7 Luxury Rentals In Florida Keys, Florida - Updated 2022

luxury rental in florida keys

The Florida Keys are a stretch of tropical islands located off the southern coast of Florida. It is a coral cay archipelago which forms the southernmost portion of the United States. This place is known for tons of recreational activities such as fishing, boating, snorkeling and scuba diving. It is a great place to spend a quick and relaxing getaway with friends and family. The picturesque landscapes coupled with the exotic climate makes this place a major crowd puller during the holiday season. Take a look at some of the most value for money and luxurious vacation rentals in Florida Keys, Florida.

1. Superb luxury apartment with fabulous amenities (from USD 296)

This gorgeous apartment has everything you could want in a vacation rental. It is oozing with utmost comfort and is located in a supremely tranquil neighborhood. It is located in the Casa Marina East district of Key West which is equidistant to the beach and to the Old Town. With exquisite French decor, the interiors are very well done up and showcase elegance and utmost charm. The swimming pool area here is super spacious and is the perfect place to spend a relaxing evening. The other amenities provided here include air-conditioning, a washer and dryer, a swimming pool, parking facilities, internet connection and lots more.

2 reviews
House 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 27
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the upstairs master bedroom had a large attached office
My parents stayed in the downstairs bedroom
Their was plenty of space for all six of us
And the pool was lovely
It was big and warm and the kids had hours of fun jumping in the deep end
so my husband could work remotely and my children shared the third bedroom which was also upstairs
We were traveling with three generations (my parents me and my husband and my two young children)
The house was set up perfectly for us
Read more reviews

2. Stunning house in a gulf front property (from USD 1850)

Located in the midst of lush greenery, this fabulous property will ensure you have a delightful vacation. It offers breathtaking views of Everglades National Park which is famous for backcountry fishing. The apartment is easily accessible to the Snake Creek or Tavernier Creek as well as deep sea fishing or scuba diving in the Atlantic Ocean. The apartment offers some great facilities such as a recreational room, a swimming pool, internet access, TV, parking facilities, high-tech appliances, a washer, a dryer, and a fireplace.

Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks
Islamorada, FL, US
House 8 Guests 4 Bedrooms 4 Bathrooms

3. Gorgeous vintage cottage in the heart of Old Town, Key West

Located in one of the most popular areas of Old Town, Key West, this luxury cottage is the ideal getaway for a squad of four. The interiors are tastefully decorated with open beam ceilings and muted tiles. The bathroom and kitchen are oozing with extravagance and with exquisite decor and appliances. There is a spacious courtyard outdoors which sports some of the prettiest flowers, making it a view worth remembering. The location is to die for as well with all the major attractions at your disposal. Famous restaurants, art galleries, bakeries, coffee shops, jazz clubs are all within the vicinity. The amenities offered here include a swimming pool, a washer and dryer, air-conditioning, TV access, and internet facilities.

Vintage Luxury Cottage ~ Hidden Duval Street Location - Private Pool
19 reviews
House 4 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The fan overhead in the bedroom was nice to have on at night; however it was not totally secured/stable to the ceiling
There is a parking space in front of the property and one can easily reach any place in the old town on foot
Very private just off the quiet end of Duval Perfect size for a couple - could have four people but might be a little cramped
The property was excellent loved hanging by the private pool
The outdoor dining area under the porch could have been made more comfortable with the addition of pads on the chairs and the adjoining sitting area under the porch would have been more enjoyable w...
The pool was clean and very relaxing
Everything was spotlessly clean and we enjoyed daily swims in the pool and dinners on the terrace
the heated pool was amazing
it took us literally until the end of our trip to figure out where to put the trash and recycling bags outside
We are trying to figure out how we can get back for another week
we all did have a great time
a couple of times Had problems with the dryer but they are in the middle of repairing
Restaurants and shops are a short stroll away
The location was great close walking distance to everything
The property manager Paige addressed it right away and got it fixed the next day (on a Saturday)
the Luxury Vintage Cottage is the perfect place to stay at in Key West
We rented bikes from Fury around the corner
Read more reviews

4. Charming and relaxing villa

This gorgeous luxury villa is an abode of great amenities and offers mesmerizing ocean views. It is situated at a great location and has been renovated with all the necessities that one would need for a hassle-free stay. The bedrooms are oozing with comfort and are perfectly equipped with large king-sized beds and ceramic tile floors. The house is simply decorated and is sparkling clean. The rental is close to all the major attractions of the area. Some of the facilities offered here include air-conditioning, a heater, a washer and dryer, internet access, a TV and parking facilities.

Tropical Paradise-Pool- Steps to Beach
18 reviews
House 6 Guests 3 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
to have our very own pool in the backyard
The house is well-equipped and up to date
I felt like I was on a month long retreat
the proximity to the airport is an extra bonus (6 minutes)
was so relaxing the privacy perfect
The pool area is exactly as pictured
Bruce was a wonderful host and very responsive
Mardee could not have been more helpful
either and very well-maintained
the caretaker is more than helpful and a wealth of information
We've been pretty happy with all our rentals all through VRBO
it's really in a great location
Not a bad morning or afternoon walk to Duval Ability to walk (about 7 minute stroll) to beach every evening
and it's easy to get anywhere quickly
It's not far from grocery and other stores on Roosevelt Blvd
Cuban Coffee Queen also makes lousy coffee
Read more reviews

5. Modern and fully equipped apartment

Located on Sunrise Cay, this luxurious apartment for 12 is cost-efficient and is super comfortable as well. It is centrally located and fully equipped with all the facilities one would need for a delightful stay. The four bedrooms here are super spacious and the interiors are very well done up. They are modern and contemporary with intricate detailing to accentuate the whole setting. The house offers other luxurious facilities such as a fitness center, a recreation room with a pool table, ping pong, flat screen TV’s, barbeque facilities, an elevator, internet, and parking as well.

MODERN 3/3 IN VERY BEST LOCATION! Steps To Beach, Restaurants, Marina.
Key Largo, FL, US
House 8 Guests 3 Bedrooms 3 Bathrooms

6. Outstanding beach villa with panoramic views

This swanky four bedroom villa is oozing with utmost luxury and comfort. It has a phenomenal location and offers mesmerizing ocean and beach views. The interiors are tastefully decorated and the rooms are fully equipped with sky-high ceilings, gourmet kitchens, magnificent balconies and lots more. Besides this, the other amenities offered include a heated pool and spa, internet connection, air-conditioning, a washer and dryer, parking facilities, central heating, and TV.

Remarkable Oceanfront Estate in Islamorada
89051 Old Hwy
2 reviews
House 10 Guests 4 Bedrooms 5 Bathrooms

7. Centrally located apartment for eight

centrally located apartment for eight
Source: Vrbo

This five-star beach house has been a major crowd puller right since its inception and is the ideal accommodation for large groups of eight people. It has a fantastic location and is just minutes away from the gorgeous beach, the marina and lip-smacking eateries. The high-quality beds coupled with the fancy features will make every penny worthwhile. The house is equipped with high-tech, modern amenities such as large-screen TVs, a home theatre, a wine fridge, a huge island seating at the kitchen bar, air-conditioning, internet connection, hot tub, parking facilities, a washer, and a dryer.

Luxury Shark Key waterfront home with beach 10 minutes from downtown Key West
Key West, FL, US
8 Guests 3 Bedrooms 4 Bathrooms

A relaxing getaway

The Florida Keys is truly a magnificent place to feel absolutely relaxed and rejuvenated. The luxurious vacation rentals mentioned above will surely make your stay delightful with the best of amenities and facilities at your disposal.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

 Want to contribute as a Local Expert?
Explore Florida Keys
Good things are meant to be shared!