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
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
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!
Number of Guests: 10
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!
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!
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.

Number of Guests: 8
Number of Rooms: 4
Location: Key West
Type of Property: House
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
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!
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!
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
10. ~ MAISONS de LUXE ~ 2 Stunning Destination w/ Private Pool and Balconies
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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Dayna Brockbank is a travel and language-learning blogger who has lived around the world but has now settled in Nice, France. She speaks 3 languages at varying levels of fluency: Spanish, Italian, and French, and graduated with a Bachelor’s in Spanish Education. She and her husband focus on making travel part of life by living cheaply and traveling on a budget.