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Key West, FL short term rentals
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Best Short term and Weekly rentals in Key West, FL

Search Family Short-Term Rentals in Key West, FL

Waterfront family vacations in Key West, FL work best with proximity to the beach and plenty of room for everyone to spread out.

La Casa De Luna - 1 Bd/1b Condo Just Off Upper Duval - Key West, FL
9.6 109 reviews
Key West, FL
06/20 – 06/21
$613/nightfor 1 night

La Casa De Luna - 1 Bd/1b Condo Just Off Upper Duval

2 2
apartment , Key West
This Old Town Key West condo is located steps from the City Zoo Gallery and Duval Street, within a 10-minute drive of the Ernest Hemingway Home and Museum and Florida Keys beaches.
This 450-square-foot apartment features one bedroom, one bathroom, accommodates four guests, and includes a private pool, balcony, fully equipped kitchen, in-unit laundry, and free internet access.
Two Fully Independent Units In A Duplex, With Independent Entrances. One Rent! - Key West, FL
8.0 1 review
Key West, FL
12/21 – 01/18
$510/nighttotal: $14280 (28 )

Two Fully Independent Units In A Duplex, With Independent Entrances. One Rent!

4 1
apartment , Key West
This Key West duplex, located in the Historic District, offers easy walking access to the Historic Seaport, Duval Street, and beaches.
This four-bedroom, four-bathroom rental sleeps twelve, features two fully renovated homes, a fully equipped kitchen with dishwasher, and includes parking; a minimum 28-night stay is required.
Coastal Comfort & 3/4 Time Compound - Key West, FL
9.6 5 reviews
Key West, FL
09/02 – 09/05
$2490/nighttotal: $7470 (3 )

Coastal Comfort & 3/4 Time Compound

8 2
apartment , Key West
This expansive 4000 sq ft estate in Key West's Key Cove Landings offers a quiet neighborhood setting within walking distance of Publix and the island's largest shopping center, and is a short drive to landmarks like the Ernest Hemingway Home and Museum, Southernmost Point, and Fort Zachary Taylor Historic State Park.
This luxury compound accommodates up to 16 guests with 8 bedrooms, featuring 7 bathrooms, a chef's kitchen with gourmet appliances, a private heated pool with a BBQ grill, high-speed internet, and central air conditioning.
Panoramic 3br/3ba Condo - Direct Beach Ocean Front - Key West, FL
10 129 reviews
Key West, FL
10/17 – 10/24
$1116/nighttotal: $7812 (7 )

Panoramic 3br/3ba Condo - Direct Beach Ocean Front

3 2
apartment , Key West
This 3-bedroom Key West condo is located in Midtown, just 2 miles from both the airport and Mallory Square, placing you within easy reach of the island's best attractions. Guests rave about the excellent location and amenities, making this a popular choice for travelers. This spacious apartment offers 2200 square feet of living space, comfortably accommodating up to 8 guests. Enjoy a range of amenities including a private pool, jacuzzi, sauna, and a terrace with stunning ocean views.

Best Key West, FL lodging with a balcony

Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 311 reviews
Key West, FL
07/24 – 07/28
$1156/nighttotal: $4624 (4 )

Waterfront Dock Pool Condo Near Duval St Pet Ok

2 7
apartment , Key West
This waterfront Key West condo, located in historic Downtown Key West, is one mile from Duval Street, the Historic Seaport, and the Hemingway House.
The 1350-square-foot unit features two bedrooms, two bathrooms, a pull-out couch accommodating six guests, a private balcony overlooking the harbor and pool, and a reserved boat slip (up to 40 feet, 13-foot beam) with power, water, and a covered fish-cleaning station.
A Key Escape ~ 3 Bedroom, 2.5 Bathroom Home In Old Town /Private Heated Pool! - Key West, FL
9.8 108 reviews
Key West, FL
07/24 – 07/28
$1266/nighttotal: $5064 (4 )

A Key Escape ~ 3 Bedroom, 2.5 Bathroom Home In Old Town /Private Heated Pool!

3 7
apartment , Key West
This Key West townhome, located in the Historic District, is blocks from Duval Street and near the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The 1,570-square-foot property features three bedrooms, three bathrooms, and accommodates eight guests, offering a private pool, gas grill, and concierge service for arranging activities and pre-arrival grocery stocking.
**Mayas Secret Treasure @ Duval** Pool & Balcony Over Duval + Last Key Services - Key West, FL
9.9 115 reviews
Key West, FL
07/24 – 07/28
$2327/nighttotal: $9308 (4 )

**Mayas Secret Treasure @ Duval** Pool & Balcony Over Duval + Last Key Services

3 7
apartment , Key West
This Old Town Key West condo is a five-minute walk from Duval Street and the Ernest Hemingway Home and Museum, offering easy access to beaches like South Beach within a 15-minute drive.
This 2,510-square-foot three-bedroom, three-bathroom rental sleeps six and boasts a private pool, a fully equipped kitchen, free Wi-Fi, and access to a rooftop terrace with grills; nearby attractions include the Florida Keys Beaches.
The Curry Poolside | Ground  Floor King - Key West, FL
10 2 reviews
Key West, FL
06/20 – 06/21
$431/nightfor 1 night

The Curry Poolside | Ground Floor King

1 2
apartment , Key West
This Key West Historic District rental is steps from the Curry Mansion Museum and Duval Street, placing you within a 10-minute drive of Mallory Square and Florida Keys beaches.
The one-bedroom, one-bathroom apartment sleeps two guests and includes in-unit laundry, a private balcony, and access to a swimming pool, garden, and concierge services.

Frequently Asked Questions about short term rentals in Key West, FL

  • Which top landmarks you shouldn't miss in Key West, FL?

    You can't miss the Southernmost Point Buoy, the iconic marker at the bottom of the continental US. The Hemingway House is a must-see, especially if you're a fan of the author. And of course, you have to stroll down Duval Street with its shops and restaurants.
  • What are the best short term rentals in Key West, FL?

  • What types of short-term rentals are available in Key West?

    If you are looking for accommodations in Key West you can look for short-term rentals which would allow you to get the best experiences. These short-term rentals can offer you more comfort and privacy than hotels. Hence, many families visiting Key West prefer to choose them over hotels. Short-term rentals allow you to stay longer and get all the facilities and amenities you need with your family. Also, you can find many pet-friendly short-term rentals which would allow you to bring your pet along. These apartments and condos come with various modern kitchen and bathroom facilities and amenities offering you excellent holiday experiences.
  • What kind of weather can travelers expect in Key West, FL?

    Key West has a tropical climate, so expect sunshine and warm temperatures year-round. You'll see the most rain during the summer months, but even then, it's usually just a quick shower. Don't forget to pack sunscreen and a hat!
  • What are the best short term rentals with a pool in Key West, FL?

  • What are the best kid-friendly attractions in Key West?

    1. Shipwreck Treasure Museum - When you are with the kids you can visit the Shipwreck Treasure Museum where kids can hold and explore once-lost treasures and various shipwreck artefacts.
    2. Mallory Square - If you are with the kids you can head to Mallory Square where kids can enjoy food and drinks and even get the best entertainment on the streets and in live theatres.
    3. Fort Zachary Taylor State Park - Kids would love to explore the Fort Zachary Taylor State Park where they can swim and lounge and make the most of their time on the island.
  • What are the most popular festivals and events in Key West, FL?

    Key West is known for its lively events, like Fantasy Fest in October, a colorful celebration with parades and costumes. The Key West Songwriters Festival in May is a great time to catch live music. And don't forget the annual Hemingway Days in July, celebrating the famous author.
  • What are the best short term rentals with a jacuzzi in Key West, FL?

    The best short term rentals with a jacuzzi in Key West, FL are Secret Courtyard Cottage, Southernmost Sanctuary and Sunrise Suites Panama Suite #310.

  • What's the best neighbourhood to stay close to the city centre?

    If you are planning to stay in Key West you can look for White Street Gallery District which is close to the city centre and Old Town. This is one of the best locations on the island which allows you to move in any direction. Hence, you can look for rental apartments and even hotels which you can find here based on your requirements and budget. This also allows you to be close to many of the locations like Fort Zachary Taylor Historic State Park. This neighbourhood sits right between the Old Town and New Town making it convenient for you to explore either side of the island.
  • Are there any famous stadiums or sports arenas in Key West, FL?

    Key West doesn't have any major stadiums or sports arenas. It's more of a laid-back island vibe, focused on beaches and water activities.
  • What are the best short term rentals for families and kids in Key West, FL?

  • What are the best shopping malls in Key West?

    1. Searstown Shopping Center - If you have shopping on your mind you can head to Searstown Shopping Center where you can find plenty of local shops and boutiques where you can shop conveniently.
    2. Overseas Market - When you intend to shop for local products and groceries and much more you can head to Overseas Market where you can find various local stores and departmental shops on the island. . Duval Square Mall - While it might not be a huge mall as you would expect Duval Square Mall can offer you a good shopping experience when you are shopping in Key West.
  • What notable natural landmarks are near Key West, FL?

    Just a short boat ride from Key West, you'll find the beautiful Dry Tortugas National Park, home to Fort Jefferson, a massive 19th-century fort. The park is also a great place to snorkel or dive among colorful coral reefs.
  • What is the best place to book a short-term rental for the Key Lime Festival in Key West?

    If you are visiting Key West for the Key Lime Festival on the island you should look for short-term rentals in White Street Gallery District. Being close to the Old Town, this is one of the best neighbourhoods that offer a strategic position to explore more on the island. You can find plenty of rental apartments and condos here that allow you to stay like a local. Also, you can be close to many local attractions which allows you to save time and ensure that you can cover more restaurants, bars, breweries, museums and entertainment venues.
  • What part of Key West, FL is ideal for finding lodging?

    Old Town is a great area for lodging, with lots of historic buildings and charming guesthouses. You'll be close to Duval Street and all the action. If you prefer a quieter stay, you can find more secluded options on the quieter side of the island, like the Sunset Key area.

Destinations nearby

Best Key West, FL lodging with a kitchen

Colony Sunset- Bright And Airy Cottage - Key West, FL
9.7 25 reviews
Key West, FL
07/02 – 07/07
$447/nighttotal: $2235 (5 )

Colony Sunset- Bright And Airy Cottage

1 2
apartment , Key West
The Colony Sunset Suite is a one-bedroom cottage located in Old Town Key West, just a short walk from Duval Street and a quick bike ride to beaches, shops, and restaurants. This cottage has received excellent ratings for location, cleanliness, and overall experience from previous guests.
This charming cottage features a spacious layout, accommodating up to 4 guests, and offers a private deck, shared pool access, and a fully equipped kitchen. Guests can enjoy a comfortable king-size bed, a flat-screen TV, and nautical-themed décor while relaxing in this peaceful retreat.
Antigua Retreat- 2br 2ba Waterfront Condo W/ Pool & Boat Slip - Key West, FL
9.4 150 reviews
Key West, FL
07/02 – 07/07
$607/nighttotal: $3035 (5 )

Antigua Retreat- 2br 2ba Waterfront Condo W/ Pool & Boat Slip

2 2
apartment , Key West
This waterfront condo is located in the Meadows district of Key West, just one mile from the Duval Street area and a short bike ride to Old Town, offering a peaceful retreat while remaining close to the action. This highly-rated apartment consistently receives excellent reviews from guests.
This two-bedroom, two-bathroom home can comfortably accommodate up to six guests. Enjoy a private balcony overlooking the water, a heated pool, and a grill, making this an excellent choice for families and groups looking for a comfortable and convenient stay.
Meadows Manor | Elegant Oasis With Private Pool - Key West, FL
8.0 2 reviews
Key West, FL
06/27 – 06/28
$2610/nightfor 1 night

Meadows Manor | Elegant Oasis With Private Pool

4 7
apartment , Key West
This Key West condo offers 4 bedrooms and 4 bathrooms, accommodating up to eight guests, with a private pool and on-site parking, situated centrally for easy access to shops, restaurants, and nightlife, and is a leisurely stroll to the beaches. Enjoy a fully equipped kitchen, in-unit washer and dryer, and exterior security cameras, with contactless check-in for a streamlined arrival experience.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews
Key West, FL
07/25 – 07/27
$607/nighttotal: $1214 (2 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 3
apartment , Key West
This two-bedroom, two-bathroom Key West condo is conveniently located near Key West International Airport, offering easy access to the island's attractions.
Sleeping up to six guests, this second-floor unit features a king and queen bedroom, a queen-size pull-out sofa, a private balcony, in-unit laundry, a fully equipped kitchen with dishwasher, and one designated parking space under the building, plus additional first-come, first-served parking.

Neighborhoods and points of interest in Key West, FL

Best Key West, FL lodging with laundry available

Beachfront Condo, Ocean Views Lg Pools, Pets Ok - Key West, FL
10 2 reviews
Key West, FL
12/21 – 01/18
$330/nighttotal: $9240 (28 )

Beachfront Condo, Ocean Views Lg Pools, Pets Ok

1 1
apartment , Key West
This beachfront Key West condo, minutes from downtown, offers direct Atlantic Ocean views and access.
The one-bedroom, one-bathroom unit sleeps two, includes a kitchen, pool access, parking, and beach chairs, plus a New-to-Market discount for December 24th.
Beach Paradise In The Keys! Location! Location! 2 Blocks To Duval St - Key West, FL
9.4 51 reviews
Key West, FL
06/27 – 06/28
$1297/nightfor 1 night

Beach Paradise In The Keys! Location! Location! 2 Blocks To Duval St

2 7
apartment , Key West
This newly renovated Key West townhome in Truman Annex is two blocks from Duval Street and the beach, near Fort Zachary Taylor Historic State Park, offering prime access to Old Town attractions.
This 1,000-square-foot property boasts three bedrooms, three bathrooms, sleeps eight guests, and features a private courtyard, heated pool access, and amenities including free Wi-Fi and three TVs.
Rum Cay At Sunrise Suites - Key West, FL
9.8 40 reviews
Key West, FL
12/30 – 01/10
$624/nighttotal: $6864 (11 )

Rum Cay At Sunrise Suites

2 5
apartment , Key West
This Rum Cay condo, a 10-minute drive from Duval Street and Key West's attractions, offers a quiet escape near a nature preserve.
The two-bedroom, two-bathroom apartment sleeps six, features a modern kitchen with stainless steel appliances, a private balcony with estuary views, and community pool access.
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
Key West, FL
07/24 – 07/28
$1037/nighttotal: $4148 (4 )

Apartment ∙ 2 Bedrooms ∙ 8 Guests

2 7
apartment , Key West
This downtown Key West condo provides easy walking access to Duval Street and its attractions.
Sleeping up to 10 guests, this two-bedroom, one-bathroom unit features a king bed, two additional king beds in a loft, two pull-out couches, a full kitchen with stove, refrigerator, and Keurig, a balcony overlooking Duval Street, central AC, smart TVs, Wi-Fi, a washer/dryer, and nearby parking.
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