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Florida Keys short term rentals
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Best Short term and Weekly rentals in Florida Keys

Best family friendly Florida Keys Short term rentals

Among the 8594 accommodations in Florida Keys, here are the 4 best family friendly rentals

Apartment ∙ 6 Bedrooms ∙ 14 Guests - Florida Keys
Florida Keys
24/07 – 27/07
$4179/nighttotal: $12537 (3 )

Apartment ∙ 6 Bedrooms ∙ 14 Guests

6 14
apartment , Key West
This luxurious six-bedroom Key West property, situated in the Modern Keys gated community, offers easy access to Key Haven and Stock Island boat ramps.
Sleeping up to 14 guests, the spacious house boasts a fully equipped kitchen, six bathrooms (five en-suite), a private terrace, garden, parking for four vehicles plus a boat trailer, and high-speed internet; private boat excursions and chauffeur services are available.
Waterfront Bungalow W/ Full Kitchen, Pool Access & Close To Key West Beaches - Florida Keys
Florida Keys
22/08 – 23/08
$739/nightfor 1 night

Waterfront Bungalow W/ Full Kitchen, Pool Access & Close To Key West Beaches

3 2
apartment , Big Pine Key
This Summerland Key flat offers direct access to Looe Key Reef, a prime spot for diving, and is a short drive from Bahia Honda State Park, providing a rural setting with beach access for water sports enthusiasts.
This 61.3 square meter apartment accommodates up to six guests and includes a kitchen with essential appliances, complimentary kayaks, paddleboards, and bicycles, plus a shared outdoor pool open year-round, with pets permitted for an extra fee.
Open Water Views |  32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape - Florida Keys
9.0 2 reviews
Florida Keys
22/08 – 23/08
$1174/nightfor 1 night

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

2 2
apartment , Cudjoe Key
This waterfront holiday flat in the Venture Out community on Cudjoe Key offers direct open water views and convenient access to restaurants such as Square Grouper and Kiki's Sandbar, located within a 10-minute drive, with Key West being a 20-minute drive away.
This 80-square-metre holiday flat accommodates up to six guests across two bedrooms and features a fully equipped kitchen with stainless steel appliances, air conditioning, Wi-Fi, a swimming pool, jacuzzi, and a 35-foot seawall suitable for boats up to 32 feet, complete with a private fish-cleaning station.
Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated! - Florida Keys
9.8 55 reviews
Florida Keys
19/06 – 23/06
$422/nighttotal: $1688 (4 )

Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated!

1 4
cottage , Cudjoe Key
Palm Cottage, a two-bedroom holiday home in Summerland Key, is situated within 2km of Florida Keys Beaches, Crab Key, and Pye Key, offering easy access to these attractions and the Coupon Bight Aquatic Preserve within 10km.
This 45-square-metre self-catering property sleeps four guests and boasts a private patio, swimming pool, garden, and fully equipped kitchen including a washing machine; free Wi-Fi is also provided.

Best Florida Keys lodging with a balcony

Walk To Beach: Florida Keys Gem W/ Ocean Views - Florida Keys
9.6 4 reviews
Florida Keys
25/11 – 27/11
$1092/nighttotal: $2184 (2 )

Walk To Beach: Florida Keys Gem W/ Ocean Views

2 6
apartment , Layton
This Layton, Long Key beachfront townhouse boasts direct beach access with provided chairs and umbrellas, situated 3.2km from Long Key State Park and 11.3km from the Dolphin Research Centre.
This 127 square metre property sleeps up to six guests in two bedrooms and two bathrooms, and offers three balconies with ocean views, a well-equipped kitchen, a swimming pool, free Wi-Fi, and parking, plus access to community amenities including a boat dock and picnic area.
Coco Plum Beach & Tennis Club & Marina - Florida Keys
9.2 769 reviews
Florida Keys
20/06 – 27/06
$479/nighttotal: $3353 (7 )

Coco Plum Beach & Tennis Club & Marina

2 5
aparthotel , Marathon
Coco Plum Beach & Tennis Club & Marina is a 2-star aparthotel in Marathon, Florida, situated just 1.4 miles from the Florida Keys Aquarium Encounters. The property has received excellent user ratings for its cleanliness, location and overall experience.
These spacious apartments can comfortably accommodate up to six guests and feature a living room, dining room, and a fully equipped kitchen. Coco Plum Beach & Tennis Club & Marina offers a range of amenities, including a swimming pool, tennis court, hot tub, garden, and a bar, ensuring a relaxing and enjoyable stay.
Signature 1br Ocean View Suite W/ Beach Access - Florida Keys
Florida Keys
22/08 – 23/08
$494/nightfor 1 night

Signature 1br Ocean View Suite W/ Beach Access

1 2
aparthotel , Tavernier
This aparthotel in Tavernier offers direct Atlantic Ocean access and sweeping ocean views, situated within 17 kilometres of John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park.
Each one-bedroom suite at this aparthotel features a fully equipped gourmet kitchen, a private oceanfront balcony, and in-unit laundry, with on-site amenities including a private beach, Junior Olympic swimming pool, Jacuzzi hot tub, marina, and tennis courts, accommodating up to four guests.
Beachside Unit 12 - Key Colony - Florida Keys
9.8 156 reviews
Florida Keys
09/07 – 13/07
$437/nighttotal: $1748 (4 )

Beachside Unit 12 - Key Colony

1 4
apartment , Key Colony Beach
This apartment is situated in Key Colony Beach, just a short walk from Sunset Park Beach and Coco Plum Beach, and within 3km of Curry Hammock State Park and San Pablo Catholic Church. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The flat is 43 square metres and can accommodate up to four guests. You'll find a well-equipped kitchen, a balcony, and access to a swimming pool, barbecue grills, and a garden.

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

Couples' Retreat 1br W/ Pool & Ocean View - Florida Keys
Florida Keys
22/08 – 23/08
$437/nightfor 1 night

Couples' Retreat 1br W/ Pool & Ocean View

1 2
apartment , Tavernier
This oceanfront resort condominium in Tavernier, Florida, is located 1.2 kilometres from the History of Diving Museum and 1.5 kilometres from John Pennekamp Coral Reef State Park.
This 56 square metre apartment accommodates up to four guests and features two bedrooms, one bathroom, air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, and access to a communal swimming pool, hot tub, and tennis courts.
Seas The Day  3bed/2.5bath Modern Townhome With Swim Spa In Marathon - Florida Keys
9.4 28 reviews
Florida Keys
20/06 – 27/06
$520/nighttotal: $3640 (7 )

Seas The Day 3bed/2.5bath Modern Townhome With Swim Spa In Marathon

3 5
apartment , Marathon
This Marathon holiday home is situated 1.8km from Crane Point Museum and within 5km of the Marathon Air Museum and Florida Keys Country Club.
Sleeping eight guests, this three-bedroom property boasts a fully equipped kitchen, private balcony, barbecue grills, free Wi-Fi, a spa, and parking; all within easy reach of Captain Hooks Marina and Dive Centre and Fishermen's Community Hospital.
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |Bbq - Florida Keys
10 167 reviews
Florida Keys
25/11 – 27/11
$596/nighttotal: $1192 (2 )

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |Bbq

2 6
apartment , Tavernier
This oceanfront apartment is situated in Tavernier, Florida Keys, at mile marker 92, offering easy access to the Tavernier Creek for both bay and ocean activities. It has received excellent user ratings, indicating a comfortable and enjoyable stay for guests.
The apartment spans 78 square metres and comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities within the gated resort community, including a heated pool, jacuzzi, BBQ picnic area, tennis courts, a private beach, a dock and marina, a boat ramp, boat and trailer parking, and a waterfront café.
2bd/1ba Waterfront Retreat W/35’ Dock - Florida Keys
9.6 24 reviews
Florida Keys
22/08 – 23/08
$519/nightfor 1 night

2bd/1ba Waterfront Retreat W/35’ Dock

1 2
apartment , Cudjoe Key
This Cudjoe Key waterfront holiday home is situated within the Venture Out community, offering easy access to restaurants such as the Square Grouper and the Niles Road Nature Trail.
Sleeping up to five guests, this two-bedroom, one-bathroom property boasts a private pool and jacuzzi, direct ocean access, and is close to Murray's Market for grocery shopping.

Best Florida Keys lodging with laundry available

P29  - Charming 3 Bedroom 2 Bath Duplex With Deep Water Dockage And Cabana Club Membership - Florida Keys
9.7 43 reviews
Florida Keys
20/06 – 27/06
$479/nighttotal: $3353 (7 )

P29 - Charming 3 Bedroom 2 Bath Duplex With Deep Water Dockage And Cabana Club Membership

3 1
apartment , Key Colony Beach
This three-bedroom apartment is conveniently located in Key Colony Beach, just a short distance from the Marathon airport and within walking distance of the beach. It has received excellent ratings for user experience, location, and cleanliness.
This spacious property is perfect for families or groups of up to six people, offering a comfortable and relaxing stay. Guests can enjoy a private hot tub, a deep-water dock, access to the Key Colony Beach Cabana Club, and a range of other amenities including a fully equipped kitchen, a garden, and a swimming pool.
Cozy Studio In West Kendall - Florida Keys
9.5 17 reviews
Florida Keys
31/07 – 03/08
$212/nighttotal: $636 (3 )

Cozy Studio In West Kendall

1 2
apartment , Country Walk
This studio flat is located in Country Walk, a short walk from Publix and Walgreens.
The self-catering apartment comes equipped with a fridge, freezer, microwave oven, washer and dryer, and can accommodate up to two guests.
*Snowbirds Paradise* - Florida Keys
9.7 40 reviews
Florida Keys
20/06 – 27/06
$310/nighttotal: $2170 (7 )

*Snowbirds Paradise*

1 2
apartment , Marathon
This waterfront house in Marathon is just 800 metres from Crane Point Museum and Nature Center and 4 kilometres from Sombrero Beach, offering easy access to local attractions. The property enjoys excellent ratings for location, cleanliness and user experience.
The house has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private balcony, a garden, a tennis court, parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Islamorada's Anglers Reef- Remodeled Bathrooms-april Special - Florida Keys
10 63 reviews
Florida Keys
20/06 – 27/06
$597/nighttotal: $4179 (7 )

Islamorada's Anglers Reef- Remodeled Bathrooms-april Special

2 5
apartment , Islamorada, Village of Islands
This holiday home is located just 3km from Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park, offering easy access to the area's natural beauty and attractions. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The accommodation features two bedrooms, comfortably sleeping up to six guests. Enjoy amenities such as a private pool, spa tub, barbecue grill, and a fully equipped kitchen, perfect for relaxing and enjoying your stay.
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