Florida Keys Florida Luxury Hotels with Entertainment

List Of Best Luxury Hotels with Entertainment Florida Keys

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

luxury hotels in Florida 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!

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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 Florida 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!

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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. 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.
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luxury hotels in Florida 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 Florida 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 Florida 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 Florida 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 Florida 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!

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.
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luxury hotels in Florida 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!

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 Florida 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.
Show more
luxury hotels in Florida 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 Florida 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!

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
luxury hotels in Florida 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

Most booked hotels with Entertainment in Florida Keys

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

Budget hotels with Entertainment in Florida Keys

luxury hotels in Florida Keys
417 Eaton Street, Downtown Key West, Key West, FL 33040, United States
8.2
41 reviews
From $723
luxury hotels in Florida Keys
1401 Simonton Street, Downtown Key West, Key West, FL 33040, United States of America
9.3
634 reviews
From $808
luxury hotels in Florida Keys
81801 Overseas Highway Mile Marker 82, Islamorada, FL 33036, United States of America
8.6
1061 reviews
From $865

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

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

Note: The prices for each hotels in Florida 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 Florida Keys include the Casa Marina Key West, which offers live music, and the Hawks Cay Resort, known for its family-friendly activities and water sports. Visitors can enjoy vibrant nightlife, themed events, and various recreational activities.

While all-inclusive resorts are less common in the Florida Keys, some hotels like the Club Med Sandpiper Bay offer comprehensive packages that include dining and entertainment options. Be sure to check specific offerings at each location for planned activities and shows.

Hotels in the Florida Keys typically offer a variety of entertainment options, including live music, beach bonfires, water sports, and organized excursions. Many resorts also host themed nights or poolside games to keep guests engaged.

For family-friendly options, consider staying at the Isla Bella Beach Resort, which features a kids' club and various family activities, or the Hawks Cay Resort, where children can enjoy a pirate-themed adventure camp. Both hotels cater to families seeking fun and entertainment.

Yes, many hotels in the Florida Keys, particularly in Key West, feature live music events regularly. Venues like the Ocean Key Resort & Spa often showcase local talent for an enjoyable evening experience right at your hotel.

Absolutely! Resorts like the Margaritaville Key West Resort & Marina offer nightlife activities, including bars, live music, and themed parties. The lively atmosphere is perfect for those looking to unwind after a day of exploration.

When choosing a hotel with entertainment in the Florida Keys, look for amenities such as live music venues, organized activities, water sports facilities, and multiple dining options. These features enhance your stay and provide plenty of entertainment opportunities.

The Hilton Key Largo Resort boasts a stunning pool area with live music by the poolside, while the Sundowners Beach Bar at the Holiday Inn Key Largo often hosts fun events. Both places make for great spots to relax and enjoy entertainment.

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

Day 1:

  • Morning: Start your day with a sumptuous breakfast at Colombian Coffee House, known for its delicious coffee and pastries. Take a stroll around the charming streets of Old Town Key West, admiring the historic architecture.
  • Afternoon: Visit the iconic Ernest Hemingway Home and Museum to learn about the author's fascinating life. Then head to the Duval Street for some shopping and vibrant local culture.
  • Evening: Dine at Sunset Grille while enjoying panoramic views of the sunset. After dinner, enjoy live music at Sloppy Joe's Bar, a legendary Key West hotspot.

Day 2:

  • Morning: Have breakfast at Breakfast at Tiffany's, famous for its comforting brunch options. Spend some time relaxing on South Beach, where you can soak up the sun and enjoy the lively atmosphere.
  • Afternoon: Explore the underwater world by taking a snorkeling tour at Florida Keys National Marine Sanctuary. This is a perfect spot to witness vibrant marine life and coral reefs.
  • Evening: Savor fresh seafood at The Lobster Shack, offering a laid-back dining experience. Later, attend a performance at the Key West Theater for a memorable evening of entertainment.

Day 3:

  • Morning: Enjoy a leisurely breakfast at Blue Heaven, renowned for its outdoor seating and roosters roaming freely. Afterward, visit the Key West Botanical Garden to experience the lush tropical flora.
  • Afternoon: Spend your afternoon at the Mallory Square, where you can enjoy various street performances and art exhibits. Don’t miss out on the fantastic local shops in the area.
  • Evening: Indulge in a farewell dinner at Agricole, featuring exquisite farm-to-table dishes. Conclude your trip with a sunset sailboat cruise through the stunning waters of Key West.

🛏️ Hotels perfect for this itinerary: The Southernmost Inn, Ocean Key Resort & Spa, Casa Marina Key West

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

Choosing the right area to stay in the Florida Keys can significantly enhance your vacation experience, depending on your travel needs. With its diverse neighborhoods catering to various interests—romantic escapes, family adventures, solo explorations, and luxury indulgences—this guide will help you find the best fit for your unique travel style. Whether you're looking for peaceful beaches or exciting nightlife, there's something for everyone in this tropical paradise.

👫 Where to Stay in Florida Keys for Couples

Best Areas: Key West, Islamorada

Why it’s perfect: Intimate dining options and vibrant nightlife create a romantic atmosphere. Scenic sunsets and waterfront views provide charming backdrops for couples. Quaint shops and art galleries offer unique experiences to explore together.

Top Hotels: The Southernmost Beach Resort, Islander Watersports Resort, Cheeca Lodge & Spa

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


👨‍👩‍👧 Where to Stay in Florida Keys with Family

Best Areas: Marathon, Key Largo

Why it’s perfect: Family-friendly attractions like water parks and nature reserves are nearby. Wide range of accommodations that cater to families with kids. Child-friendly activities and safe environments enhance family bonding.

Top Hotels: Hawks Cay Resort, Holiday Inn Express & Suites Key Largo, Tranquility Bay Beachfront Hotel and Resort

Top Features: Spacious suites, Pools and recreational activities, Easy access to family-friendly excursions


🧳 Where to Stay in Florida Keys for Solo Travelers

Best Areas: Key West, Big Pine Key

Why it’s perfect: Vibrant social scenes make it easy to meet other travelers. Plenty of solo-friendly activities, from diving to exploring local cafes. Safe environments allow for comfortable exploration at one's own pace.

Top Hotels: The Marker Waterfront Resort, Ocean Key Resort & Spa, Lighthouse Court Hotel

Top Features: Communal spaces, Proximity to popular bars and restaurants, Unique local experiences


👵👴 Where to Stay in Florida Keys for Seniors

Best Areas: Key Largo, Marathon

Why it’s perfect: Quiet surroundings ensure a relaxing getaway. Accessible facilities and services cater to older adults. A slower pace allows for leisurely exploration and enjoyment.

Top Hotels: Baker's Cay Resort Key Largo, Glunz Ocean Beach Hotel & Resort, Courtyard by Marriott Marathon Florida Keys

Top Features: Easy beach access, Wellness programs, Calm ambiance


💸 Where to Stay in Florida Keys on a Budget

Best Areas: Key Largo, Islamorada

Why it’s perfect: Affordable dining options and free public beaches. Variety of budget-friendly accommodations available. Local markets and shops offer great deals on food and souvenirs.

Top Hotels: Key Largo Bay Marriott Beach Resort, Amy Slate's Amoray Dive Resort, Postcard Inn Beach Resort & Marina

Top Features: Cost-effective rates, Free parking options, Access to public transportation


💎 Where to Stay in Florida Keys for Luxury

Best Areas: Key West, Islamorada

Why it’s perfect: High-end amenities and exceptional service enhance the luxurious experience. Stunning coastal views and private beaches for relaxation. Fine dining experiences and exclusive activities cater to discerning travelers.

Top Hotels: Little Palm Island Resort & Spa, Ocean Edge Resort & Club, Rosewood Miramar Beach

Top Features: Private villas, Gourmet dining, Spa services


Where to Stay in Florida 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 Spacious suites, Pools and recreational activities, Easy access to family-friendly excursions
Solo Key West, Big Pine Key Communal spaces, Proximity to popular bars and restaurants, Unique local experiences
Seniors Key Largo, Marathon Easy beach access, Wellness programs, Calm ambiance
Budget Key Largo, Islamorada Cost-effective rates, Free parking options, Access to public transportation
Luxury Key West, Islamorada Private villas, Gourmet dining, Spa services