Holiday Rentals in Key West, FL

3183 available vacation rental offers

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Key West, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Key West, FL

Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval! - Key West, FL
9.6 40 reviews
Key West, FL
30/07 – 02/08
£201/nighttotal: £603 (3 )

Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval!

1 4
apartment, Key West
Located in Old Town Key West, this apartment is just steps from Duval Street, 160 meters from the Southernmost Point, and 480 meters from South Beach.
This pet-friendly apartment, accommodating up to four guests, features a kitchenette, air conditioning, and access to shared hot tubs and a communal patio.
The Coral Cottage In Historic Key West - Key West, FL
10 6 reviews
Key West, FL
01/07 – 31/08
£133/nighttotal: £8113 (61 )

The Coral Cottage In Historic Key West

2 2
apartment, Key West
Authentically experience a historic Conch home in a local Key West neighbourhood, just 800 meters from nearby beaches, parks, and cafes, offering a truly dog-friendly stay.
This renovated apartment boasts a private porch with seating and a grill, a full suite of stainless steel appliances, and provides access to a pool at a sister property, accommodating up to four guests and one pet.
Ibis Suite - Southernmost Sanctuary - Key West, FL
8.6 5 reviews
Key West, FL
08/06 – 10/06
£244/nighttotal: £488 (2 )

Ibis Suite - Southernmost Sanctuary

1 2
house, Key West
Just a few steps from South Beach, this pet-friendly house is located 0.8 kilometres from Key West's city centre, offering immediate coastal access and proximity to Mallory Dock and Mallory Square.
This air-conditioned house, featuring a kitchen with a fridge and microwave, welcomes pets and provides towels and bed linen for up to 7 guests across 37 square metres with 1 bedroom.
Heron Suite | Vibrant Retreat, Hot Tub, Near Duval - Key West, FL
9.4 7 reviews
Key West, FL
19/07 – 21/07
£220/nighttotal: £440 (2 )

Heron Suite | Vibrant Retreat, Hot Tub, Near Duval

1 4
apartment, Key West
Ideally located in the Duval Street district, this apartment is just steps from the street itself, 160 meters from the Southernmost Point, and 480 meters from South Beach.
This pet-friendly apartment allows one small dog for an extra fee and offers a kitchenette, air conditioning, and access to shared hot tubs and laundry facilities, sleeping up to four guests.
Poolside Paradise @ Tropical Village By Rent Key - Key West, FL
9.4 17 reviews
Key West, FL
30/05 – 06/06
£220/nighttotal: £1540 (7 )

Poolside Paradise @ Tropical Village By Rent Key

1 2
apartment, Key West
Located in Key West's historic Casa Marina Neighbourhood, this apartment is just 2 blocks from Higgs Beach and a short walk to attractions such as the KW Butterfly and Nature Museum and Southernmost Point.
This pet-friendly one-bedroom apartment offers a cosy kitchenette, private patio dining, and access to shared amenities including a swimming pool and gas grill, making it ideal for travellers with pets.
Vangogh Studio | Updated, Old Town, Heated Pool - Key West, FL
8.6 45 reviews
Key West, FL
08/06 – 10/06
£194/nighttotal: £388 (2 )

Vangogh Studio | Updated, Old Town, Heated Pool

1 2
studio, Key West
Located in Old Town Key West's Bahama Village, this studio is a short 800-metre stroll from Duval Street and within walking distance of the Southernmost Point and Ernest Hemingway Home.
This pet-friendly studio offers a well-appointed kitchenette, air conditioning, and access to a heated swimming pool, perfect for guests travelling with their dog.
Conch Key - Monthly Rental - Key West, FL
Key West, FL
13/12 – 10/01
£414/nighttotal: £11592 (28 )

Conch Key - Monthly Rental

2 3
house, Key West
Located in Conch Key, this house is an 8-minute walk to Rest Beach and 1.2 kilometres from Southernmost Point, with Key West International Airport also 1.2 kilometres away.
This pet-friendly house offers 2 bedrooms, 2 bathrooms, air conditioning, a private swimming pool, and a fully equipped kitchen, perfect for accommodating up to 7 guests.
Atocha Cottage At Harbor Walk Hideaways | Old Town - Key West, FL
9.8 13 reviews
Key West, FL
14/07 – 16/07
£348/nighttotal: £696 (2 )

Atocha Cottage At Harbor Walk Hideaways | Old Town

2 5
apartment, Key West
This pet-friendly apartment in Key West's Historic Seaport district is just 200 meters from the waterfront and Mallory Square's sunset celebrations, offering immediate proximity to dining and nightlife.
With two bedrooms and a guest capacity of six, this accommodation provides Tempur-Pedic mattresses, free Wi-Fi, a mini fridge, microwave, Keurig coffee maker, and access to a shared dipping pool with a waterfall feature.
Lilly’s Cottage - Key West, FL
10 3 reviews
Key West, FL
01/07 – 31/07
£109/nighttotal: £3270 (30 )

Lilly’s Cottage

1 2
apartment, Key West
Centrally located in Old Town Key West, this apartment is a short walk to Duval Street and a local grocery store, with a fishing pier nearby.
This pet-friendly apartment boasts an outdoor fenced area and air conditioning, perfect for two guests seeking a 28-night minimum stay in Key West.
The Curry Poolside | Ground  Floor King - Key West, FL
9.4 27 reviews
Key West, FL
30/05 – 06/06
£221/nighttotal: £1547 (7 )

The Curry Poolside | Ground Floor King

1 2
apartment, Key West
Situated in the Key West Historic District, this apartment is just 100 meters from Duval Street and within easy walking distance of the Historic Seaport and Mallory Square.
This pet-friendly apartment offers a shared heated swimming pool, a terrace and air conditioning, perfect for a couple visiting Key West.
Abbey's Attic - Truman @ Duval Unit E - Key West, FL
Key West, FL
30/05 – 06/06
£178/nighttotal: £1246 (7 )

Abbey's Attic - Truman @ Duval Unit E

1 2
apartment, Key West
Just 300 metres from Key West city centre, this apartment is ideally situated for exploring the area, being a mere 7-minute walk to South Beach and 0.9 miles from Mallory Dock.
This pet-friendly apartment offers accommodation for up to 3 guests, featuring air conditioning, a separate bedroom, a bathroom, and a kitchenette with a microwave and fridge, making it a convenient choice for travellers with pets.
Blue Flamingo Resort Key West - Key West, FL
Key West, FL
14/06 – 16/06
£117/nighttotal: £234 (2 )

Blue Flamingo Resort Key West

1 1
resort, Key West
Located 5 kilometres from Key West city centre, Blue Flamingo Resort Key West offers a pet-friendly escape near the Key West Tropical Forest and Botanical Garden.
This resort boasts multiple swimming options, on-site dining with live music, a fitness centre, and tour assistance, ensuring a comfortable stay for guests and their dogs.

Best Key West, FL holiday rentals with parking

In Key West, FL, finding dog-friendly vacation rentals with parking makes your trip seamless. Whether you prefer the comfort of a unique hotel or seek affordable alternatives to budget friendly hotels, these options ensure convenience for both you and your pet.

Opal Key Resort & Marina - Key West, FL
9.0 100 reviews
Key West, FL
30/05 – 06/06
£284/nighttotal: £1988 (7 )

Opal Key Resort & Marina

1 2
resort, Key West
Perfectly situated, Opal Key Resort & Marina in Key West is a mere 500 metres from Mallory Square and a 3-minute walk to Duval Street, offering a prime location for exploring the city and is also 0.5 kilometres from Florida Keys Beaches and 0.7 kilometres from the Ernest Hemingway Home and Museum.
This pet-friendly resort boasts an outdoor pool and a 24-hour fitness centre, with rooms featuring flat-screen TVs and rainfall showerheads, ensuring a comfortable stay for you and your dog-friendly companions.
Rose Lane Villas - Key West, FL
9.0 931 reviews
Key West, FL
01/06 – 02/06
£393/nightfor 1 night

Rose Lane Villas

2 4
house, Key West
Perfectly situated just off Duval Street in Key West, Florida, this house is a mere 1.1 kilometers from the Southernmost Point and a convenient 5-minute walk to the Key West Aquarium, with the Ernest Hemingway Home and Museum only 0.9 miles away.
This pet-friendly house offers a heated outdoor swimming pool and fully equipped kitchens, alongside free Wi-Fi, ensuring a comfortable stay for you and your dog-friendly companion.
Waterfront Condo Dock Pool Downtown Near Duval - Key West, FL
9.6 29 reviews
Key West, FL
14/07 – 16/07
£603/nighttotal: £1206 (2 )

Waterfront Condo Dock Pool Downtown Near Duval

2 5
apartment, Key West
This pet-friendly apartment in historic Downtown Key West is less than 1.6 kilometers from Duval Street, the Historic Seaport, and the Hemingway House, offering easy walkability to major attractions.
Boasting 121 square meters of space, this apartment sleeps up to 8 guests with 2 bedrooms and 2 bathrooms, featuring a fully stocked kitchen, a private balcony overlooking the marina and heated pool, and on-site parking.
Claude Monet Suite | Cozy Studio With Pool & Patio - Key West, FL
9.6 34 reviews
Key West, FL
19/07 – 21/07
£220/nighttotal: £440 (2 )

Claude Monet Suite | Cozy Studio With Pool & Patio

1 4
studio, Key West
Located in Bahama Village, this studio is just a few blocks from Duval Street and within walking distance of the Southernmost Point and Hemingway House.
This pet-friendly studio, measuring 24 square meters, offers a Queen bed, a full-size sleeper sofa, and a kitchenette, with a heated swimming pool and sundeck available for guests.
Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking - Key West, FL
8.9 189 reviews
Key West, FL
19/07 – 21/07
£370/nighttotal: £740 (2 )

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

2 4
house, Key West
Located in Key West, this pet-friendly holiday home is conveniently situated just 0.6 miles from Key West International Airport and approximately 6.4 kilometres from the Southernmost Point and Ernest Hemingway Home and Museum.
This 74 square metre, two-bedroom house offers air conditioning, a fully equipped kitchen with a dishwasher, and resort amenities including a heated outdoor swimming pool, hot tub, and fitness centre, ensuring a comfortable stay for you and your dog-friendly companions.
Duval Hideaway | Dog-friendly W/ Shared Hot Tub - Key West, FL
9.8 26 reviews
Key West, FL
14/07 – 16/07
£303/nighttotal: £606 (2 )

Duval Hideaway | Dog-friendly W/ Shared Hot Tub

3 5
apartment, Key West
Ideally situated in Old Town Key West, this apartment is just steps from Duval Street's attractions and a mere 320 meters from Fort Zachary Taylor State Park beach.
This pet-friendly apartment offers a private patio with a grill, shared hot tub, and off-street parking, sleeping up to six guests across three bedrooms with a fully equipped kitchen and washer/dryer.
Conch Keys | Private Pool & Outdoor Bar Paradise! - Key West, FL
Key West, FL
13/12 – 10/01
£388/nighttotal: £10864 (28 )

Conch Keys | Private Pool & Outdoor Bar Paradise!

2 3
apartment, Key West
Situated in Key West's White St. Gallery district, this pet-friendly apartment offers easy access to Duval Street, the Southernmost Point, Ernest Hemingway Home, and Fort Zachary Taylor Historic State Park, with off-street and covered parking a significant advantage.
Boasting a private pool and an entertainment-ready patio with a covered outdoor bar, this renovated 152 square meter apartment features 2 bedrooms and 2 bathrooms, comfortably accommodating up to 4 guests with its coastal-modern aesthetic and fully equipped kitchen.
Charming Island Retreat With Balcony, King Bed, Desk Space & Dog-friendly Vibe - Key West, FL
Key West, FL
01/07 – 31/07
£136/nighttotal: £4080 (30 )

Charming Island Retreat With Balcony, King Bed, Desk Space & Dog-friendly Vibe

1 2
apartment, Key West
Located in Key West's prime Old Town, this apartment is just one block from Duval Street and within easy walking distance of the Ernest Hemingway Home & Museum and the Key West Lighthouse.
This pet-friendly apartment offers a two-level, 70-square-meter space for up to four guests, featuring a fully equipped kitchen, a dedicated workspace, and a semi-private balcony, with your well-behaved dog up to 22.5 kg welcome.

Best Key West, FL holiday rentals with a balcony

Enjoy the comfort of a private balcony during your stay in Key West, FL by choosing from top vacation rental options. Whether you’re looking for a condo vacation rental or a short term vacation rental, these selections provide a relaxing outdoor space.

Spacious Waterfront 4 Bedroom Home - Key West, FL
9.6 93 reviews
Key West, FL
25/09 – 27/09
£1493/nighttotal: £2986 (2 )

Spacious Waterfront 4 Bedroom Home

4 4
apartment, Key West
Boasting a private waterfront pool and located in the exclusive gated Key Cove community on an quiet lane, this Key West apartment offers a secluded yet convenient base, just a short drive from Old Town and within walking distance of grocery stores and the island's largest shopping centre.
This spacious 223 square meter, four-bedroom apartment is perfectly pet-friendly, featuring two luxurious en-suite master bedrooms with King beds and direct balcony access, a gourmet kitchen, and an expansive open-plan living area with stunning water views, ideal for families and groups seeking a dog-friendly seaside escape with ample off-street parking.
The James Suite | Second Floor King - Key West, FL
9.1 44 reviews
Key West, FL
19/07 – 21/07
£291/nighttotal: £582 (2 )

The James Suite | Second Floor King

1 4
apartment, Key West
Located in the Key West Historic District, this pet-friendly apartment is just 160 meters from Duval Street and within easy reach of the Historic Seaport and Mallory Square.
This 26 square meter apartment offers a private room with an en-suite bathroom and balcony, accommodating up to 4 guests with a daybed and twin trundle in the adjoining sitting room, and guests enjoy complimentary access to a swimming pool and the historic Curry Mansion.
Opal Key Resort & Marina - Key West, FL
8.9 10403 reviews
Key West, FL
19/07 – 21/07
£353/nighttotal: £706 (2 )

Opal Key Resort & Marina

1 4
resort, Key West
Ocean Key Resort & Spa, a luxury resort in Key West, boasts a prime waterfront position directly on the Gulf of Mexico, just a 1-minute walk from Mallory Square and the entertainment of Duval Street.
This pet-friendly resort offers guests a relaxing stay with amenities including a swimming pool, spa, and on-site dining, whilst being conveniently located near the beach.
66 M² House ∙ 1 Bedroom ∙ 2 Guests - Key West, FL
10 1 review
Key West, FL
01/07 – 31/08
£104/nighttotal: £6344 (61 )

66 M² House ∙ 1 Bedroom ∙ 2 Guests

1 2
house, Key West
Located in historic Old Town Key West, this pet-friendly house is just a few blocks from Duval Street, offering easy walking access to shops and restaurants.
This dog-friendly one-bedroom house, ideal for two guests, features a kitchenette, a king-size bed, air conditioning, and access to a shared swimming pool within a secure gated community.
Sunnyside Up - Shared Pool - Key West, FL
9.8 10 reviews
Key West, FL
01/06 – 02/06
£560/nightfor 1 night

Sunnyside Up - Shared Pool

2 4
apartment, Key West
This pet-friendly apartment is located in Old Town Key West, just 800 metres from the beach and a 15-minute walk to Duval Street.
Offering 108 square metres of living space with two bedrooms and two bathrooms, this apartment boasts a shared swimming pool and a garden, perfect for families and guests with pets.
The Curry Poolside | Ground Floor Two Queens - Key West, FL
9.4 6 reviews
Key West, FL
01/06 – 02/06
£277/nightfor 1 night

The Curry Poolside | Ground Floor Two Queens

1 4
apartment, Key West
This pet-friendly apartment is situated in the Key West Historic District, just 80 metres from Duval Street and within walking distance of the Historic Seaport and Mallory Square.
Offering a historic mansion experience with a shared heated pool and wrap-around porches, this apartment allows up to 4 guests and is ideal for travellers seeking a dog-friendly getaway near the seaside.
Seaport Serenity Cottage - Quiet And Quaint - Key West, FL
Key West, FL
13/12 – 10/01
£332/nighttotal: £9296 (28 )

Seaport Serenity Cottage - Quiet And Quaint

1 3
house, Key West
Just 0.97 kilometres from the city centre, this Key West cottage is a 17-minute walk from Mallory Square and one kilometre from the Ernest Hemingway Home and Museum.
This pet-friendly house welcomes up to 11 guests and offers a private terrace, complimentary parking, and is a 14-minute walk to Simonton Street Beach, making it ideal for travellers with pets.
Waterfront Dock Pool Downtown Near Duval Pet - Key West, FL
10 7 reviews
Key West, FL
25/09 – 27/09
£747/nighttotal: £1494 (2 )

Waterfront Dock Pool Downtown Near Duval Pet

2 4
apartment, Key West
This pet-friendly apartment in Key West's Meadows neighbourhood is less than 1.6 kilometres from Duval Street, the Historic Seaport, and the Hemingway House.
Enjoy direct waterfront views from your private balcony, with access to a shared heated pool, tiki bar, and boat slip, all within easy reach of Key West International Airport.

Destinations nearby

Best family friendly Key West, FL holiday rentals

Finding family-friendly vacation rentals in Key West, FL ensures everyone enjoys a comfortable and convenient trip. From spacious vacation home rentals to a short term vacation rental, these options are perfect for families seeking memorable stays together.

Poolside Paradise/3bed, 2.5 Bath - Key West, FL
10 18 reviews
Key West, FL
14/07 – 20/07
£873/nighttotal: £5238 (6 )

Poolside Paradise/3bed, 2.5 Bath

1 5
apartment, Key West
Just 80 metres from Duval Street, this two-bedroom apartment offers a prime location in Key West, ideal for exploring the area's attractions with your dog-friendly holiday.
This pet-friendly accommodation boasts a private heated pool and a fully equipped kitchen, providing a comfortable and convenient stay for up to six guests, including your pets.
Cozy Spot Next To Duval With Swim Spa - 2bed/2bath - Key West, FL
10 2 reviews
Key West, FL
01/07 – 31/07
£168/nighttotal: £5040 (30 )

Cozy Spot Next To Duval With Swim Spa - 2bed/2bath

2 2
apartment, Key West
Just 500 meters from Duval Street and a 2-minute walk to the Ernest Hemingway Home and Museum, this apartment offers a prime Old Town Key West location with easy access to dining and shopping.
This two-bedroom, two-bathroom apartment is pet-friendly, featuring a full kitchen, laundry facilities, and a swim spa in a shared outdoor space, ideal for families or couples seeking an extended stay in Key West.
Studio Flat ∙ 2 Guests - Key West, FL
Key West, FL
05/06 – 07/06
£446/nighttotal: £892 (2 )

Studio Flat ∙ 2 Guests

1 2
studio, Key West
Located in the prime downtown district of Key West, this studio apartment offers exceptional walkability to numerous attractions, just 600 meters from Duval Street.
This pet-friendly studio welcomes pets up to 18kg for a nightly fee and features a private back deck, a shared swimming pool, and a fully-equipped kitchen, making it ideal for travellers with pets.
Doubletree By Hilton Grand Key Resort - Key West, FL
8.0 3092 reviews
Key West, FL
30/05 – 06/06
£170/nighttotal: £1190 (7 )

Doubletree By Hilton Grand Key Resort

1 2
resort, Key West
Offering a complimentary shuttle service to historic Old Town Key West and Duval Street, this pet-friendly resort is conveniently located just a 3.2-kilometre drive from Key West International Airport.
This resort boasts a sparkling swimming pool with a poolside tiki bar, a fitness centre, and on-site dining at the Palm Haven Restaurant, ensuring a comfortable stay for you and your dog-friendly companion.
Blue Horizon Hideaway - Key West, FL
Key West, FL
13/12 – 10/01
£228/nighttotal: £6384 (28 )

Blue Horizon Hideaway

3 3
house, Key West
This Key West townhouse offers a serene waterfront retreat, boasting a prime location on two sides within the Key Cove community, just a short distance from the vibrant shopping, dining, and Duval Street.
This dog-friendly accommodation features a private outdoor patio, a shared community pool, and an open-concept first floor with a chef's kitchen, perfect for families and guests with pets, sleeping up to six people.
Aqua Lodges At Hurricane Hole Marina - Key West, FL
Key West, FL
01/06 – 02/06
£500/nightfor 1 night

Aqua Lodges At Hurricane Hole Marina

2 4
island, Stock Island
This houseboat offers a unique waterfront experience on Stock Island, a mere 10-minute drive from Key West's Duval Street and the Key West Tropical Forest and Botanical Garden, and is situated within 7.4 kilometres of Smathers Beach and Mallory Square.
Enjoy on-site activities like paddleboarding and kayaking, with this pet-friendly accommodation also featuring a full kitchen, separate sitting area, and complimentary Wi-Fi, making it ideal for travellers seeking dog-friendly stays near the seaside.
Sunset At The Keys - Key West, FL
9.7 7 reviews
Key West, FL
13/12 – 10/01
£327/nighttotal: £9156 (28 )

Sunset At The Keys

4 3
apartment, Key West
Centrally located in Key West's prime Old Town district, this fully renovated classic duplex offers peaceful island living just 500 meters from parks, the beach, and renowned restaurants.
This pet-friendly apartment boasts modern amenities including air conditioning and a full kitchen, making it ideal for families, couples, and business travellers seeking a convenient and dog-friendly seaside escape.
Apartment ∙ 2 Bedrooms ∙ 9 Guests - Key West, FL
10 2 reviews
Key West, FL
20/07 – 23/07
£737/nighttotal: £2211 (3 )

Apartment ∙ 2 Bedrooms ∙ 9 Guests

2 4
apartment, Key West
Located in a convenient Key West district, this apartment offers easy access to the island's attractions via walking, biking, or scooter rentals, and is a pet-friendly choice for your holiday.
This spacious two-bedroom, two-bathroom apartment boasts a private balcony from each bedroom, a fully equipped galley kitchen, and a tropical backyard oasis with a shared swimming pool and grill, making it ideal for families and guests travelling with their pets.
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