Cruise And Resorts - Vacation Rentals in Florida Keys

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures From US $626
         

BEAUTIFUL STAY ON THE WATER From US $270
         

1.0 (14 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • View
Premium Floating Bungalow by Stay Ombi From US $1,417
         

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10.0 (1 Review)
Boat Rental
  • Air Conditioner
  • Parking
  • View
Waterfront Sunset View in the Aqua Villa Sand Dollar @ Mangrove Resort LLC From US $354
         

Affordable luxury yacht charters. From US $1,172
         

10.0 (49 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Living the Dream Key West Style From US $557
         

10.0 (43 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Ocean views! Luxury suites From US $638
         

10.0 (26 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Florida Keys

Over 10000+ Luxury Places to Stay in or Near Florida Keys
Little Bay Compound From US $16,123
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Florida Keys

Over 9869+ Top-Rated Vacation Rentals with a Pool in or Near Florida Keys
Almond Tree Inn Hotel - Adults Only From US $623
         

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10.0 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Florida Keys

Over 4366+ Pet-Friendly Vacation Rentals in or Near Florida Keys
Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Capmar House by Brightwild Huge Home Pool From US $1,828
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp From US $1,049
         

10.0 (81 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,335
         

9.8 (137 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Florida Keys

Over 2297+ Large Vacation Homes & Villas in or Near Florida Keys
Pelico Paradise From US $304
         

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9.6 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Atlantic View Luxury Villa with Pool From US $1,209
         

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10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,350
         

Conch style home in Oldtown with private pool AND dock! From US $1,560
         

Wheelchair Accessible Vacation Homes in Florida Keys

Over 2956+ Wheelchair Accessible Vacation Homes in or Near Florida Keys
Sunshine Key King Travel Trailer 4 From US $238
         

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8.9 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ From US $530
         

10.0 (162 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
The Islands of Islamorada From US $954
         

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9.8 (72 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Birds Eye Loft Perched Above the Marina 1BR 1BA 5413 From US $298
         

Top Floor unit with a ocean view! PRIVATELY OWNED From US $271
         

9.8 (131 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Florida Keys Vacation Rentals and Airbnb Places to Stay Under $200

Over 1142+ Florida Keys Vacation Rentals and Airbnb Places to Stay Under $200
Dolphin Retreat From US $162
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Canal-front condo with amazing views & convenient location From US $195
         

Suite Dreams Inn by the Beach From US $189
         

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8.4 (55 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • Balcony/Terrace
Luxurious Tropical Retreat with Private Tiki Hut From US $119
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Florida Keys

Over 9052+ Instantly Bookable Vacation Homes in or Near Florida Keys
el mirador From US $837
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pool

About Florida Keys Vacation Rentals

With more than 187 Florida Keys vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruiseandresorts and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Florida Keys.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruiseandresorts Florida Keys, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Florida Keys. Places to stay near Florida Keys are 195.09 ft² on average, with prices averaging $613 a night.

Cruiseandresorts makes it easy and safe to find and compare vacation rentals in Florida Keys with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Florida Keys

Type Count

Use these Quick Filters to Find a Vacation Rental in Florida Keys

Pro Tip: Cruiseandresorts makes it easy to compare the best listings on Cruiseandresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruiseandresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Florida Keys.

Weather in Florida Keys

View the weather forecast for Florida Keys before booking your Florida Keys Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Florida Keys Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Florida Keys?
How many vacation rentals are available in Florida Keys?

Currently, the total number of properties listed in 2026 is over 187 in the Florida Keys area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Florida Keys.