Find short term rentals in Florida Keys at the best prices

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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

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball - Florida Keys
10 44 reviews
Florida Keys
26/12 – 03/01
$3041/nighttotal: $24328 (8 )

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball

4 10
apartment , Key Largo
This five-bedroom, three-bathroom Key Largo oceanfront condo, situated within the Mariner's Club, offers unparalleled access to Molasses Reef and is adjacent to the community marina and pool.
The 10-guest property boasts a terrace, garden, swimming pool, spa, tennis court, and full kitchen, plus proximity to John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
Beautiful And Cozy 3- Bedroom Townhouse - Florida Keys
10 36 reviews
Florida Keys
27/06 – 04/07
$338/nighttotal: $2366 (7 )

Beautiful And Cozy 3- Bedroom Townhouse

3 2
apartment , Florida City
This peaceful family-friendly house is located in Florida City, just a short drive from the Florida Keys Outlet Marketplace and the Navy Wells Pineland Preserve, offering a blend of shopping and nature exploration. It has been rated excellent by previous guests, making it a popular choice for families and groups.
The house has three bedrooms and three bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking, ensuring a comfortable and enjoyable stay.
Casa Pilar At Seaglass Cove - Florida Keys
Florida Keys
26/12 – 03/01
$5348/nighttotal: $42784 (8 )

Casa Pilar At Seaglass Cove

5 10
apartment , Marathon
This oceanfront flat, named Casa Pilar, is situated within the exclusive SeaGlass Cove gated community in Marathon, offering direct Atlantic views and convenient access to marinas, Sombrero Beach, and Curry Hammock State Park.
This residence boasts a chef's kitchen, an ocean-view terrace with an outdoor kitchen, an on-site elevator, and access to a communal resort-style pool and pickleball court, with a 30-foot boat slip included for weekly stays through 2025.
Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views! - Florida Keys
8.8 5 reviews
Florida Keys
26/12 – 03/01
$3156/nighttotal: $25248 (8 )

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

4 10
apartment , Marathon
This luxurious waterfront property in Marathon, Florida Keys, boasts a 73-foot private dock, offering direct access to boating and fishing, and is minutes from Coco Plum Beach.
This spacious 177 square metre holiday home features four en-suite bedrooms, sleeping up to ten guests, a private pool, BBQ, games area, and ample amenities including high-speed Wi-Fi, a fully equipped kitchen, and parking for four cars plus a boat trailer.

Best Florida Keys lodging with a balcony

Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar - Florida Keys
9.7 127 reviews
Florida Keys
01/09 – 04/09
$421/nighttotal: $1263 (3 )

Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar

2 2
apartment , Tavernier
This waterfront apartment is situated in Tavernier, just a 2.4km walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and scenic location close to the area's attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment spans 87 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. It features a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families or groups seeking a relaxing and enjoyable stay.
Beachside Unit 29 - Key Colony - Florida Keys
9.7 121 reviews
Florida Keys
04/08 – 07/08
$446/nighttotal: $1338 (3 )

Beachside Unit 29 - Key Colony

1 4
apartment , Key Colony Beach
This apartment is located in Key Colony Beach, just a 10-minute walk from Sunset Park Beach and Coco Plum Beach, offering easy access to the beautiful white sands and turquoise waters of the Florida Keys. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat has a floor area of 43 square metres and can accommodate up to 4 guests. It comes with a fully equipped kitchen, a balcony, a swimming pool, and parking, allowing you to enjoy a comfortable and convenient stay.
Vacation Day Is Always A Great Idea! 4 Classy Units, Free Parking, Pets Allowed! - Florida Keys
Florida Keys
26/12 – 03/01
$3505/nighttotal: $28040 (8 )

Vacation Day Is Always A Great Idea! 4 Classy Units, Free Parking, Pets Allowed!

4 10
apartment , Islamorada, Village of Islands
This Islamorada beachfront property offers four uniquely decorated hotel rooms, each 28 square metres, centrally located and providing easy access to attractions such as the History of Diving Museum and Keys History & Discovery Centre.
The 112-square-metre self-catering property sleeps up to 16 guests, boasting a private boat ramp (fee applies), heated pool, daily continental breakfast, and proximity to Islamorada Brewery & Distillery and Florida Keys Brewing Co., alongside water sports opportunities.
Beach View Unit In Islamorada! Pets Allowed, Parking, Pool! - Florida Keys
8.6 25 reviews
Florida Keys
04/08 – 07/08
$314/nighttotal: $942 (3 )

Beach View Unit In Islamorada! Pets Allowed, Parking, Pool!

1 4
apartment , Islamorada, Village of Islands
This Islamorada beachfront apartment, part of a pet-friendly resort, offers direct beach access and partial ocean views from its 28-square-metre (301 sq ft) balcony, conveniently located near the Islamorada Brewery & Distillery and Indian Key Historic State Park.
The self-catering flat features two queen beds sleeping four, a fully equipped kitchenette including a fridge, microwave, and dishwasher, plus daily housekeeping and continental breakfast; on-site amenities include a heated pool, kayaks, paddleboards, and bike rentals.

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

Waterfront Islamorada Condo  Heated Pool, Marina & Deeded Boat Slip - Florida Keys
10 67 reviews
Florida Keys
27/06 – 04/07
$423/nighttotal: $2961 (7 )

Waterfront Islamorada Condo Heated Pool, Marina & Deeded Boat Slip

2 2
apartment , Islamorada, Village of Islands
This Islamorada condominium is situated at mile marker 88.5, offering convenient access to Robbie's Marina and the Theater of the Sea, with Miami located 108 kilometres to the north.
This family-friendly apartment, measuring 88 square metres and accommodating up to six guests, features two bedrooms and two bathrooms, a fully equipped kitchen with granite countertops, a private balcony with pool views, direct access to a deeded boat slip (#49), and resort-style amenities including a heated swimming pool and pickleball courts.
Beachside Unit 14 - Key Colony - Florida Keys
9.7 132 reviews
Florida Keys
01/09 – 04/09
$442/nighttotal: $1326 (3 )

Beachside Unit 14 - Key Colony

1 2
apartment , Key Colony Beach
This apartment is situated in Key Colony Beach, a short 1.6km walk from Sunset Park Beach and Coco Plum Beach, and within 3.2km of Curry Hammock State Park, known for its peaceful and relaxed atmosphere. The apartment has received excellent ratings for its location, cleanliness and overall experience.
This self-catering property has 1 bathroom and is 43 square metres in size, comfortably sleeping 2 guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden and parking, as well as internet access and pet-friendly facilities.
Sombrero Getaway Poolside Retreat With Canal Views - Florida Keys
9.7 14 reviews
Florida Keys
26/12 – 03/01
$1692/nighttotal: $13536 (8 )

Sombrero Getaway Poolside Retreat With Canal Views

1 10
apartment , Marathon
This canal-front house in Marathon, Florida offers direct access to the waterway and is conveniently located near various attractions, though precise distances aren't provided.
Sleeping up to ten guests, this four-bedroom, three-bathroom property boasts a private dock, swimming pool, fully equipped kitchen, and high-speed Wi-Fi, alongside ample parking.
Casa Seagulls - Florida Keys
9.8 45 reviews
Florida Keys
27/06 – 04/07
$429/nighttotal: $3003 (7 )

Casa Seagulls

1 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is situated in Islamorada, directly overlooking the Atlantic Ocean, within walking distance of fishing, snorkeling, diving, and kayak/paddleboard rentals. Local charters for these activities are about 1.6 kilometres away. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This comfortable property can sleep up to four adults and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a garden, a fitness centre, and parking. Guests can enjoy stunning ocean views from the spacious porch, relax by the pool, or barbecue on the beach.

Best Florida Keys lodging with laundry available

Waterfront Dock Pool Penthouse Near Duval St - Florida Keys
9.8 498 reviews
Florida Keys
24/07 – 27/07
$4030/nighttotal: $12090 (3 )

Waterfront Dock Pool Penthouse Near Duval St

4 14
apartment , Key West
This Key West penthouse condo, located in the historic downtown area less than 1.6km from Duval Street and close to attractions such as the Historic Seaport and Hemingway House, offers breathtaking waterfront views.
The 172 square metre property boasts four bedrooms, four bathrooms, sleeping up to sixteen guests, and includes a private boat slip (up to 35ft), a heated pool, and a full kitchen; on-site amenities also include a tiki bar & grill and bike rentals.
Key Colony Beach Paradise - Florida Keys
9.4 6 reviews
Florida Keys
26/12 – 03/01
$1189/nighttotal: $9512 (8 )

Key Colony Beach Paradise

4 10
apartment , Key Colony Beach
This four-bedroom house is situated in Coury, a quiet neighbourhood just 800 metres from Sunset Park Beach and within 5 kilometres of attractions such as the Marathon Visitor Centre and Curry Hammock State Park.
The 215 square metre property boasts a private pool, a terrace, a garden and parking, comfortably accommodating up to 10 guests.
Apartment ∙ 8 Bedrooms ∙ 16 Guests - Florida Keys
Florida Keys
24/07 – 27/07
$5494/nighttotal: $16482 (3 )

Apartment ∙ 8 Bedrooms ∙ 16 Guests

8 14
apartment , Key West
This luxurious eight-bedroom house is located in a gated community within the Modern Keys area of Key West, offering easy access to boat ramps in Key Haven and Stock Island.
The property boasts eight king-size bedrooms each with an ensuite bathroom, accommodating up to 16 guests, and features a fully equipped kitchen, private fenced yard, and convenient amenities including high-speed internet and access to a local gym; private boat excursions and chauffeur services are also available.
Tidelands House At Lunara Bay - Florida Keys
9.6 4 reviews
Florida Keys
24/07 – 27/07
$5352/nighttotal: $16056 (3 )

Tidelands House At Lunara Bay

8 14
apartment , Key West
This waterfront property in Lunara Bay, a gated community less than 1 kilometre from Key West, offers private boat docking for vessels up to 40 feet and is situated close to the Ernest Hemingway Home and Museum and Southernmost Point.
This substantial 372 square metre residence accommodates up to 16 guests across eight en-suite bedrooms, featuring a private swimming pool, fenced garden, and complimentary gym access at FYT, with optional private boat excursions and chauffeur services available.
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