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1524 Villa rentals in Key West, FL

Garden View And Olympic Pool - Charming Key West Sanctuary - Key West, FL
Key West, FL
4 2
$321/nighttotal: $3210 (10 )

Garden View And Olympic Pool - Charming Key West Sanctuary

house - Key West
This 2-bedroom, 2-bathroom condo in the 1800 Atlantic Condominiums complex is located 1.5 miles from downtown Key West and within walking distance of Smathers Beach, offering direct Atlantic Ocean access and a relaxing garden view overlooking a nature preserve.
This family-friendly accommodation sleeps up to 6 guests and features a full kitchen, air conditioning, a balcony, and access to shared amenities including a heated swimming pool, Jacuzzi, fitness center, and tennis courts.
The Contented Crane At Old Town - Key West, FL
9.9 357 reviews
Key West, FL
3 3
$2571/nighttotal: $12855 (5 )

The Contented Crane At Old Town

house - Key West
This Key West vacation home is located in the Historic District, just a short walk from Duval Street, the Hemingway House, and the Cemetery. The property has excellent ratings for location, cleanliness, and user experience.
The house has 6 bedrooms and can accommodate up to 8 guests. It features a private pool, a fully equipped kitchen, a patio for grilling, and free WiFi, making it perfect for families or groups of friends.
Dune Wind South By Avantstay - Key West, FL
Key West, FL
2 2
$380/nighttotal: $11400 (30 )

Dune Wind South By Avantstay

house - Key West
Dune Wind South, a Key West house rental, is located in a gated community less than two miles from Smathers Beach and within a three-mile radius of the Southernmost Point, Ernest Hemingway Home, and Duval Street.
This 1,100-square-foot property features two bedrooms, one bathroom, and accommodates up to seven guests, offering a private balcony, swimming pool, tennis court, and full kitchen with a dishwasher; month-long stays are required.
Corona At Azul Mansion Key West - Key West, FL
Key West, FL
2 1
$211/nighttotal: $422 (2 )

Corona At Azul Mansion Key West

B&B - Key West
CORONA at Azul Mansion, a Key West rental home, is conveniently located a 12-minute walk from South Beach, less than a mile from the Key West Aquarium and Mallory Square, and 0.4 miles from Key West's city center, placing you near Ernest Hemingway's Home and Museum and Duval Street.
This one-bedroom, one-bathroom house sleeps three guests and features a private pool, free Wi-Fi, on-site parking, and a terrace, providing easy access to Key West International Airport (1.9 miles away).
Paris Mango - Key West, FL
Key West, FL
4 4
$1048/nighttotal: $10480 (10 )

Paris Mango

house - Key West
Paris Mango is a residence located 1.2 miles from Key West International Airport, offering convenient access to attractions such as the Ernest Hemingway Home and Museum (2.3 miles), Duval Street (2.4 miles), and the Southernmost Point (2.6 miles).
This pet-friendly accommodation accommodates up to 15 guests with four bathrooms, a full kitchen featuring a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, spa, and a terrace or balcony, with complimentary WiFi and private parking provided.
Queen Of Louisa By Last Key Realty - Key West, FL
Key West, FL
5 4
$3615/nighttotal: $14460 (4 )

Queen Of Louisa By Last Key Realty

house - Key West
Queen of Louisa, a Key West vacation home, is located near South Beach (a 3-minute walk), Duval Street (0.5 miles), and the Ernest Hemingway Home and Museum (a 7-minute walk).
This 1,570-square-foot house features four bedrooms, four bathrooms, and accommodates up to 23 guests, offering a private pool, free Wi-Fi, and parking; nearby attractions include Fort Zachary Taylor State Park Beach and Higgs Beach.
Sailor's Son - Key West, FL
Key West, FL
2 4
$1851/nighttotal: $3702 (2 )

Sailor's Son

house - Key West
This Key West vacation home is situated 1.2 miles from the airport, with Duval Street and the Ernest Hemingway Home and Museum approximately 2.4 miles away.
This house accommodates up to 15 guests and features an outdoor swimming pool, hot tub, air conditioning, a well-equipped kitchen with a dishwasher, and private parking, with massage services offered by Sailor's Son.
Key Lime Hideaway - Key West, FL
Key West, FL
2 2
$460/nighttotal: $13800 (30 )

Key Lime Hideaway

house - Key West
This city center Key West house is located a short walk to South Beach and Duval Street, and 0.7 miles from the Ernest Hemingway Home and Museum.
This 1380 square foot vacation rental accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, plus complimentary WiFi and air conditioning.
Ocean View - Key West, FL
Key West, FL
4 2
$354/nighttotal: $3540 (10 )

Ocean View

house - Key West
This Key West vacation home, near Smathers Beach, offers stunning ocean views and is 1.6 miles from the Southernmost Point and 2.1 miles from the Ernest Hemingway Home and Museum.
This 1,310-square-foot property boasts two bedrooms, two bathrooms with a hot tub, a private balcony, a pool, a jacuzzi, and accommodates up to 11 guests, featuring a fully equipped kitchen and convenient in-house amenities including an elevator and ATM.
Kwss110 Sunrise Suites - Dominican Suite 110 - Key West, FL
8.0 1 review
Key West, FL
2 2
$631/nighttotal: $4417 (7 )

Kwss110 Sunrise Suites - Dominican Suite 110

house - Key West
This Dominican Suite 110 in Key West is located 0.6 miles from Key West International Airport and approximately 4 miles from Southernmost Point, Ernest Hemingway Home and Museum, and Duval Street.
This 800-square-foot condo accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, private balcony, and elevator access.
Driftwood Dreams By Last Key Realty - Key West, FL
Key West, FL
4 2
$273/nighttotal: $17199 (63 )

Driftwood Dreams By Last Key Realty

house - Key West
This Key West vacation home is a 4-minute walk from Smathers Beach, 1.6 miles from the Southernmost Point buoy, and 2 miles from the Ernest Hemingway Home and Museum.
This 1,360-square-foot property boasts two bedrooms, two bathrooms, and sleeps eleven, featuring a fully equipped kitchen, private parking, a pool, jacuzzi, spa, fitness center, and tennis court; enjoy sea views and free Wi-Fi.
Yellowfin Ledge - Key West, FL
10 4 reviews
Key West, FL
2 1
$693/nighttotal: $4851 (7 )

Yellowfin Ledge

house - Key West
This Key West vacation home, located on Yellowfin Ledge, is a short walk from South Beach and within a mile of Mallory Square, Duval Street, and the Ernest Hemingway Home and Museum.
The one-bedroom, one-bathroom rental offers a fully equipped kitchenette, sleeps five guests, and is conveniently located near Key West International Airport.

Browse Waterfront Vacation Homes in Key West, FL

Experience relaxing beach-town vibes at these seaside vacation homes in Key West, FL, located short distances from the local shore.

Blue Heron By Avantstay - Key West, FL
Key West, FL
2 2
$310/nighttotal: $9300 (30 )

Blue Heron By Avantstay

house - Key West
Blue Heron by AvantStay, a centrally located Key West house rental, is 0.4 miles from the city center, near the Ernest Hemingway Home and Museum, Duval Street, and Mallory Square.
This 650-square-foot property features two bedrooms, two bathrooms, a private pool, and accommodates up to seven guests, offering free Wi-Fi, a fully equipped kitchen with a dishwasher, and is a 12-minute walk from South Beach.

Search Vacation Homes with a Pool in Key West, FL

These Key West, FL vacation homes include a swimming pool, so a refreshing dip is always an option during your stay.

Brisa Fresca By Last Key Realty - Key West, FL
Key West, FL
4 3
$872/nighttotal: $54936 (63 )

Brisa Fresca By Last Key Realty

house - Key West
This Key West vacation home is less than a mile from Duval Street, an 8-minute walk from Fort Zachary Taylor State Park Beach, and a 15-minute walk from Simonton Street Beach.
This 1,750-square-foot house features three bedrooms, three bathrooms, a private pool, a fully equipped kitchen, free Wi-Fi, and parking; it comfortably sleeps 15 guests and offers access to nearby spa and tennis facilities.
Charming Townhome With Shared Pool And Balcony Views - Delightful Getaway - Key West, FL
Key West, FL
5 2
$535/nighttotal: $3745 (7 )

Charming Townhome With Shared Pool And Balcony Views - Delightful Getaway

house - Key West
This two-bedroom, two-bathroom townhome offers a prime location on the upper end of Duval Street in Key West, just steps from Southernmost Point and a short walk to the Key West Butterfly and Nature Conservatory.
This family-friendly rental sleeps up to six guests and features a king primary suite with a balcony, a second bedroom, a living room sofa bed, two balconies, access to a shared courtyard with a community pool, WiFi, Bose surround sound, and concierge services.
Pineapple Cottage - Top-rated Stay - Private Pool - 2bd/2.5bath - Key West, FL
10 242 reviews
Key West, FL
4 2
$2758/nighttotal: $8274 (3 )

Pineapple Cottage - Top-rated Stay - Private Pool - 2bd/2.5bath

cottage - Key West
The Pineapple Cottage is located in Key West's Old Town district, just a short walk from Duval Street and its lively atmosphere. This cottage has consistently received excellent reviews from previous guests.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy amenities like a private pool, a fully equipped kitchen, and a backyard oasis perfect for relaxing or grilling.
Charming Cottage With Private Deck And Beautiful Pool - Quaint Island Retreat - Key West, FL
Key West, FL
2 1
$408/nighttotal: $1632 (4 )

Charming Cottage With Private Deck And Beautiful Pool - Quaint Island Retreat

cottage - Key West
This Key West bungalow, part of The Colony, is located in Old Town, two blocks from Duval Street, offering an island hideaway.
This one-bedroom, one-bathroom cottage accommodates up to four guests and features a king-size bed, a full kitchen, air conditioning, and access to a shared swimming pool and garden.

Frequently Asked Questions about villa rentals in Key West, FL

  • What are the must-see attractions in Key West, FL?

    You can't miss the Southernmost Point Buoy, the iconic landmark marking the southernmost point of the continental US. The Ernest Hemingway Home and Museum is a must-visit for literature lovers, and you can't leave Key West without seeing the sunset at Mallory Square.
  • What are the best villa rentals in Key West, FL?

    Among the villa rentals in Key West, FL, Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas are the most popular ones.

  • What indoor activities for families are available in Key West, FL on rainy days?

    The Key West Aquarium is a great option for families, with exhibits showcasing local marine life. The Butterfly Conservatory at the Key West Botanical Garden is a beautiful and interactive experience, and the Mel Fisher Maritime Museum offers a fascinating glimpse into the history of shipwrecks.
  • What are the best villa rentals with a pool in Key West, FL?

    Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas are the best villa rentals with a pool in Key West, FL.

  • What are the best activities in Key West, FL?

    Key West is all about enjoying the water, so you can't go wrong with snorkeling, diving, or taking a sunset cruise. If you're looking for something more adventurous, try parasailing or jet skiing. And don't forget to relax on the beach and soak up the sun.
  • What are the best villa rentals with a jacuzzi in Key West, FL?

    The best villa rentals with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas.

  • What are the advantages of renting a house or a villa in Key West, FL

    Renting a house or villa in Key West gives you more space and privacy than a hotel. You'll also have access to a kitchen, laundry facilities, and often a private pool, which can be a big plus, especially for families or groups.
  • What are the best villa rentals for families and kids in Key West, FL?

    The best villa rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas.

  • What food festivals or culinary events take place in and around Key West, FL?

    Key West is known for its vibrant food scene, and there are several festivals and events throughout the year. The Key West Food & Wine Festival is a highlight, featuring tastings, cooking demonstrations, and more. You can also check out the Key West Lobsterfest and the Key West Seafood Festival.
  • What are the best pet friendly villa rentals in Key West, FL?

    The best pet friendly villa rentals in Key West, FL are Leaward Isle Island Retreat, Secret Courtyard Cottage and Pescado Penthouse On Duval.

  • What exclusive experiences are available when visiting Key West, FL?

    For a truly unique experience, take a sunset sail on a historic schooner or enjoy a private dinner on the beach. You can also book a private fishing charter or go on a guided kayak tour through the mangroves.
  • What are the best villa rentals with parking in Key West, FL?

    Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas are the best villa rentals with parking in Key West, FL.

  • Which part of Key West, FL would be ideal for a villa rental?

    The Old Town area is popular for its historic charm and proximity to attractions. If you prefer a quieter location, consider renting a villa in the New Town area or on the waterfront.

Popular destinations

Best Key West, FL villas and beach houses with jacuzzi

Atlantic Paradise Found - Key West, FL
9.6 234 reviews
Key West, FL
2 2
$1087/nighttotal: $7609 (7 )

Atlantic Paradise Found

house - Key West
This Key West rental is just a short walk from Smathers Beach, one of the most popular beaches in Key West, and within easy reach of other attractions like Higgs Beach and Southernmost Point. It has excellent ratings for location, cleanliness, and user experience.
This two-bedroom apartment offers 1360 square feet of space, comfortably accommodating up to six guests. You'll enjoy a fully equipped kitchen, a private balcony with stunning ocean views, a swimming pool, a jacuzzi, a fitness center, and a tennis court.
Casa Riviera Waterfront Hacienda With Pool And Boat Lift - Key West, FL
Key West, FL
2 3
$1191/nighttotal: $35730 (30 )

Casa Riviera Waterfront Hacienda With Pool And Boat Lift

house - Key West
This Key West waterfront hacienda is located 2.6 miles from the Southernmost Point and 1.2 miles from Key West International Airport, with convenient access to Duval Street and Mallory Square.
This 2100 sq ft home accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a private swimming pool, hot tub, boat elevator, full kitchen, and free WiFi.
Atlantic Paradise By Avantstay - Key West, FL
9.4 140 reviews
Key West, FL
2 2
$576/nighttotal: $1152 (2 )

Atlantic Paradise By Avantstay

house - Key West
Located in the peaceful Beachside district of Key West, this vacation home offers a tranquil retreat just steps from Florida Keys Beaches and a short drive from Duval Street and Mallory Square. With excellent user, location, and cleanliness ratings, it promises a comfortable and memorable stay.
The vacation home features two private bedrooms and a well-equipped kitchen, accommodating up to six guests in its 1360 square feet of space. Amenities include a fitness center, spa tub, free Wi-Fi, and a private terrace or balcony. Guests can also enjoy the lush garden, swimming pool, Jacuzzi, tennis court, and ample parking.
Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok - Key West, FL
9.2 100 reviews
Key West, FL
2 4
$1201/nighttotal: $2402 (2 )

Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok

cabin - Key West
This pair of cottages is located in Old Town Key West, half a block from Duval Street, and within walking distance of the Key West Lighthouse, The Ernest Hemingway Home and Museum, and Southernmost Point.
This dog-friendly vacation rental offers 1630 square feet of space, accommodating up to 12 guests with 4 bedrooms and 2 bathrooms, and features a private hot tub and a full kitchen.

Neighborhoods and points of interest in Key West, FL

Best Key West, FL houses with a kitchen

Egret Suite - Southernmost Sanctuary - Key West, FL
10 2 reviews
Key West, FL
2 1
$341/nighttotal: $682 (2 )

Egret Suite - Southernmost Sanctuary

house - Key West
The Egret Suite is located in Key West's southernmost area, a short walk from South Beach and less than a mile from Duval Street and the Ernest Hemingway Home and Museum.
This one-bedroom, one-bathroom Key West house rental sleeps seven guests and features a fully equipped kitchen, free Wi-Fi, air conditioning, and a terrace; nearby beaches include Higgs Beach and Rest Beach.
127 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 30 reviews
Key West, FL
4 2
$1591/nighttotal: $4773 (3 )

127 M² House ∙ 2 Bedrooms ∙ 6 Guests

house - Key West
This Old Town Key West home, four blocks from the Atlantic Ocean and one block from Duval Street, offers easy access to Key West's renowned nightlife and beaches.
This 1,370-square-foot house features two bedroom suites, a private pool (with optional heating), a full kitchen, and can comfortably accommodate up to six guests.
123 M² House ∙ 3 Bedrooms ∙ 7 Guests - Key West, FL
10 2 reviews
Key West, FL
4 3
$203/nighttotal: $12789 (63 )

123 M² House ∙ 3 Bedrooms ∙ 7 Guests

house - Key West
This spacious townhome is located in Key West Golf Club, a private gated community, offering views of the 15th fairway and lakes, just minutes from Key West beaches, restaurants, and water sports.
This 1320 square feet residence accommodates up to 7 guests with 3 bedrooms and 3 bathrooms, featuring a fully appointed kitchen, two screened verandas, a fenced backyard with a Weber Grill, a swimming pool, and a fitness center.
Old Town Getaway - Key West, FL
Key West, FL
4 1
$403/nighttotal: $25389 (63 )

Old Town Getaway

house - Key West
Old Town Getaway, a one-bedroom Key West vacation rental, is conveniently located in Old Town, a six-minute walk from Duval Street, seventeen minutes from Mallory Square, and fourteen minutes from South Beach.
This 610-square-foot house sleeps seven guests and features a fully equipped kitchen with a dishwasher, free Wi-Fi, a washer, and air conditioning.

Guest-Favorite Luxury Vacation Homes in Key West, FL

These upscale vacation homes in Key West, FL provide the perfect blend of premium amenities and a highly desirable prime location.

Florida - Spacious Updated Waterfront Condo 2x2 Pool Dock - Key West, FL
9.0 2 reviews
Key West, FL
3 2
$1391/nighttotal: $6955 (5 )

Florida - Spacious Updated Waterfront Condo 2x2 Pool Dock

house - Key West

Choose the Right Family-Friendly Holiday Houses in Key West, FL

Choosing a family vacation home in Key West, FL provides plenty of room to spread out and the perfect space to plan your day with the kids.

Valhalla - Southernmost Oasis - Key West, FL
Key West, FL
2 2
$1983/nighttotal: $13881 (7 )

Valhalla - Southernmost Oasis

house - Key West
102 M² House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
Key West, FL
2 2
$310/nighttotal: $9300 (30 )

102 M² House ∙ 2 Bedrooms ∙ 4 Guests

house - Key West
Stunning Pool And Unique Design - Captivating Modern Retreat - Key West, FL
Key West, FL
4 4
$3103/nighttotal: $6206 (2 )

Stunning Pool And Unique Design - Captivating Modern Retreat

house - Key West
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.4 20 reviews
Key West, FL
2 2
$839/nighttotal: $11746 (14 )

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

house - Key West

Find the Best Pet-Friendly Vacation Homes in Key West, FL

Traveling with your dog? These Key West, FL vacation homes are pet-ready, so you and your four-legged companion can relax from the moment you arrive.

Kingfish Keep - Key West, FL
9.0 2 reviews
Key West, FL
2 1
$733/nighttotal: $10262 (14 )

Kingfish Keep

house - Key West
The Dancing Rooster: 2 Blocks From Duval In Old Town. - Key West, FL
9.8 150 reviews
Key West, FL
4 3
$933/nighttotal: $1866 (2 )

The Dancing Rooster: 2 Blocks From Duval In Old Town.

cottage - Key West
St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet - Key West, FL
9.2 10 reviews
Key West, FL
3 4
$1392/nighttotal: $2784 (2 )

St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet

house - Key West
Swept Away By Last Key Realty - Key West, FL
Key West, FL
2 2
$629/nighttotal: $18870 (30 )

Swept Away By Last Key Realty

house - Key West

Explore Holiday Houses with Wellness in Key West, FL

Discover spa access at these waterfront vacation homes in Key West, FL, ensuring wellness by the water is never an afterthought.

Coconut Cabana - Key West, FL
Key West, FL
2 3
$1682/nighttotal: $6728 (4 )

Coconut Cabana

house - Key West

Best Key West, FL houses with air conditioning

Two Duval Street Condos W Parking And Pool - Key West, FL
9.9 1093 reviews
Key West, FL
2 1
$456/nightfor 1 night

Two Duval Street Condos W Parking And Pool

house - Key West
St John - Downtown Waterfront Penthouse Pool Parking Dock - Key West, FL
9.3 3 reviews
Key West, FL
2 4
$2837/nighttotal: $19859 (7 )

St John - Downtown Waterfront Penthouse Pool Parking Dock

house - Key West
Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo - Key West, FL
9.1 18 reviews
Key West, FL
3 2
$555/nighttotal: $1110 (2 )

Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo

house - Key West
Kw33b Windward Isle - Key West, FL
Key West, FL
4 2
$907/nighttotal: $2721 (3 )

Kw33b Windward Isle

house - Key West
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