Vacation rentals in the Florida Keys - HomeToGo base64Hash Vacation rentals in the Florida Keys - HomeToGo

Vacation rentals in the Florida Keys

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Top 15 most Recommended Vacation Rentals in the Florida Keys

Discover your ideal Florida Keys vacation rental with real-time comparisons of 15,284 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Key Colony Beach
House ∙ 7 guests ∙ 3 bedrooms

Vacation home with hot tub, patio & pool

Key Colony Beach, Monroe County, Florida, United States
This waterfront house in Key Colony Beach features a pool, hot tub, kitchen, and family-friendly amenities for up to 7 guests.
from $288
per night
Outstanding(36 ratings)
from $288
per night
View deal
House Cudjoe Key
House ∙ 8 guests ∙ 4 bedrooms

House with 4 rooms for 8 persons

Cudjoe Key, Monroe County, Florida, United States
This house rental in Cudjoe Key welcomes pets and accommodates up to eight guests for an unforgettable getaway.
from $215
per night
Outstanding(2 ratings)
from $215
per night
View deal
House Key Colony Beach
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbeque & terrace

Key Colony Beach, Monroe County, Florida, United States
This waterfront house rental in Key Colony Beach offers a kitchen, parking, and pet-friendly space for up to six guests.
from $241
per night
Very good(12 ratings)
from $241
per night
View deal
Cabin Monroe County
Cabin ∙ 8 guests ∙ 2 bedrooms

Family-friendly cottage with garden, pool & barbeque | Dogs allowed

Monroe County, Florida, United States
This waterfront cabin in Monroe County offers a pool, sauna, spa, and spacious yard, perfect for family getaways with pets.
from $159
per night
from $159
per night
View deal
House Cudjoe Key
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped wonderful house with barbeque & patio

Cudjoe Key, Monroe County, Florida, United States
This Cudjoe Key house rental features a kitchen, balcony, and parking, accommodating up to 8 guests for an unforgettable getaway.
from $164
per night
Outstanding(23 ratings)
from $164
per night
View deal
House Key West
House ∙ 2 guests ∙ 1 bedroom

Fully equipped house with pool & terrace | Next to Southernmost Point | Pool view | Pets allowed

Key West, Monroe County, Florida, United States
This Key West house rental offers beach access, a pool, and pet-friendly amenities, perfect for a memorable getaway for two.
from $159
per night
Outstanding(1 rating)
from $159
per night
View deal
Condo Islamorada
Condo ∙ 12 guests ∙ 5 bedrooms

Condo with grill | Water view | Suitable for remote work

Islamorada, Monroe County, Florida, United States
This waterfront condo in Islamorada features a sea view, spa, kitchen, and balcony, perfect for gatherings of up to 12.
from $760
per night
Outstanding(3 ratings)
from $760
per night
View deal
Condo Marathon
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped condo with BBQ & pool | Next to the beach

Marathon, Monroe County, Florida, United States
This condo in Marathon features a pool, kitchen, balcony, and parking, accommodating up to 8 guests for an unforgettable getaway.
from $361
per night
Outstanding(24 ratings)
from $361
per night
View deal
House Marathon
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with pool, BBQ & patio

Marathon, Monroe County, Florida, United States
This waterfront house rental in Marathon features a pool, kitchen, and balcony, accommodating up to eight guests for a perfect getaway.
from $510
per night
Outstanding(15 ratings)
from $510
per night
View deal
House Key Colony Beach
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly wonderful vacation home with barbeque & pool | Water view

Key Colony Beach, Monroe County, Florida, United States
This waterfront house rental in Key Colony Beach features a pool, spa, and sea views, perfect for family gatherings or events.
from $297
per night
Outstanding(2 ratings)
from $297
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

House with yard, BBQ & pool

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada features a pool, balcony, and yard, plus space for six and a welcoming environment for pets.
from $285
per night
Outstanding(1 rating)
from $285
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, private pool & yard | Close to Duval Street | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a private heated pool, a kitchen, and pet-friendly accommodations for six guests.
from $188
per night
Outstanding(2 ratings)
from $188
per night
View deal
House Key Largo
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with barbecue & terrace

Key Largo, Monroe County, Florida, United States
This Key Largo house rental offers a balcony, kitchen, and parking, welcoming up to 10 guests and their pets for a memorable stay.
from $240
per night
from $240
per night
View deal
House Marathon
House ∙ 14 guests ∙ 4 bedrooms

Vacation home with yard, patio & jacuzzi | Good for workation

Marathon, Monroe County, Florida, United States
This waterfront house rental in Marathon features a hot tub, fireplace, and beach access, perfect for a family getaway of 14.
from $1,030
per night
Outstanding(28 ratings)
from $1,030
per night
View deal
Cabin Key West
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with private pool & BBQ | Near West Martello Tower | City view

Key West, Monroe County, Florida, United States
This Key West cabin features a private heated pool, balcony, and kitchen, accommodating up to four guests for an unforgettable stay.
from $181
per night
Outstanding(10 ratings)
from $181
per night
View deal

Vacation houses with Balconies or Patios

House  Marathon
from $211
per night
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented wonderful vacation home with barbeque | Water view | Dogs allowed

5.0
Outstanding(3 ratings)
Marathon, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Bahama Village
from $187
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with patio & barbecue | Next to Southernmost Point

Bahama Village, Key West, Florida, United States
Balcony/Patio
View deal
House  Monroe County
from $247
per night
House ∙ 9 guests ∙ 3 bedrooms

Children-friendly lovely vacation home with patio, hot tub & yard | Perfect for remote work | Pets allowed

4.9
Outstanding(12 ratings)
Monroe County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House  Key West
from $371
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented vacation home with barbeque, private pool & terrace | City view | Pets allowed

5.0
Outstanding(16 ratings)
Key West, Monroe County, Florida, United States
Yard
View deal
House  Key Largo
from $139
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly house with yard, terrace & barbeque | Nature view

4.7
Excellent(27 ratings)
Key Largo, Monroe County, Florida, United States
Yard
View deal
House  Islamorada
from $779
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with garden, patio & private pool | Nature view | Good for workation | Dogs allowed

4.8
Outstanding(95 ratings)
Islamorada, Monroe County, Florida, United States
Yard
View deal
See all offers

Vacation rentals and apartments with air conditioning

House  Big Pine Key
from $197
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented ample house with terrace & yard | Dogs allowed

4.4
Very good(10 ratings)
Big Pine Key, Monroe County, Florida, United States
Air conditioning
View deal
House  Key Largo
from $175
per night
House ∙ 7 guests ∙ 3 bedrooms

House with barbeque & terrace

5.0
Outstanding(12 ratings)
Key Largo, Monroe County, Florida, United States
Air conditioning
View deal
House  Key Largo
from $78
per night
House ∙ 6 guests ∙ 2 bedrooms

Spacious house with garden, barbecue & terrace

4.4
Very good(21 ratings)
Key Largo, Monroe County, Florida, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in the Florida Keys offering exceptional value for money

House Islamorada
from $726
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, barbeque & heated pool | Nature view | Perfect for remote work

5.0
Outstanding(53 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $392
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with private pool, BBQ & jacuzzi | Suitable for remote work

5.0
Outstanding(1 rating)
Islamorada, Monroe County, Florida, United States
View deal
House Key Haven
from $633
per night
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped wonderful vacation home with barbeque, jacuzzi & private pool | Perfect for remote work | Pets are welcome

5.0
Outstanding(2 ratings)
Key Haven, Monroe County, Florida, United States
View deal

Top-Rated Vacation rentals in the Florida Keys

Book the highest-rated Florida Keys vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Key Colony Beach
from $232
per night
House ∙ 6 guests ∙ 2 bedrooms

Child-friendly vacation home with pool & grill | Water view | Pets are welcome

5.0
Outstanding(2 ratings)
Key Colony Beach, Monroe County, Florida, United States
View deal
House Big Pine Key
from $224
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped vacation home with grill | Pets allowed

5.0
Outstanding(1 rating)
Big Pine Key, Monroe County, Florida, United States
View deal
Villa Marathon
from $364
per night
Villa ∙ 9 guests ∙ 4 bedrooms

Villa with patio, private pool & BBQ

5.0
Outstanding(156 ratings)
Marathon, Monroe County, Florida, United States
View deal

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in the Florida Keys

  • Pool (11,348)
  • Pet-friendly (5,176)
  • WiFi (13,503)
  • Air conditioning (14,021)
  • Kitchen (11,214)
  • Balcony/patio (7,522)
  • TV (13,414)
  • Fishing (7,806)
  • Washing machine (9,254)
  • Parking (659)
  • Grill (7,656)
  • Microwave (10,447)

More than two-thirds of the vacation rentals provide a pool, which makes Florida Keys an excellent destination for travelers looking to make a splash. In addition, more House rental have pools than any other type of property. They are an excellent choice if you go in a group of 7, as that is the number of people they can usually accommodate. nearly half of Florida Keys's vacation rentals offering a pool are located within two miles of water, divide your time between the pool and the waterfront

Price and Availability Index in the Florida Keys

Click on any bar to see price and availability information

Vacation Rental Price Information in the Florida Keys

This graph displays the average prices of vacation rentals and apartments in the Florida Keys. The week with the highest average prices is in December (12/26 – 1/2). During this week, a nightly price on average will be $990. You can find some of the best deals during the month of September (9/12 – 9/19). This period is usually the least busy and most affordable time of the year.

Rental availability information in the Florida Keys

Find out how busy the upcoming months are going to be in the Florida Keys using our availability graph. The week with the highest booking rate in the next 12 months is in February (2/28 – 3/7), where 65% of the vacation rentals are booked. Conversely, it is in June (6/6 – 6/13) that the highest percentage of rentals are available.

Sun, Beaches and Nature are Yours With a Florida Keys Vacation Rental

The Keys are an Archipelago in the southeast end of mainland Florida. There are in total more than 1,700 islands, and less than 5% of those are inhabited. The islands have unique flora and fauna and a warm climate throughout the year. It is a destination for travelers who wish to surround themselves with nature, enjoy the white sandy beaches of the islands or enjoy water sports. Florida Keys vacation rentals are a great way to discover and enjoy everything this perfect destination offers.

What are the best activities for families in the Florida Keys?

Toddlers, School Age, or Teenagers: Activities for All Ages

Visitors that are coming to stay in a Florida key vacation rental with kids will have many options for family-friendly activities. There are options for kids of all ages, from toddlers to teens.

The little ones will enjoy spending time at the Sheriff's Animal Farm, home to some unusual inhabitants including lemurs, emus and alligators. For younger or older teens, the Dolphin Research Center runs week-long camps based on their age range, where they can be introduced to dolphins and learn to about their behavior.

At the Key West Aquarium, guests can interact and feed marine life at the 'Touch Tank' or take a guided tour through the Turtle Hospital to learn how to help rescued marine life. However, the best way to see all the beautiful sealife the Keys has to offer is to hire a snorkle and take to the ocean.

Whether you choose to relax and enjoy the incredible surroundings, or take the family on a new adventure every day, staying in your Florida Keys vacation home creates a comfortable, more private experience for the entire family.

What are the top sights in the Florida Keys?

The 10 Best Beaches in the Florida Keys

1. Bahia Honda State Park: A 2.5-mile long beach with white sand, shallow turquoise water, and palm trees.

2. Sombrero Beach: This beach is situated on Marathon and offers white sands, amenities, a playground, and grassy lawns.

3. Harry Harris Park: A man-made beach that has sand shipped in when required. The nearby jetty provides protection, making this a safe place for children to swim.

4. John Pennekamp Coral Reef State Park: A small beach where you can easily swim to the reef from the beach and snorkel in the calm water.

5. Coco Plum Beach: This natural beach is a nesting site for endangered turtle species.

6. Higgs Beach: Here you'll find white sand, shallow water, and a number of activities such as volleyball.

7. Sandspur Beach: A small public beach with good snorkeling sites.

8. Smathers Beach: This beach has good launch sites kayakers.

9. Fort Zachary Taylor Beach: A popular beach for families as it has the safest swimming area in the Keys.

10. Dog Beach: The only beach in the Keys that allows unleashed dogs.

Where are the unique attractions in the Florida Keys?

Florida Keys Excursions: Ecotourism, Adventure Sports and Relaxation

Booking your Florida Keys vacation rental on any of the inhabited islands of the archipelago will give travelers the chance to discover uncharted nature, explore their adventurous side and a chance to relax on one of the many gorgeous beaches or spa resorts.

The Keys Islands also present visitors with a vast array of activities. They can spend the day exploring shipwrecks and reefs at Key Largo, go scuba diving and off-shore fishing at Islamorada. At the Florida Keys there is always an adventure on the horizon for those who seek it.

An opportunity to help the environment and enjoy nature will never be far from your Florida Keys vacation rental. At the National Key Deer Refuge volunteers are welcome through the year. They help maintain the Key deers, a species of small deer with white fury tails, that only exist in the Lower Keys. The program aims to keep the deer population growing and protected.

Ecotourists with experience diving can learn from marine scientists about the natural and human threats to the reefs, and help the effort to restore the corals to health. They can get involved helping marine ecosystems thrive, while experiencing some of the most beautiful sealife on the planet.

After a day of adventuring, or after all that hard work volunteering, it is time to take care of yourself. There are several spas located around they Keys, which offer varying health and wellness treatments. Pamper yourself with facials and manicures, relax at the hands of a trained masseuse or even join a yoga class on the beach.

What are the must-see attractions in the Florida Keys?

5 Best Things to Do in the Florida Keys During Your Stay

1. Harry S Truman Little White House

Built in 1890, the Truman Little White House was used as a naval command center during the Spanish-American War and both World Wars. After 1946, it was used as President Harry S Truman's winter White House.

2. Ernest Hemingway Home and Museum

The Ernest Hemingway Home and Museum lets visitors experience the place that inspired the writer during his most prolific period, and see the six-toed descendants of his many cats.

3. Dry Tortugas National Park

With sparkling waters and diverse coral and marine life, swimming, snorkelling, and diving at the Dry Tortugas National Park is a unique outdoors experience.

4. Turtle Hospital

Injured sea turtles found on Florida’s shores are brought here to convalesce. Visitors can learn about environmental challenges faced by these gentle creatures.

5. Key West Butterfly and Nature Conservatory

Home to countless butterflies, birds, and plants, the conservatory lets visitors study the animals or simply enjoy this glass-controlled habitat.

Information about vacation rentals in the Florida Keys

🏡 Vacation rentals available 15,284 rentals
🌙 Nightly prices starting at $119
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 5,298 homes
🏊 Vacation rentals with pools 11,714 homes
1,289 reviews
Florida Keys vacation rentals have an average rating of 4.2/5 on 1,289 reviews left by travelers.

Frequently Asked Questions

What is the typical price per night for a vacation home in the Florida Keys?

The price of a night's stay in the Florida Keys starts at $119. Nightly prices for house rentals are $754 on average. Condos in the Florida Keys cost on average $553 per night.

How many vacation rentals are available for booking in the Florida Keys?

There are currently 15,284 vacation rentals in the Florida Keys to choose from and book for your next trip.

What amenities are most popular for vacation homes in the Florida Keys?

If you're looking to book a vacation rental in the Florida Keys, travelers search for vacation homes with Pets allowed, Pool and Internet.

How many vacation homes with pools are in the Florida Keys?

Choose from 11,714 vacation rentals available in the Florida Keys.

Are dogs allowed in vacation homes in the Florida Keys?

Finding a vacation rental in the Florida Keys that allows pets is possible, with 5,298 pet-friendly available.

Find more vacation rental types in the Florida Keys

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