The 10 Best Luxury Resorts in the Florida Keys and Key West (2022)


Located at the southern tip of the Florida peninsula, the Florida Keys is comprised of more than 1,700 islands that separate the Atlantic Ocean from the Gulf of Mexico.  Every year more than 5 millions visitors travel to the Florida Keys and Key West to enjoy their tranquil waters, historical & natural sites and its relaxing atmosphere.

In this article we are going to list what we feel are the best luxury resorts in the Florida Keys and Key West.  In determining our list we were looking for high quality accommodations, amazing amenities & dining options as well as fantastic locations.

If you thinking about staying any of these amazing hotels, we would appreciate if you can use our links when making the reservations. Endless Summer is an affiliate with Expedia.com, Marriott and Hilton; we receive a small commission for each stay that was referred by our website. 

The 10 Best Luxury Hotels and Resorts in the Florida Keys & Key West (2022)

  • Casa Marina Key West
  • Cheeca Lodge and Spa
  • Hawks Cay Resort
  • Playa Largo Resort & Spa
  • Bungalows Key Largo
  • Little Palm Island Resort & Spa
  • Reefhouse Resort and Marina
  • The Reach Hotel Key West
  • Sunset Key Cottages Resort
  • Baker’s Cay Resort Key Largo

The Casa Marina Key West

The Casa Marina Resort in Key West is part of the Curio Collection by Hilton.  This 311-room resort has a very unique history.  During the 1950’s, the Casa Marina was used during World War II as an officers quarters.

Amenities at the Casa Marina include 1,100 feet of private beach, two outdoor resort style pools, on-site equipment rentals, resort activities, the on-site Spa al Mare and access to the fitness center of the resorts sister property (The Reach Key West Resort).  Dining options at the hotel range from grab-and-go to resort casual dining.

Nightly rates vary during the year but typically range from around $650 per night to more than $1,700 per night depending on the room type. If you are a Hilton Honors member you can use points for your stay – we found that starting from 200,000 points per night are needed for a free night stay at this hotel.

Click here for rates and reservations at the Casa Marina Key West

Checca Lodge and Spa

The 214-room Cheeca Lodge and Spa is an amazing AAA Four-Diamond resort that is located on Islamorada in the middle keys.  This 27-acre resort is one of the finest in all of the keys and perfect for next visit to the Florida Keys.

Amenities are extensive and include over 1,200 feet of private beach with a 525-foot fishing pier and extensive water sports activities, three outdoor pools, a Jack Nicklaus 9-hole par 3 golf course, a comprehensive program for kids and an on-site spa with fully equipped fitness studios.  There are also three restaurants, an oceanfront tiki bar and poolside dining venues offered at the Cheeca Lodge.

Nightly rates vary during the year but typically range from around $450 per night to more than $1,500 per night depending on the room type and location.

Click here for rates & reservations at the Cheeca Lodge

Hawks Cay Resort

One of the most popular resorts in the Florida Keys is Hawks Cay resort which is a AAA Four-Diamond Award winner.  This 60-acre, 427-room property is located on Duck Key in the middle and underwent a comprehensive $50 million renovation in 2018. The main hotel features 177 guestrooms to accompany the 250 two- and three-bedroom villas.

Amenities include a saltwater lagoon, five outdoor swimming pools, on-site watersports activities, fishing charters, eight lighted tennis courts, children’s activities, the 7,000 square foot Hawk’s Cay Calm Waters Spa, a full service marina and the on-site Dolphin Connection where guests can swim/interact with live dolphins in their natural habitat.

Nightly rates vary during the year but typically range from around $450 per night to more than $850 per night depending on the room type and location.

Click here for rates & reservations at Hawks Cay Resort

Playa Largo Resort & Spa

One of the most popular resort hotels throughout the Florida Keys is the Playa Largo Resort & Spa. Situated on 14.5-acres of secluded waterfront shoreline, the resort is located at mile marker 97 in Key Largo just a short drive to the John Pennekamp Coral Reef State Park.  This amazing 177-room resort features a variety of traditional guest rooms, suites, bungalows and a beach house.

Amenities at the Playa Largo Resort & Spa include a private beach overlooking Florida Bay with a number of water sports activities and a beach fire pit, heated resort style pool with private cabanas, a fully equipped fitness center, business center and the on-site Ocean Spa.  In addition, there is also a private marina and boat launch ramp directly on-site at the resort.  Dining options are range from resort casual to fine dining restaurants.

Nightly rates vary during the year but typically range from around $750 per night to more than $3,000 per night depending on the room type. If you are a Marriott Bonvoy member you can use points for your stay. Category 7 hotels like the Playa Largo Resort & Spa require 50,000 points during off peak nights, 60,000 during standard nights and 70,000 during peak nights.

Click here for rates & reservations at the Playa Largo Resort

Bungalows Key Largo

The Bungalows Key Largo features 135 single story bungalow cottages on a 12-acre waterfront property.  This adults only all-inclusive resort and includes unlimited food and alcoholic beverages as well as non-motorized water toys. Located near the John Pennekamp Coral Reef State Park this resort is highly unique to the Florida Keys.

Amenities at the Bungalows include two outdoor pools with oceanfront cabanas, water sports including snorkeling & paddle boarding and an Asian inspired spa.   There are three on-site restaurants which range from resort casual to fine dining venues.

Nightly rates vary during the year but typically range from around $1,500 per bungalow double occupancy.

Click here for rates & reservations at the Bungalows Key Largo

Little Palm Island Resort & Spa

One of the most luxurious resorts on our list is the Little Palm Island Resort & Spa.  This 4.5-acre intimate resort is located on Little Tour Key in the lower keys and is an adults only paradise.  Completely renovated in 2020, access to the 30-room resort is available only by boat or seaplane and is limited to 60 guests at a time.

Guests stay in thatched roof bungalows that have outdoor patios & showers, tropical décor and magnificent ocean views.  Amenities include a resort pool with cabanas, private beaches, plenty of watersports activities and the on-sites SpaTerre.

Nightly rates vary during the year but typically range from around $1,200 per night to more than $2,000 per night.

Click here for rates & reservations at the Little Palm Island Resort & Spa

Reefhouse Resort & Marina

The Reefhouse Resort & Marina is a 153-room hotel that is situated on a picturesque 17-acre waterfront property.  Located in the upper keys, this resort is a short distance to local area attractions like the John Pennekamp Coral Reef State Park.

Amenities include a small man made beach area, headed outdoor pool, 24-hour fitness center, small marina/dive shop and on-site resort spa.  There is also more than 50,000 square feet of indoor & outdoor event space which is perfect for weddings, family reunions and small business conferences.

Nightly rates vary during the year but typically range from around $400 per night to more than $800 per night depending on the room type. 

Click here for rates & reservations at the Reefhouse Resort and Marina

The Reach Hotel Key West

The Reach Key West is part of the Curio Collection by Hilton.  This 200-room property is located on 13-beachfront acres in the upper Florida Keys.  It is one of the most tranquil hotels on our list, perfect for a relaxing weekend getaway.     

Amenities at The Reach include an outdoor pool, natural sand beach area with a number of water sports experiences (paddleboard, snorkeling,  kayakijng, etc), a fishing pier, organized resort activities, a 24-hour fitness center and the on-site Spa al Mare’.

Nightly rates vary during the year but typically range from around $700 per night to more than $1,100 per night depending on the room type. If you are a Hilton Honors member you can use points for your stay – we found that starting from 90,000 points per night are needed for a free night stay at this hotel.

Click here for rates & reservations at the Reach Hotel Key West

Sunset Key Cottages Resort

Located just off Key West is the 27-acre private island oasis which is home to the Sunset Key Cottages.  This island retreat is home to just 40 individual cottages and can only be accessed via a 24-hour shuttle boat.

Amenities include a very private white sandy beach, zero entry swimming pool with two whirlpool tubs, 24-hour fitness center, extensive concierge service, tennis courts, the AAA Four Diamond Latitudes Restaurant and the on-site Spa at Sunset Key.  In addition a breakfast basket is delivered daily to each cottage.  The fourt bedroom cottages have individual plunge pools.

Nightly rates vary during the year but typically range from around $1,000 per night to more than $3,500 per night depending on the cottage type. 

Click here for rates & reservations at the Sunset Key Cottages Resort

Baker’s Cay Resort Key Largo

The Baker’s Cay Resort Key Largo is part of the Curio Collection by Hilton.  This 200-room property is located on 13-beachfront acres in the upper Florida Keys.  It is one of the most tranquil hotels on our list, perfect for a relaxing weekend getaway.     

Amenities at Baker’s Cay include a private beach with a number of water sports activities (paddleboard, snorkeling, Jet Skiing, kayakijng, etc), a boat dock, outdoor pool area, organized resort activities and a state-of-the-art fitness center. 

Nightly rates vary during the year but typically range from around $800 per night to more than $2,000 per night depending on the room type. If you are a Hilton Honors member you can use points for your stay – we found that starting from 90,000 points per night are needed for a free night stay at this hotel.

Click here for rates and reservations at the Baker’s Cay Resort Key Largo

Endless Summer

Endless Summer Florida is all about amazing places to Vacation in Florida. From world class theme parks to white sandy beaches, there is so much to see and do in our state.

Recent Posts

Amazing Florida Beaches
Amazing Florida Beaches