic views, pool & hot tub, balcony, & parking
    From $348 per night (USD)

    VRBO

    Newly Renovated condo with scenic views, pool & hot tub, balcony, & parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Sunrise Suites - Saint Kitts 412 Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...

    From $348 per night (USD)

    VRBO

    Details
  • Hyatt Windward Pointe 2 bdrm 2 ba full kitch view\n
    From $753 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 $753 per night (USD)

    Expedia

    Details
  • Sunrise 308-2BR/2BA condo near beaches with pool, parking, balcony
    From $395 per night (USD)

    VRBO

    Sunrise 308-2BR/2BA condo near beaches with pool, parking, balcony

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $395 per night (USD)

    VRBO

    Details
  • Coconut Cottage Sunset Marina-2bed 2bath oceanfront condo w/pool, dock space
    From $252 per night (USD)

    Expedia

    Coconut Cottage Sunset Marina-2bed 2bath oceanfront condo w/pool, dock space

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $252 per night (USD)

    Expedia

    Details
  • Hyatt Beach House Resort Key West 1-7 nights
    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

    Details
  • Private Pool, Outdoor Shower, Pet Friendly, in Golf Course- 5 min to Beach
    From $410 per night (USD)

    VRBO

    Private Pool, Outdoor Shower, Pet Friendly, in Golf Course- 5 min to Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Livin' On Key West Time Vacation Rental! This 2-bed 2-bath townhome is located in the prestigious Key West Go ...

    From $410 per night (USD)

    VRBO

    Details
  • 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beach House Resort + Amenities, 2-Bedroom
    From $1192 per night (USD)

    VRBO

    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 $1192 per night (USD)

    VRBO

    Details
  • Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!
    From $575 per night (USD)

    Expedia

    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 $575 per night (USD)

    Expedia

    Details
  • Living Life Dockside
    From $472 per night (USD)

    VRBO

    Living Life Dockside

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Take it easy at this unique and tranquil getaway located right on the water in a beautifully artistic and tropical lands ...

    From $472 per night (USD)

    VRBO

    Details
  • 3 BR 2BA + Private Pool + Waterfront
    From $710 per night (USD)

    Expedia

    3 BR 2BA + Private Pool + Waterfront

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Beach Weekend invites you to experience the ultimate getaway at Key Haven Oasis! Unlock 10% off a pontoon renta ...

    From $710 per night (USD)

    Expedia

    Details
  • Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
    From $484 per night (USD)

    VRBO

    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)

    VRBO

    Details
  • Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
    From $380 per night (USD)

    Expedia

    Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...

    From $380 per night (USD)

    Expedia

    Details
  • Prime Tee Haven | 2 bed/2.5 bath townhouse on golf course with shared pool
    From $262 per night (USD)

    VRBO

    Prime Tee Haven | 2 bed/2.5 bath townhouse on golf course with shared pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Indulge in the ultimate getaway experience with our stunning 2 bedroom, 2 1/2 bathroom townhouse nestled on the pictures ...

    From $262 per night (USD)

    VRBO

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $782 per night (USD)

    Expedia

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $782 per night (USD)

    Expedia

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $729 per night (USD)

    VRBO

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $729 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1002 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1002 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $997 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $997 per night (USD)

    VRBO

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $784 per night (USD)

    Expedia

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $784 per night (USD)

    Expedia

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $749 per night (USD)

    VRBO

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $749 per night (USD)

    VRBO

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $905 per night (USD)

    Expedia

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $905 per night (USD)

    Expedia

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $808 per night (USD)

    VRBO

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $808 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $865 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $865 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $929 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $929 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $923 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $923 per night (USD)

    Expedia

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $808 per night (USD)

    VRBO

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $808 per night (USD)

    VRBO

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $905 per night (USD)

    Expedia

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $905 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1006 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1006 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $876 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $876 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1006 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1006 per night (USD)

    VRBO

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $826 per night (USD)

    Expedia

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $826 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $866 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $866 per night (USD)

    VRBO

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $803 per night (USD)

    Expedia

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $803 per night (USD)

    Expedia

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $805 per night (USD)

    VRBO

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $805 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $875 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $875 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $601 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $601 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $594 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $594 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $567 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $567 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $678 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $678 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $592 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $592 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $604 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $604 per night (USD)

    Expedia

    Details
  • Two Bedroom Residence
    From $590 per night (USD)

    VRBO

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $590 per night (USD)

    VRBO

    Details
  • Two Bedroom Residence
    From $589 per night (USD)

    Expedia

    Two Bedroom Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $589 per night (USD)

    Expedia

    Details
  • Pool View 3BR Residence | Beachside Resort
    From $764 per night (USD)

    VRBO

    Pool View 3BR Residence | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $764 per night (USD)

    VRBO

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $868 per night (USD)

    Expedia

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $868 per night (USD)

    Expedia

    Details
  • Ocean Front Presidential Suite | Beachside Resort
    From $1006 per night (USD)

    VRBO

    Ocean Front Presidential Suite | Beachside Resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residenc ...

    From $1006 per night (USD)

    VRBO

    Details
  • Sunrise 307-2BR/2BA condo near beaches with pool, parking, balcony
    From $418 per night (USD)

    Expedia

    Sunrise 307-2BR/2BA condo near beaches with pool, parking, balcony

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $418 per night (USD)

    Expedia

    Details
  • Reduced Rate! 46’ Yacht in Beautiful Resort!
    Click For Pricing

    VRBO

    Reduced Rate! 46’ Yacht in Beautiful Resort!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    New Listing on VRBO! You and your guests will have exclusive use of this 46 ft yacht all to yourselves. The yacht stays ...

    Click For Pricing

    VRBO

    Details
  • Triple Crown Villa- Boaters Paradise with Pool
    From $616 per night (USD)

    Expedia

    Triple Crown Villa- Boaters Paradise with Pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    If you're looking for a luxurious and unforgettable waterfront vacation experience, look no further than this stunning v ...

    From $616 per night (USD)

    Expedia

    Details
  • Ready II Play: Luxury Motor Yacht
    From $1770 per night (USD)

    VRBO

    Ready II Play: Luxury Motor Yacht

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Welcome aboard Motor Yacht Ready II Play, a 115-foot luxury vessel offering a unique and unforgettable vacation experien ...

    From $1770 per night (USD)

    VRBO

    Details
  • Gorgeous Waterfront Home - Haven House
    From $353 per night (USD)

    Expedia

    Gorgeous Waterfront Home - Haven House

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Summary: The Haven House is truly heavenly on the quiet residential canals in Key Haven. This home boasts a modern water ...

    From $353 per night (USD)

    Expedia

    Details
  • Waterfront & Heated Pool - Awai's Floating Villa
    From $818 per night (USD)

    VRBO

    Waterfront & Heated Pool - Awai's Floating Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience Key West in a new way: aboard a luxury houseboat! From watching sunrise on the dock to watching suns ...

    From $818 per night (USD)

    VRBO

    Details
  • Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n
    From $1122 per night (USD)

    Expedia

    Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom ...

    From $1122 per night (USD)

    Expedia

    Details
  • Last Mango Beach Retreat
    From $404 per night (USD)

    VRBO

    Last Mango Beach Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the allure of La Brisa Penthouse! Step into this captivating two-bedroom, two-bathroom condo nestled within t ...

    From $404 per night (USD)

    VRBO

    Details
  • Key Haven 3bedroom 2bath canal front home w/boat dock, private pool, parking
    From $299 per night (USD)

    Expedia

    Key Haven 3bedroom 2bath canal front home w/boat dock, private pool, parking

    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 $299 per night (USD)

    Expedia

    Details
  • Escape to \Oasis on 18th\ w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!
    From $354 per night (USD)

    VRBO

    Escape to \"Oasis on 18th\" w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...

    From $354 per night (USD)

    VRBO

    Details
  • Key West - Stock Island
    From $352 per night (USD)

    Expedia

    Key West - Stock Island

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Two Bedroom and 2 and Half Bath beautiful condo in great private Coral Hammock community, close to Golf Course and short ...

    From $352 per night (USD)

    Expedia

    Details
  • Seaside Serenity-2BD 2BA condo w/ pool, parking, tennis courts, near beaches
    From $236 per night (USD)

    VRBO

    Seaside Serenity-2BD 2BA condo w/ pool, parking, tennis courts, near beaches

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...

    From $236 per night (USD)

    VRBO

    Details
  • Hyatt Windward Pointe 2BR in Key West 6/22/2024 to 6/29/2024 for 7 nights
    Click For Pricing

    Expedia

    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 Pricing

    Expedia

    Details
  • Windward Point Beachfront Resort, Hot Tub, Pool
    From $1664 per night (USD)

    VRBO

    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 $1664 per night (USD)

    VRBO

    Details
  • Windward Point Beachfront Resort, Hot Tub, Pool
    From $1262 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 $1262 per night (USD)

    VRBO

    Details
  • Mallory Resort, Beach, Hot Tub, Pool, BBQ, Marina
    From $1545 per night (USD)

    VRBO

    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)

    VRBO

    Details
  • Oceans Edge Key West Resort, Hotel & Marina!
    From $1424 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 $1424 per night (USD)

    VRBO

    Details