The KeysLuxury Hotels with Entertainment

List Of Best Luxury Hotels with Entertainment The Keys

We have created a list with the best luxury hotels with entertainment in The Keys, USA. Hope you enjoy it. We think it might be the best of its kind around

luxury hotels in The Keys
Cheeca Lodge & Spa
Resort
81801 Overseas Highway Mile Marker 82, Islamorada, FL 33036, USA

Welcome to Cheeca Lodge & Spa, a beautiful resort nestled in Islamorada, Florida, surrounded by 27 acres of stunning gardens and offering a private waterfront for your enjoyment. Whether you're looking to relax or have an adventure, our resort has something for everyone. You can play a round of golf on our charming 9-hole par 3 course, or treat yourself to some well-deserved pampering at our on-site spa. With a variety of accommodations available, we strive to create a comfortable and inviting atmosphere for all our guests. We believe that every visitor deserves a special experience, and our friendly staff is here to help you make the most of your stay. Come discover the beauty and tranquility of Cheeca Lodge & Spa, where you can unwind and connect with nature in a welcoming environment.

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Luxury Amenities:

  1. Enjoy the serenity of your own private beach, with soft sands and endless ocean views.
  2. Wake up to breathtaking ocean views, a stunning start to every morning.
  3. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  4. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
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luxury hotels in The Keys
Playa Largo Resort & Spa, Autograph Collection
Resort
97450 Overseas Highway, Key Largo, FL 33037, USA

Welcome to Playa Largo Resort & Spa, a beautiful destination where you can unwind in one of our 155 luxurious rooms, all filled with natural light and stunning views of Florida Bay. Enjoy breathtaking sunsets that paint the sky in vibrant colors every evening. We are proud to be the first new resort built in the Florida Keys in over 23 years, bringing fresh energy and modern comforts to this stunning area. Whether you're here for a family vacation, a romantic getaway, or a solo retreat, our goal is to create a welcoming and memorable experience for everyone who visits us.

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Luxury Amenities:

  1. Enjoy the serenity of your own private beach, with soft sands and endless ocean views.
  2. Wake up to breathtaking ocean views, a stunning start to every morning.
  3. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  4. Stay productive with top-notch business services available at your fingertips.
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luxury hotels in The Keys
Isla Bella Beach Resort & Spa - Florida Keys
Resort
1 Knights Key Boulevard MM47, Marathon, FL 33050, USA

Welcome to Isla Bella Beach Resort, a beautiful getaway located in Marathon. Here, you can enjoy a stunning private beach that’s perfect for relaxation and fun in the sun. We’re conveniently close to exciting attractions like Conch-Air Florida Keys Scenic Flights, just 7 km away, and the Florida Keys Aquarium Encounters, which is only 10 km from our resort. With so much to see and do nearby, you’ll have plenty of opportunities to explore and create lasting memories with your loved ones. We can’t wait to welcome you!

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Luxury Amenities:

  1. Enjoy the serenity of your own private beach, with soft sands and endless ocean views.
  2. Wake up to breathtaking ocean views, a stunning start to every morning.
  3. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  4. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
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luxury hotels in The Keys
Grassy Flats Resort & Beach Club
Hotel
58182 Overseas Hwy,Marathon FL 3305, Marathon, FL 33050, USA

Grassy Flats Resort & Beach Club is a welcoming place to stay in Marathon, just 8.6 km from the Florida Keys Aquarium Encounters. Here, you can relax by the outdoor swimming pool, enjoy delicious meals at our restaurant, and unwind with a drink at the bar. We also offer free private parking for your convenience, ensuring a stress-free experience during your visit. Whether you’re looking for adventure or relaxation, we’re here to make your stay enjoyable and comfortable.

Show more

Luxury Amenities:

  1. Enjoy the serenity of your own private beach, with soft sands and endless ocean views.
  2. Wake up to breathtaking ocean views, a stunning start to every morning.
  3. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  4. Keep active with a range of sports and activities designed for adventure and fitness.
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luxury hotels in The Keys
Oceans Edge Key West
Resort
5950 Peninsular Ave, Key West, FL 33040, USA

Experience breathtaking views of the water at Oceans Edge Key West, part of the Preferred Hotels & Resorts Collection. Enjoy a refreshing dip in one of our six swimming pools or relax at our waterfront bar and restaurant, where you can savor delicious meals and drinks. We want all our guests to feel connected, so we offer complimentary WiFi throughout the property. Your comfort and enjoyment are our top priorities!

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Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
  4. Stay productive with top-notch business services available at your fingertips.
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luxury hotels in The Keys
The Perry Hotel & Marina Key West
Resort
7001 Shrimp Rd, Key West, 33040, USA

Welcome to The Perry Hotel & Marina Key West! Nestled at Stock Island Marina, we’re just a short bridge away from the vibrant heart of Key West. Our hotel offers comfortable and welcoming accommodations that cater to everyone. Take a refreshing dip in our waterfront pool or enjoy delicious meals at our two dockside restaurants, where we proudly serve fresh, local seafood. We look forward to making your stay enjoyable and memorable!

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Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
  4. Stay productive with top-notch business services available at your fingertips.
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luxury hotels in The Keys
Santa Maria Suites Resort
Resort
1401 Simonton Street, Downtown Key West, Key West, FL 33040, USA

Just a short stroll from the beautiful Atlantic Ocean and vibrant Duval Street, our Key West hotel offers stunning all-suite accommodations designed for your comfort. We aim to create a welcoming atmosphere where everyone can relax and enjoy the unique charm of Key West, FL. Whether you're here for a romantic getaway, a family vacation, or a friends' retreat, we want to make sure you have an unforgettable experience that meets your needs. Come and discover the beauty of Key West with us!

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Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Keep active with a range of sports and activities designed for adventure and fitness.
  4. Rejuvenate at the state-of-the-art wellness facilities designed for your complete relaxation.
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luxury hotels in The Keys
H2O Suites- Adults Only
Resort
1212 Simonton Street, Downtown Key West, Key West, FL 33040, USA

Welcome to Key West H2O Suites, a peaceful retreat designed just for adults. Located just a short 200-meter walk from the vibrant Duval Street, our hotel offers a relaxing getaway. You can unwind at our beautiful rooftop pool all year round, complete with a sun terrace where you can soak up the sun. Feel free to visit our on-site bar to enjoy a refreshing drink during your stay. Each suite is equipped with a flat-screen TV and all the comforts you need to feel right at home. We can't wait to welcome you!

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Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Keep active with a range of sports and activities designed for adventure and fitness.
  4. Rejuvenate at the state-of-the-art wellness facilities designed for your complete relaxation.
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luxury hotels in The Keys
The Gardens Hotel
Hotel
526 Angela Street, Downtown Key West, Key West, FL 33040, USA

Welcome to our adult-only hotel in the beautiful Key West, Florida! Here, you can unwind and enjoy two inviting outdoor pools. We’re conveniently located just a minute’s walk from lively Duval Street, where you can explore shops, restaurants, and nightlife. If you’re interested in nature, the Key West Butterfly and Nature Conservatory is only a quick 3-minute drive away. We look forward to helping you create wonderful memories during your stay!

Show more

Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
  4. Stay productive with top-notch business services available at your fingertips.
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luxury hotels in The Keys
The Saint Hotel Key West, Autograph Collection
Hotel
417 Eaton Street, Downtown Key West, Key West, FL 33040, USA

The Saint Hotel Key West welcomed its guests on February 1, 2015, after six months of thoughtful renovations. We transformed a standard hotel into a charming boutique experience inspired by the allure of a historical bordello. Our goal was to create a welcoming space that feels both unique and comfortable for everyone who walks through our doors. The updates include stylish decor and inviting communal areas designed for relaxation and connection. We are dedicated to making your stay enjoyable and memorable!

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Luxury Amenities:

  1. Stay productive with top-notch business services available at your fingertips.
  2. Keep active with a range of sports and activities designed for adventure and fitness.
  3. Savor gourmet dishes at an exquisite restaurant without ever leaving the hotel.
  4. Delight in premium entertainment options that ensure fun-filled evenings throughout your stay.
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luxury hotels in The Keys
Ocean Key Resort & Spa, a Noble House Resort
Resort
Zero Duval, Downtown Key West, Key West, FL 33040, USA

Experience the beauty of the Gulf of Mexico at our inviting Key West resort and spa. Enjoy relaxing moments by our outdoor pool, where you can take in stunning views of the water. We want to make your stay comfortable, so we offer free WiFi for all our guests. If you’re looking to unwind, visit SpaTerre on-site, where our skilled therapists offer a variety of massage treatments designed just for you. Your comfort and enjoyment are our top priorities!

Show more

Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Stay productive with top-notch business services available at your fingertips.
  4. Keep active with a range of sports and activities designed for adventure and fitness.
Show more
luxury hotels in The Keys
JW Marriott Marco Island Beach Resort
Resort
400 South Collier Boulevard, Marco Island, FL 34145, USA

Welcome to our beautiful beachfront resort on Marco Island, Florida! Here, you can relax by one of our three outdoor pools or enjoy a round of golf at one of our two private 18-hole courses. We offer a variety of dining options with ten different restaurants to suit all tastes. Plus, there are plenty of activities available for everyone, including volleyball and more. Whether you're looking to unwind or stay active, we have something for everyone to enjoy during your stay!

Show more

Luxury Amenities:

  1. Enjoy the serenity of your own private beach, with soft sands and endless ocean views.
  2. Wake up to breathtaking ocean views, a stunning start to every morning.
  3. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  4. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
Show more
luxury hotels in The Keys
Naples Bay Resort and Marina
Resort
1500 5th Avenue South, Naples, FL 34102, USA

Welcome to Naples Bay Resort and Marina, a place where you can relax and enjoy the beautiful surroundings. Our resort offers a lovely marina and a spacious 5,000-square-foot outdoor pool—perfect for soaking up the sun or enjoying a refreshing swim. Each of our comfortable rooms is equipped with free WiFi, so you can stay connected during your visit. Plus, we’re conveniently located just under a mile from the scenic Naples Pier, where you can take in stunning views and explore local attractions. Whether you're here for a family vacation, a romantic getaway, or a solo retreat, we strive to make your stay enjoyable and memorable. We look forward to welcoming you!

Show more

Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
  4. Stay productive with top-notch business services available at your fingertips.
Show more

Most booked hotels with Entertainment in The Keys

luxury hotels in The Keys
5950 Peninsular Ave, Key West, FL 33040, United States of America
8.6
1243 reviews
From $884
luxury hotels in The Keys
81801 Overseas Highway Mile Marker 82, Islamorada, FL 33036, United States of America
8.6
1061 reviews
From $865
luxury hotels in The Keys
1 Knights Key Boulevard MM47, Marathon, FL 33050, United States of America
8.7
637 reviews
From $2572

Budget hotels with Entertainment in The Keys

luxury hotels in The Keys
1500 5th Avenue South, Naples, FL 34102, United States of America
9.6
7 reviews
From $369
luxury hotels in The Keys
417 Eaton Street, Downtown Key West, Key West, FL 33040, United States
8.2
41 reviews
From $723
luxury hotels in The Keys
1401 Simonton Street, Downtown Key West, Key West, FL 33040, United States of America
9.3
634 reviews
From $808

Compare the Top Luxury Hotels with Entertainment in The Keys – Addresses, Prices, Stars, Rating, and Review Count

Hotel Name Address Price ($) Star Rating Review Count Book
Cheeca Lodge & Spa 81801 Overseas Highway Mile Marker 82, Islamorada, FL 33036, USA 865 5 8.6 1061
Playa Largo Resort & Spa, Autograph Collection 97450 Overseas Highway, Key Largo, FL 33037, USA 989 5 8.6 344
Isla Bella Beach Resort & Spa - Florida Keys 1 Knights Key Boulevard MM47, Marathon, FL 33050, USA 2572 5 8.7 637
Grassy Flats Resort & Beach Club 58182 Overseas Hwy,Marathon FL 3305, Marathon, FL 33050, USA 2344 3 9 541
Oceans Edge Key West 5950 Peninsular Ave, Key West, FL 33040, USA 884 4 8.6 1243
The Perry Hotel & Marina Key West 7001 Shrimp Rd, Key West, 33040, USA 883 4 8.9 289
Santa Maria Suites Resort 1401 Simonton Street, Downtown Key West, Key West, FL 33040, USA 808 4 9.3 634
H2O Suites- Adults Only 1212 Simonton Street, Downtown Key West, Key West, FL 33040, USA 1688 4 9.3 533
The Gardens Hotel 526 Angela Street, Downtown Key West, Key West, FL 33040, USA 1074 4 9.6 146
The Saint Hotel Key West, Autograph Collection 417 Eaton Street, Downtown Key West, Key West, FL 33040, USA 723 4 8.2 41
Ocean Key Resort & Spa, a Noble House Resort Zero Duval, Downtown Key West, Key West, FL 33040, USA 2138 4 8.4 141
JW Marriott Marco Island Beach Resort 400 South Collier Boulevard, Marco Island, FL 34145, USA 1356 4 8.6 397
Naples Bay Resort and Marina 1500 5th Avenue South, Naples, FL 34102, USA 369 4 9.6 7

Note: The prices for each hotels in The Keys do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here>) to get the latest prices.

Frequently Asked Questions

These 3 star hotels received great reviews from other travelers:

Some of the best hotels with entertainment options in The Keys include The Margaritaville Key West Resort & Marina, the Ocean Key Resort & Spa, and Hawks Cay Resort. These properties offer live music, poolside activities, and themed events to keep guests entertained during their stay.

Yes, several family-friendly hotels in The Keys provide entertainment for all ages. Resorts like the Hawks Cay Resort offer kids' clubs, water sports, and family movie nights, ensuring that everyone has a great time.

Hotels in The Keys typically offer a variety of entertainment options such as live music, pool parties, beachfront activities, and outdoor movie nights. Many resorts also host special events like themed dinners and happy hours.

While all-inclusive resorts are rare in The Keys, some properties like Club Med in nearby areas offer packages that include meals and activities. Always check directly with the hotel to see what entertainment is included in your stay.

Absolutely! Hotels like the Sunset Key Cottages and The Marker Waterfront Resort feature stunning waterfront views along with live entertainment options. Enjoy a night of music while soaking in the beauty of the ocean.

For a romantic getaway, consider hotels like the Ocean Key Resort & Spa or Casa Marina. Both provide intimate settings with live music, sunset celebrations, and couples’ activities designed to enhance your experience.

Yes, many hotels in The Keys regularly host events and festivals, especially during peak tourist seasons. Check out places like the Key West Holiday Fest or the Music Festival at the Casa Marina for exciting entertainment options.

If you're looking for nightlife, the Margaritaville Key West Resort & Marina and the Bourbon Street Pub are among the top spots. They offer lively bars and entertainment options that cater to night owls.

3-Day The Keys Itinerary If You're Staying at a Luxury Hotel

Day 1:

  • Morning: Start your day with a leisurely breakfast at Breakfast at Tiffany's, known for its delightful omelettes and fresh coffee.
  • Afternoon: Explore the Ernest Hemingway Home and Museum here, where you can wander the beautiful gardens and learn about the author's fascinating life.
  • Evening: Dine at Maloney's Lawless for some delicious seafood and enjoy sunset views over the water.

Day 2:

  • Morning: Visit the iconic Southernmost Point Buoy here to snap a picture and relish the start of your day.
  • Afternoon: Delight in a cultural experience at the Key West Art & Historical Society here, showcasing local art and history.
  • Evening: Enjoy an exquisite dinner at Prime Steakhouse, known for its elegant atmosphere and prime cuts.

Day 3:

  • Morning: Start your day by relaxing at the pristine Smathers Beach here, where you can soak up the sun or partake in water sports.
  • Afternoon: Visit the Mallory Square here for some shopping and street performances, immersing yourself in local culture.
  • Evening: Conclude your trip with a cruise aboard a sunset sail here, enjoying breathtaking views of the horizon.

🛏️ Hotels perfect for this itinerary: Havana Cabana at Key West, The Reach Key West, Curio Collection by Hilton, Casa Marina Key West, A Waldorf Astoria Resort

Where to Stay in The Keys: Best Areas by Traveler Type

Choosing the right area to stay in The Keys is essential for maximizing your vacation experience, as each neighborhood offers unique charms tailored to different traveler needs. From romantic hideaways to family-friendly spots, The Keys boasts a diverse range of neighborhoods. This guide will help you navigate through these options and find your perfect fit for an unforgettable stay.

👫 Where to Stay in The Keys for Couples

Best Areas: Key West, Islamorada

Why it’s perfect: Intimate settings perfect for romance and relaxation. Stunning sunset views and beachfront access. A variety of dining and nightlife options that cater to couples.

Top Hotels: Ocean Key Resort & Spa, Cheeca Lodge & Spa

Top Features: Romantic views, Private beach access, Cozy fire pits


👨‍👩‍👧 Where to Stay in The Keys with Family

Best Areas: Marathon, Key Largo

Why it’s perfect: Family-friendly attractions and activities nearby. Spacious accommodations suitable for families. Easy access to nature parks and snorkeling spots.

Top Hotels: The Hammocks at Marathon, Holiday Inn Key Largo

Top Features: Kid-friendly pools, Adventure activities, Game rooms


🧳 Where to Stay in The Keys for Solo Travelers

Best Areas: Key West, Big Pine Key

Why it’s perfect: Vibrant social scene and opportunities to meet fellow travelers. Cafés and bars offering local vibes. Variety of solo-friendly activities and tours.

Top Hotels: Hostel on the Beach, Blue Marlin Motel

Top Features: Social gatherings, Affordable rates, Proximity to attractions


👵👴 Where to Stay in The Keys for Seniors

Best Areas: Key Largo, Islamorada

Why it’s perfect: Tranquil environment with accessible amenities. Relaxed pace and scenic views for leisurely exploration. Cultural experiences and guided tours available.

Top Hotels: Bayside Inn Key Largo, Islander Waterside Resort

Top Features: Accessible facilities, Calm atmosphere, Engaging local tours


💸 Where to Stay in The Keys on a Budget

Best Areas: Key West, Marathon

Why it’s perfect: Affordable accommodations without compromising quality. Free or low-cost activities available nearby. Local eateries and attractions suited for budget-conscious travelers.

Top Hotels: Fairfield Inn & Suites by Marriott Key West, Kingsail Resort

Top Features: Budget-friendly dining options, Access to public beaches, Discounted attraction passes


💎 Where to Stay in The Keys for Luxury

Best Areas: Key West, Islamorada

Why it’s perfect: High-end amenities and exceptional service. Exclusive experiences tailored for luxury travelers. Stunning beachfront properties with premium views.

Top Hotels: Grove Isle Hotel & Spa, The Reach Key West, Curio Collection by Hilton

Top Features: Spa and wellness centers, Gourmet dining options, Private pools


Where to Stay in The Keys - Quick Guide

Traveler Type Best Areas Top Features
Couples Key West, Islamorada Romantic views, Private beach access, Cozy fire pits
Family Marathon, Key Largo Kid-friendly pools, Adventure activities, Game rooms
Solo Key West, Big Pine Key Social gatherings, Affordable rates, Proximity to attractions
Seniors Key Largo, Islamorada Accessible facilities, Calm atmosphere, Engaging local tours
Budget Key West, Marathon Budget-friendly dining options, Access to public beaches, Discounted attraction passes
Luxury Key West, Islamorada Spa and wellness centers, Gourmet dining options, Private pools