Find short term rentals in Florida Keys at the best prices

11096 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Florida Keys short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Florida Keys

Best family friendly Florida Keys Short term rentals

Among the 11096 accommodations in Florida Keys, here are the 4 best family friendly rentals

Sombrero Beach Tropical Getaway - Florida Keys
9.7 254 reviews

Sombrero Beach Tropical Getaway

apartment, Marathon
This canal-front flat is situated in Marathon, Florida, just a short walk from supermarkets and within 1.6 kilometres of Sombrero Beach. The property has received excellent ratings for cleanliness, location and user experience.
The apartment sleeps four guests and has one bedroom and one bathroom. Amenities include a swimming pool, garden, fitness centre, parking, air conditioning, a kitchen with a fridge and microwave, and free internet access. Guests can enjoy access to a private balcony, a boat ramp, and four bicycles, as well as the option of renting a pontoon or kayak.
Apartment ∙ 5 Bedrooms ∙ 16 Guests - Florida Keys
No reviews

Apartment ∙ 5 Bedrooms ∙ 16 Guests

apartment, Key West
This spacious Key West property is centrally located in downtown, within easy walking distance of many attractions.
The three-unit compound, sleeping up to 16 guests in five bedrooms and four bathrooms, boasts fully equipped kitchens, private outdoor spaces including a hot tub and BBQ, and two on-site washer/dryers.
Apartment ∙ 3 Bedrooms ∙ 10 Guests - Florida Keys
No reviews

Apartment ∙ 3 Bedrooms ∙ 10 Guests

apartment, Key West
The Mesa House, a Key West dwelling in Old Town, is conveniently located near Simonton Street, offering easy access to numerous attractions.
This self-catering property comprises two separate condos, sleeping up to ten guests, and boasts two full kitchens, four cable TVs, free WiFi, a private washer/dryer, and a terrace/balcony plus garden.
Ocean Views At Sangria Sunrise 10% Off Charters - Florida Keys
9.9 193 reviews

Ocean Views At Sangria Sunrise 10% Off Charters

apartment, Tavernier
This Tavernier apartment is directly on the beach, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square metres, suitable for up to four guests. Amenities include a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, a garden, and parking.

Best Florida Keys lodging with a balcony

Modern And Coastal Ocean Pointe 2307 - Florida Keys
10 134 reviews

Modern And Coastal Ocean Pointe 2307

apartment, Tavernier
This oceanfront apartment is located in Tavernier, Florida Keys, approximately 97 kilometres from Miami International Airport and 145 kilometres from Fort Lauderdale International Airport, offering a tranquil escape in a stunning natural setting. The property has received excellent guest reviews and is highly recommended for a relaxing holiday.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a range of amenities including a swimming pool, a jacuzzi, a terrace, a garden, and parking, as well as a fully equipped kitchen and air conditioning, ensuring a comfortable and enjoyable stay.
Beachside Unit 39 Tiki Huts,  Private Beach & Pool - Florida Keys
9.8 190 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

apartment, Key Colony Beach
This apartment is situated in Key Colony Beach, just 3 kilometres from Sunset Park Beach and Coco Plum Beach, and within a 3-kilometre radius of Curry Hammock State Park and San Pablo Catholic Church. It boasts excellent ratings for location, cleanliness, and user experience.
The property has one bedroom and one bathroom, covering 43 square meters and comfortably accommodating up to 4 guests. It includes a fully equipped kitchen, a balcony, and access to a swimming pool, barbecue grills, and a garden, making it ideal for a relaxing and enjoyable stay.
Serene Cozy Cottage In Islamorada With Heated Pool - Florida Keys
9.6 161 reviews

Serene Cozy Cottage In Islamorada With Heated Pool

apartment, Islamorada, Village of Islands
This charming cottage is situated in Islamorada at mile marker 76.7, just a short drive from Caloosa Cove Marina at mile marker 73.5 and Robbie's Marina, offering a peaceful retreat in the Shady Palms community. The cottage boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property features two bedrooms, making it ideal for families or groups of up to four. Guests can enjoy amenities such as a communal heated pool, a fully equipped kitchen, a private garden, a spa, and a starter pack with essential supplies.
Apartment ∙ 4 Bedrooms ∙ 12 Guests - Florida Keys
No reviews

Apartment ∙ 4 Bedrooms ∙ 12 Guests

apartment, Key West
This Key West property, ideally situated in the downtown area, is within easy walking distance of many attractions.
Two separate houses, each with a gourmet kitchen and private washer/dryer, offer six bedrooms sleeping up to twelve guests, a heated pool, and two off-street parking spaces.

Frequently Asked Questions about short term rentals in Florida Keys

  • What attractions should you visit during a week-long stay in the Florida Keys?

    A week in the Florida Keys allows for a taste of its diverse offerings. Start in Key Largo, exploring John Pennekamp Coral Reef State Park for snorkeling or diving. Head down to Islamorada, known as the "Sport Fishing Capital of the World," and consider a fishing charter. Key West is a must-see, with the Ernest Hemingway Home and Museum, Mallory Square for sunset celebrations, and the iconic Southernmost Point Buoy. Don't miss the Seven Mile Bridge, offering stunning views. Consider a day trip to Bahia Honda State Park for beautiful beaches and snorkeling.
  • What are the best short term rentals in Florida Keys?

    Among the short term rentals in Florida Keys, Secret Courtyard Cottage, At Mine | Lovely Suite Steps From Duval Street and Spacious - Private 1 Bed/1 Bath Apt In Everglades are the most popular ones.

  • What attractions should you visit when you spend a month in the Florida Keys?

    A month gives you time for in-depth exploration. Besides the highlights mentioned above, explore the backcountry by kayak or paddleboard in Everglades National Park's Florida Bay section. Visit the History of Diving Museum in Islamorada. Take a day trip to Dry Tortugas National Park by boat or seaplane for snorkeling and exploring Fort Jefferson. Spend time exploring the smaller keys, like Marathon and Big Pine Key, discovering their unique local businesses and relaxed atmosphere. Consider visiting the Turtle Hospital in Marathon. Enjoy the many beaches and water activities each key offers.
  • What are the best short term rentals with a pool in Florida Keys?

  • Can visitors to the Florida Keys witness any unique natural cycles, like cherry blossom season or autumn colors?

    The Florida Keys don't experience the dramatic autumn foliage changes of the northern US or the cherry blossoms of Japan. However, you can witness vibrant coral reefs teeming with life, especially if you snorkel or dive, and enjoy the subtler seasonal changes in marine life and bird migrations.
  • What are the best short term rentals with a jacuzzi in Florida Keys?

    The best short term rentals with a jacuzzi in Florida Keys are Secret Courtyard Cottage, Marco Beach Ocean Suites and Coco Plum Beach & Tennis Club & Marina.

  • What are the most meaningful ways to engage with locals and discover the culture in the Florida Keys?

    To connect with the local culture, visit local restaurants and bars away from the main tourist areas. Many Keys residents are involved in fishing and boating, so attending local events or festivals associated with these activities offers a glimpse into their lives. Exploring the smaller, less-visited keys will provide opportunities to interact with residents in a more relaxed setting. Check local event listings for community events and farmers' markets.
  • What are the best short term rentals for families and kids in Florida Keys?

  • Are there any distinctive cultural activities or hands-on workshops in the Florida Keys?

    The Florida Keys offer various cultural experiences. You can find conch shell crafting workshops and learn about the history and significance of the conch shell to the Keys' culture. Several art galleries showcase local artists' work, reflecting the Keys' unique style and inspiration from the natural environment. Fishing charters and boat tours are also a way to learn about local maritime traditions.
  • What are some secret spots or hidden treasures to visit in the Florida Keys?

    Some lesser-known gems include the less-crowded beaches on the smaller keys like Big Pine Key or Bahia Honda State Park. Explore the mangrove tunnels by kayak or paddleboard in the backcountry. Discover the local artist studios and galleries tucked away in quieter neighborhoods. The nature trails in various state parks offer opportunities to experience the natural beauty away from the main tourist attractions.
  • What should not be left out of your suitcase if you are going to the Florida Keys?

    Pack light clothing, swimwear, sunscreen (high SPF!), sunglasses, a hat, and comfortable walking shoes. Don't forget reef-safe sunscreen to protect the delicate coral reefs. Bring insect repellent, especially if exploring the backcountry. If planning water activities, include appropriate gear like snorkeling equipment or water shoes.
  • What are the most popular festivals in the Florida Keys?

    The Florida Keys host many events throughout the year. Key West's Fantasy Fest is a well-known, adult-oriented Halloween celebration. The annual Conch Republic Independence Celebration in Key West is a quirky and fun event. Many smaller keys also host festivals related to fishing, boating and local culture throughout the year. Check local event calendars for specific dates and details.
  • Where should you try the best local food in the Florida Keys?

    For authentic Keys cuisine, look for restaurants specializing in fresh seafood. Many restaurants offer conch fritters, a local favorite. Explore smaller, family-owned restaurants on the various keys, as they often offer more unique and flavorful dishes reflecting local traditions. Key West and Islamorada have a wide variety of dining options, ranging from casual eateries to upscale restaurants.

Nearby regions

Best Florida Keys lodging with a kitchen

Bay Harbor Lodge - Florida Keys
9.4 1004 reviews

Bay Harbor Lodge

house, Key Largo
The Bay Harbor Lodge is located in Key Largo, a short drive from both Everglades National Park and Pennekamp Coral Reef State Park, offering easy access to two of the area's most popular attractions. It boasts excellent user, location and cleanliness ratings, making it a great choice for travellers.
The lodge provides a comfortable and convenient stay with a range of amenities, including a seasonal outdoor pool, a small library and concierge services. Guests can enjoy the small beach and fishing pier, as well as free Wi-Fi access in public areas.
Bird Of Paradise: 3br Condo, Atlantic Views, Beach - Florida Keys
9.3 66 reviews

Bird Of Paradise: 3br Condo, Atlantic Views, Beach

apartment, Marathon
This apartment is located in Marathon, just a short walk from Curry Hammock State Park and Coco Plum Beach, and within a 3-mile radius of Sunset Park Beach and Captain Hooks Marina and Dive Center. It has received excellent ratings for location, cleanliness, and user experience.
The apartment has three bedrooms, two bathrooms, and can comfortably accommodate six guests. It features a private pool, a garden, a terrace, a fitness centre, a tennis court, parking, a fully equipped kitchen, and a host of other amenities for a relaxing and enjoyable stay.
Full Time Lic Mgr - Modern 2/2 Coconut Palm Villa - Oceanfront Beach Resort! - Florida Keys
9.4 67 reviews

Full Time Lic Mgr - Modern 2/2 Coconut Palm Villa - Oceanfront Beach Resort!

apartment, Key Largo
This smoke-free villa is located near the sea in Key Largo, within 1.6km of Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, and within 4.8km of Jacob's Aquatic Center and Bluefin Rock Harbor Marina. The property enjoys an excellent rating, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The "Licensed Manager - Modern 2/2 Coconut Palm Villa - Oceanfront Beach Resort!" accommodation spans 102 square metres and can comfortably accommodate up to 6 guests. The villa offers a range of amenities and activities, including a water park, outdoor pool, garden, tennis court, BBQ facilities, and a fully equipped kitchen.
Toes In The Sand - 2 Bedroom Condo Sleeps 4 - Florida Keys
9.6 664 reviews

Toes In The Sand - 2 Bedroom Condo Sleeps 4

apartment, Tavernier
This apartment is situated in Ocean Pointe Suites, located between Key Largo and Islamorada, just a short distance from Tavernier's main attractions. The property has received excellent ratings for its location, cleanliness and overall experience.
The apartment is perfect for families, with a pull-out sofa bed and convertible chair for comfortable sleeping arrangements. Guests can enjoy a range of amenities, including a heated pool, hot tub, tennis courts, pickleball courts, a playground, BBQ areas, a marina with boat slip rentals, a full kitchen, laundry facilities, free high-speed WiFi and a cooler.

Best Florida Keys lodging with laundry available

Cottage With Swimming Pool And Dockage, Just Minutes To Key West! - Florida Keys
9.0 173 reviews

Cottage With Swimming Pool And Dockage, Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key oceanfront cottage offers stunning views and direct beach access, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
The 36-square-metre self-catering property sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, private terrace, swimming pool, and free Wi-Fi.
Boot Key Harbor Retreat | Pool & Breakfast - Florida Keys
10 18 reviews

Boot Key Harbor Retreat | Pool & Breakfast

apartment, Marathon
This luxury waterfront suite in Marathon is located on Boot Key Harbor, offering direct access to boat slips and situated midway between Islamorada and Key West.
This one-bedroom, one-bathroom apartment accommodates up to four guests and features a gourmet kitchen, spa-inspired bathroom, and access to resort amenities including a swimming pool, fitness centre, and complimentary daily breakfast, with bicycles, kayaks, and paddleboards available for hire.
Cozyhome Near National Parks Between Miami & Keys - Florida Keys
9.9 204 reviews

Cozyhome Near National Parks Between Miami & Keys

apartment, Homestead
This Homestead property is conveniently located within walking distance of several parks, including Losner Park and J.D. Redd Park, and close to the Pioneer Florida Museum and Village. The property has excellent user, location, and cleanliness ratings.
The three-bedroom house can accommodate up to eight guests and features a fully equipped kitchen, two bathrooms, and a dining area. Amenities include air conditioning, a garden, barbecue grills, a washer and dryer, and free Wi-Fi, making it ideal for families or groups seeking a comfortable and convenient stay.
Kawama Lake View Unit L-2 - Florida Keys
9.5 53 reviews

Kawama Lake View Unit L-2

apartment, Key Largo
This townhome is situated in the Kawama Yacht Club gated community at mile marker 100 in Key Largo, just a short walk from Dolphin Plus and popular restaurants like Backyard Key Largo Fisheries and Pilot House. This property boasts excellent user, location and cleanliness ratings.
This spacious three-bedroom, three-bathroom property can accommodate up to eight guests. The townhome offers a range of amenities including two heated swimming pools, a playground, BBQ areas, pickleball/tennis courts, and multiple balconies with lagoon views.
©2026 cozycozy.com