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The Best Florida Keys Luxury Vacation Rentals

There’s no place like the Florida Keys for a luxury vacation rental. From Key Largo to Key West, there are plenty of options for those looking to enjoy the sun and sand in style.

Florida Keys Luxury Vacation Rentals

There are lots of Florida Keys luxury vacation rentals to choose from so I’ve narrowed it down to the top ten. The luxury vacation homes all have over 70 reviews, over a 4.8-star rating, and all have private pools!

1. ~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in FL Keys

FL Keys Vacation Rentals
Photo Credit: VRBO

Number of Guests: 8

Number of Rooms: 4

Location: Key West

Type of Property: House

Average Nightly Price: $2,081

Amenities:

  • Swimming pool
  • Internet
  • Air conditioning
  • TV
  • Satellite or cable
  • Washer & dryer
  • Parking
  • No smoking
  • Heater

2. **NOONA’S MANSION @ THE ANNEX** Florida Keys vacation rentals

Luxury Vacation Rentals in the Keys
Photo Credit: VRBO

Number of Guests: 8

Number of Rooms: 6

Location: Key West

Type of Property: House

Average Nightly Price: $2,809

Amenities:

  • Washer & dryer
  • Air conditioning
  • TV
  • Satellite or cable
  • No smoking
  • Heater
  • Internet
  • Parking
  • Swimming pool
  • Accessible

3. 3 Story tropical Paradise conch style luxury rentals with private pool AND oceanfront!

Keys best Luxury Rentals
Photo Credit: VRBO

Number of Guests: 10

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Number of Rooms: 4

Location: Key West

Type of Property: House

Average Nightly Price: $1,408

Amenities:

  • Air conditioning
  • Satellite or cable
  • No smoking
  • Washer & dryer
  • TV
  • Wireless Internet
  • Parking
  • Swimming pool

4. Secret Luxury Villa @ Old Town with Private Pool, close to Duval!

Key West Vacation Rentals
Photo Credit: VRBO

Number of Guests: 6

Number of Rooms: 3

Location: Key West

Type of Property: Villa

Average Nightly Price: $1,175

Amenities:

  • Swimming pool
  • Internet
  • Air conditioning
  • TV
  • Satellite or cable
  • Washer & dryer
  • Parking
  • No smoking
  • Heater

5. Luxury Ocean Views home with private pool AND dock front home near marina!

Private pool villa in Key West
Photo Credit: VRBO

Number of Guests: 8

Number of Rooms: 3

Location: Key West

Type of Property: Townhome

Average Nightly Price: $1,097 (Best Deal!)

Amenities:

  • Air conditioning
  • Satellite or cable
  • No smoking
  • Washer & dryer
  • Grill
  • Pets welcome
  • TV
  • Internet
  • Parking
  • Swimming pool
  • Dining area

6. ~ GRAND MAISON Getaway ~ Solitude home on Duval St with pool and 4 ensuite bedrooms.

pool luxury rental Florida
Photo Credit: VRBO

Number of Guests: 8

Number of Rooms: 4

Location: Key West

Type of Property: House

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Average Nightly Price: $1,709

Amenities:

  • Satellite or cable
  • Air conditioning
  • TV
  • No smoking
  • Parking
  • Washer & dryer
  • Bathroom
  • Internet
  • Pets welcome
  • Living area
  • Swimming pool

7. **CONCH CASA GRANDE Rental Homes** Home+ Pool Walking Distance to Duval

Large VRBO for rent
Photo Credit: VRBO

Number of Guests: 8

Number of Rooms: 5

Location: Key West

Type of Property: House

Average Nightly Price: $2,239

Amenities:

  • Washer & dryer
  • Air conditioning
  • TV
  • Satellite or cable
  • No smoking
  • Heater
  • Internet
  • Parking
  • Swimming pool
  • Accessible

8. Oversized Oldtown home for the whole family with a private pool and boat dock with water views!

Luxury house with dock in the Keys
Photo Credit: VRBO

Number of Guests: 12

Number of Rooms: 5

Location: Key West

Type of Property: House

Average Nightly Price: $1,645

Amenities:

  • Air conditioning
  • Satellite or cable
  • No smoking
  • Washer & dryer
  • Deck
  • Pets welcome
  • TV
  • Internet
  • Parking
  • Swimming pool
  • Hot tub (spa)

9. Extra large Conch style home in Oldtown with private pool AND boat dockage for easy access!

Private rental in Key West
Photo Credit: VRBO

Number of Guests: 10

Number of Rooms: 4

Location: Key West

Type of Property: House

Average Nightly Price: $1,236

Amenities:

  • Air conditioning
  • Satellite or cable
  • Master Bedroom
  • No smoking
  • Washer & dryer
  • Porches
  • TV
  • Internet
  • Parking
  • Swimming pool
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10. ~ MAISONS de LUXE ~ 2 Stunning Destination w/ Private Pool and Balconies

Beautiful balcony home
Photo Credit: VRBO

Number of Guests: 12

Number of Rooms: 4

Location: Key West

Type of Property: House

Average Nightly Price: $2,137

Amenities:

  • Satellite or cable
  • Air conditioning
  • TV
  • No smoking
  • Parking
  • Washer & dryer
  • Patios
  • Internet
  • Pets welcome
  • Swimming pool
  • Waterfront home
  • Heater

Florida Keys Rentals

There are over 800 Keys (small islands) in the Florida Keys. Some of the most famous ones are Key West, Key Largo, Marathon, Islamorada, Big Pine Key, Duck Key, Grassy Key, and Cudjoe Key. Most of the luxury rentals are in Key West which is the last Key of the Florida Keys.

Whether you’re looking for a relaxing getaway or a fun-filled vacation, the Florida Keys has something for everyone. With so many luxurious vacation rental properties available, you’re sure to find the perfect place to call home away from home.

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