Florida Keys vacation rentals

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Latest Florida Keys vacation rental deals

MOST POPULARMiami
Vacation homes from C$ 58

Best Florida Keys vacation rentals

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C$ 30 - C$ 226C$ 226 - C$ 420C$ 420 - C$ 614C$ 614 - C$ 807C$ 807+ per night

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ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Florida Keys

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Tropical Cottages - Marathon - Patio
Tropical Cottages
Marathon, FL, United States
8.0Very good(565)
Parking
Free Wi-Fi
Pet friendly
C$ 166+
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Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters - Big Pine Key - Balcony
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
Big Pine Key, FL, United States
9.3Wonderful(6)
C$ 194+
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Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf - Big Pine Key - Living room
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
Big Pine Key, FL, United States
9.0Wonderful(4)
C$ 201+
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Yacht 33'~free Kayak - Key Largo
Yacht 33'~free Kayak
Key Largo, FL, United States
9.4Wonderful(30)
Free Wi-Fi
Pet friendly
C$ 202+
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Unique And Beautiful 'Bonne-Vie At Sea'Br - Key Largo - Kitchen
Unique And Beautiful 'Bonne-Vie At Sea'Br
Key Largo, FL, United States
10Wonderful(16)
Free Wi-Fi
C$ 219+
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Big Pine Key Dreams - Big Pine Key - Living room
Big Pine Key Dreams
Big Pine Key, FL, United States
10Wonderful(2)
C$ 271+
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Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key - Big Pine Key - Patio
Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key
Big Pine Key, FL, United States
10Wonderful(1)
C$ 275+
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Aqua Lodges at 47th Street - Marathon
Aqua Lodges at 47th Street
Marathon, FL, United States
8.5Very good(39)
Parking
Free Wi-Fi
C$ 285+
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Big Pine Key Paradise Canal front fenced yard. - Big Pine Key - Living room
Big Pine Key Paradise Canal front fenced yard.
Big Pine Key, FL, United States
9.2Wonderful(5)
Free Wi-Fi
Pet friendly
Spa
C$ 312+
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Dreams Come True - 75' Dock - 250 ' To Open Channel big Pine Key Fl - Big Pine Key - Kitchen
Dreams Come True - 75' Dock - 250 ' To Open Channel big Pine Key Fl
Big Pine Key, FL, United States
9.8Wonderful(11)
Free Wi-Fi
C$ 357+
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Newly Remodeled Corner House on the Water - Big Pine Key - Kitchen
Newly Remodeled Corner House on the Water
Big Pine Key, FL, United States
10Wonderful(3)
Free Wi-Fi
C$ 370+
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Lower Keys Retreat - Big Pine Key - Pool
Lower Keys Retreat
Big Pine Key, FL, United States
9.6Wonderful(16)
Free Wi-Fi
Pool
Pet friendly
C$ 387+
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Star Room at Barnacle Resort - Big Pine Key - Balcony
Star Room at Barnacle Resort
Big Pine Key, FL, United States
9.3Wonderful(11)
Parking
Free Wi-Fi
Pet friendly
C$ 481+
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Pool and Canal Home - Big Pine Key - Living room
Pool and Canal Home
Big Pine Key, FL, United States
9.8Wonderful(16)
Free Wi-Fi
C$ 596+
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Pool! Stunning New Oceanfront 4 Bedroom 3+ Acre Private Estate - Big Pine Key - Kitchen
Pool! Stunning New Oceanfront 4 Bedroom 3+ Acre Private Estate
Big Pine Key, FL, United States
10Wonderful(1)
Free Wi-Fi
C$ 710+
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Keys 3 Bedroom Corner Home near Beach & Key West - Big Pine Key
Keys 3 Bedroom Corner Home near Beach & Key West
Big Pine Key, FL, United States
7.8Good(10)
Free Wi-Fi
C$ 807+
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Booking Insights

KAYAK’s insights for vacation rentals in Florida Keys

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Florida Keys with confidence.

What is the cheapest day of the week to book a vacation rental in Florida Keys?

Monday offers the lowest rates in Florida Keys, with an average nightly price of C$ 503. The highest prices are found on Wednesday, with average rates at C$ 760.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

September
July
C$ 436
C$ 483
Cheapest month to stay with an average 33% drop in price.
Most expensive month to stay with an average 61% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Florida Keys vacation rental

  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Florida Keys for 5 days.
  • Vacation rentals in Florida Keys are around 8% more expensive than hotels on average. Search here to compare prices for all accommodation types in Florida Keys.
  • The city in Florida Keys with the most affordable vacation homes is Miami, with around 6,165 properties and an average price of C$ 205. The most popular vacation rentals in Florida Keys among KAYAK users are Habitat Brickell by Sextant, Global Luxury Suites Miami Worldcenter, and Nomada Residences.

FAQs when booking a vacation home in Florida Keys

  • How much is a vacation rental in Florida Keys for tonight?

    In the last 72 hours, users have found Florida Keys vacation rentals for tonight for as low as C$ 120. Search here for similar prices

  • How much is a vacation rental for a week in Florida Keys?

    The average price for a weekly Florida Keys vacation rental found by KAYAK users in the last 2 weeks is C$ 1,399.

  • How much is a vacation rental for a month in Florida Keys?

    The average price for a monthly Florida Keys vacation rental found by KAYAK users in the last 2 weeks is C$ 5,995.

  • What types of vacation rentals are available in Florida Keys?

    There are loads of different property types that you can make your vacation home in Florida Keys. You’ll find condos, apartments, bungalows, cabins, campgrounds, caravans, cottages, houses, lodges, recreational vehicles, houseboats, vacation villages, villas, homestays, towers, boats, hotels, agritourism, chalets, guest houses, luxury tents and caravan parks.

  • What are some of the most-loved vacation rentals available in Florida Keys?

    There are many types of properties available for Florida Keys vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Tropical Cottages and Sun Outdoors Key Largo.

  • Are there any pet-friendly vacation rentals in Florida Keys?

    There are a number of dog and pet-friendly Florida Keys vacation rentals, with around 14% allowing you to bring your pet along with you.

Where to stay in Florida Keys?

Our map will help you find the perfect place to stay in Florida Keys by showing you the exact location of each vacation home.

What Florida Keys vacation rental guests are talking about

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Popular topics

Vacation rentals by topic

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Habitat Brickell by Sextant - Miami
Habitat Brickell by Sextant
Brickell
8.1Very good(1423)
Free Wi-Fi
C$ 150+
Check availability
Hudson House - Miami
Hudson House
Miami, FL, United States
8.2Very good(685)
Free Wi-Fi
C$ 17+
Check availability
Four Ambassadors Apartments - Miami
Four Ambassadors Apartments
Brickell
7.8Good(151)
Free Wi-Fi
C$ 205+
Check availability

Everything you need to know for your stay in Florida Keys

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