Heading to the Florida Keys on your next vacation? Any one of these resorts is sure to help create the ideal getaway. From family-friendly activity-packed resort properties to romantic bungalows, we’ve put together the ultimate list below.
Sunset Key Cottages, Key West
Sunset Key Cottages is a popular beach resort in Key West with just a small collection of rooms, which caters to upscale travelers, hosting luxurious, beach-chic cottages and sophisticated amenities. Located on Sunset Key, a residential island just 500 yards off Key West, you’ll find a magnificent palm-tree-lined beach and clear waters, along with a beautiful pool and spa. This idyllic, exclusive property can be reached via boat ferry service from Key West 24 hours a day and boasts an authentic island experience across 27 lush acres. Accommodation options include private homes as well as two, three and four-bedroom cottages, all capturing the casual Key West lifestyle, including tranquility and charm with Victorian-style tin rooms and pastel-hued wood finishes.
Key Amenities:
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Private island with 24-hour boat ferry service from Key West
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Homes, two, three and four-bedroom cottages
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Pool, spa, private beach and signature restaurant on-site
Tranquility Bay Beach House Resort, Marathon
One of the best couples resorts in the U.S., Tranquility Bay Beach House Resort sits across 12 waterfront acres on Marathon Key. This property features luxurious and tropical Victorian-style homes divided into multi-story two and three-bedroom suites with kitchens and stunning water views. Each beach house includes a separate dining area as well as a living room. You’ll love the French doors on both levels, which lead to expansive porches with magnificent unobstructed water views of the Gulf of Mexico. You’ll also have access to a private beach.
Key Amenities:
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Beach houses with suites, full kitchens and large porches
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Private beach and waterfront views
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On-site spa and restaurant
The Reach Key West, Curio Collection by Hilton, Key West
The Reach offers relaxed sophistication with a quiet getaway, away from the chaos and crowds of Key West, in a beachfront location. This full-service, luxury resort offers sleek rooms with modern amenities as well as shared access to its sister Casa Marina resort nearby, including a spa and tennis. Savor delectable cuisine amid sea breezes on the open-air wood deck of the Four Marlins Restaurant. Rooms with various layouts contain high-end furnishings, including especially comfy beds, along with iPod docks, espresso machines, and wet bars – all along with a private stretch of white sandy beach and a pier for fishing. You can spend your days basking in the sun at the beachfront pool featuring cabanas and a poolside concierge.
Key Amenities:
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Nautical-themed rooms and suites with private balcony
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Private natural sand beach and pier for fishing
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Shared access to sister resort Casa Marina for spa and tennis
Cheeca Lodge & Spa, Islamorada
The Cheeca Lodge & Spa is a time-honored resort as one of Islamorada’s original luxury properties, dating back to 1946. One of the largest resorts in the Keys, it sits on 27 acres and is also big when it comes to amenities. You’ll find lots of luxurious touches, including soaking tubs that fill with a stream from the ceiling as well as the chance to soak up fabulous views from the glass and floor-to-ceiling showers. There are multiple oceanfront dining establishments on site, including a sushi bar, as well as one adults-only and two family pools. There is also a 1,200-foot private beach, access to bikes, kayaks, fishing rods, a walking trail and an educational program for kids.
Key Amenities:
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Casitas, rooms and suites with dog-friendly options
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Private beach with boat slips
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Kids camp and three pools, including adults-only pool
81801 Overseas Hwy, Islamorada, FL 33036, USA— +1 305-664-4651
Southernmost on the Beach, Key West
A favorite with families in the Keys, Southernmost on the Beach offers polished rooms with soothing, beach-inspired décor – most have balconies, and some feature corner, wrap-around balconies with jaw-dropping ocean views. Enjoy lounging in a hammock, strung between the palm trees or reading a book in an Adirondack chair that overlooks the water. You’ll also love the beautiful beach, private sunbathing pier and long pool. The location on the quiet end of Duval also means you won’t have to deal with the hustle and bustle of downtown unless you want to – it can be reached within about a 20-minute walk. The beach is right across the street, along with a restaurant, and you can also grab a drink and a snack from the onsite pool bar.
Key Amenities:
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Rooms, suites and guesthouses at nearby property
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Beach, private sunbathing pier and long pool
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Convenient Old Town Key West location
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West features stylish rooms that are light and sophisticated with an island feel, featuring sleek hardwood or tiled floors along with sheer curtains and neutral tones. The beautiful grounds are filled with lush foliage and palm trees, while the property also boasts a hard-to-find amenity in Key West, a 1,100-foot-long swimmable beach. As of October 2023, the renovated resort will feature a new, tropical contemporary style, transformed guestrooms, an airy lobby lined with windows framing the beach, two activity piers, enhanced food and beverage venues, and more.
Key Amenities:
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Large, private swimmable beach
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On-site spa and two heated pools
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Fire pits and live entertainment
*Casa Marina is temporarily closed for renovations until October 2023.
Hawks Cay Resort, Duck Key
As you step into Hawks Cay Resort, you’ll feel as if you’re entering a small village with its huge size and a long list of amenities, including having its own 85-slip marina. Many of the guests arrive at this top-rated family beach resort in Florida by boat, as it’s located on Duck Key. Popular with families and for family reunions, with a multitude of activities, including a dolphin experience, miniature golf, and a kids’ club, as well as its multi-bedroom villas and a small beach that sits at the edge of calm waters. The diverse ecosystem offers the chance for renowned fishing, and also brings the beloved Atlantic bottlenose dolphin right along the shore.
Key Amenities:
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Multi-bedroom villas, rooms and suites
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Large resort village with dining, stores and marina
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Dolphin experience, miniature golf and kids club
Ocean Key Resort & Spa, Key West
With an address like Zero Duval Street, you know that Ocean Key Resort & Spa has got it all. Situated adjacent to the historic Mallory Square with its iconic Key West attractions, this alluring resort boasts stunning waterfront views overlooking the Gulf of Mexico and the Sunset Pier with its famous daily Sunset Celebration. Don’t miss dining at its highly acclaimed Hot Tin Roof Restaurant, then relax your weary muscles in the world-class SpaTerre. Celebrating something special? Stay in a Deluxe Oceanfront Room for ocean views, a king-size bed, spa tub, and an in-room mini-bar. All guests can enjoy the VIP Service and great music at the poolside bar LIQUID and can organize sunset sails or fishing excursions.
Key Amenities:
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Location adjacent to Mallory Square and Sunset Pier
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VIP service at exclusive LIQUID poolside bar
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Private balconies with oceanfront or Duval Street views
Hyatt Centric Key West Resort & Spa, Key West
Hyatt Centric Key West Resort & Spa offers its own manmade beach and is one of the few properties where you can soak up the sun and the sand while also being just a short stroll away from the streets of Old Town. You can enjoy an extensive array of water sports, too, as well as fitness options and excellent on-site restaurants. Rooms feature an island flair, balconies overlooking the gulf, and walk-in showers with rain showerheads. Guests are also pampered with lovely touches like fluffy robes and heavenly down comforters.
Key Amenities:
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Dog-friendly rooms and suites with furnished balconies
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On-site pool and spa
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Private manmade beach with docks
Reefhouse Resort & Marina, Key Largo
Reefhouse Resort & Marina can be found in northern Key Largo, just a short drive from the John Pennekamp Coral Reef State Park, world-renowned for its outstanding snorkeling and diving opportunities. It’s also close to many shops and restaurants. Right on-site, you’ll find a diver’s center, spa, and a small private beach. Unwind with cocktails, live music, and panoramic views at Breezer’s Tiki Bar, or visit Gus’ Grille, one of the best Key Largo restaurants on the water. For the best experience, be sure to book a room with an ocean view for taking in the awe-inspiring Key Largo sunsets.
Key Amenities:
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On-site diver’s center and marina
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Private beach access
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Waterfront spa and pool
103800 Overseas Highway Mm 103.8, Key Largo, FL 33037, USA— +1 305-453-0000
Pier House Resort and Spa, Key West
The Pier House Resort and Spa sits on a tranquil stretch of sand at the foot of Duval, offering an ideal quiet setting while still being close to all of the action Key West is known for. Enjoy cozy, colorful rooms with a pool, garden or ocean view – or choose one of the high-end suites that extend right over the water. The courtyard is dotted with soaring coconut palms and hibiscus blossoms. It stands out from the competition with its outstanding amenities that include an onsite spa, pool, restaurant, and bar – the oldest in Key West, as well as proximity to Sunset Pier for watching the sun go down in style.
Key Amenities:
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Oldest bar in Key West
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Private white sand beach
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Full-service spa
Little Palm Island Resort & Spa, Little Torch Key
Known as the best of the best when it comes to Florida Key Resorts, this Gilligan’s Island-like resort boasts luxury accommodation along with extraordinary service – all accessed only via boat or seaplane. You’ll enjoy spacious rooms under a thatched roof, as well as spectacular views of the water and bamboo-enclosed outdoor showers. The property is also known for its number of thoughtful touches, including having your name in woodblocks above the door. This piece of paradise is home to a private marina as well as some of Florida’s most gorgeous stretches of sand.
Key Amenities:
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Adults-only private island resort
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Thatched roof bungalows and bamboo outdoor showers
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Private marina, pool and beach
28500 Overseas Hwy, Little Torch Key, FL 33042, USA— +1 305-684-8341
Parrot Key Hotel & Villas, Key West
Located along the Gulf of Mexico, just minutes from Historic Old Town, Parrot Key Hotel & Villas offers the feel of an old-fashioned beach community – complete with rocking-chair porches and picket fences. Mangroves line its manmade beach at the edge of Florida Bay, while room décor features cheery pastels with beach cottage chic. Set across five acres of beautifully landscaped grounds, this waterfront hotel boasts multiple secluded swimming pools, each surrounded by lush gardens as well as white-sand sunbathing terraces, glorious sunsets, and lots of water sports right onsite.
Key Amenities:
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Private manmade beach and Smathers Beach Club access
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Multiple secluded swimming pools
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Discounts on local area activities
2801 N Roosevelt Blvd, Key West, FL 33040, USA— +1 888-665-6368
Havana Cabana Resort, Key West
Havana Cabana Resort embodies Cuba’s vibrant art and culture with its tropical design and decor, featuring classic cars out front. You can enjoy ice-cold mojitos and great music poolside, then fill up with classic Cuban fare at the hotel’s Floridita Food Truck. One of its highlights is being home to the largest pool in Key West, where you can escape from your everyday stress and soak in the sunshine while enjoying fun features like cabanas, hammocks, and lounge chairs. The bright and airy rooms feature boutique amenities, with the Gulf View Rooms one of the most romantic overlooking the sparkling ocean.
Key Amenities:
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Largest pool in Key West with DJ on weekends
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Inspired by Cuba with tropical design and Cuban fare
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On-site scooter and bicycle rentals
3420 N Roosevelt Blvd, Key West, FL 33040, USA— +1 305-294-5541
Chesapeake Beach Resort, Islamorada
Chesapeake Beach Resort is set along the beach and blends a retro look with modern conveniences. Most rooms are lined along the shore, encircling a lagoon, while others overlook a tennis court. You’ll find high-tech features like flat-screen TVs along with coral stone and dark wood accents. Enjoy a tropical atmosphere with a lush private lagoon, exotic birds, flowering hibiscus, swaying palms and endless ocean views. Enjoy swimming in one of the outdoor heated pools or soak in the spa, both along the waterfront. Activity options include unlimited use of non-motorized watersports right on-site, including kayaking, pedal boating, biking and sailing.
Key Amenities:
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Two outdoor heated pools with ocean views
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Balconies with ocean or island views on each room
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Kayaking, pedal boating, biking and sailing onsite
83409 Overseas Hwy, Islamorada, FL 33036, USA— +1 305-664-4662
Ocean's Edge Resort & Marina, Key West
Get away from it all at Ocean’s Edge Resort & Marina, a secluded getaway set on the water with 20 acres of serene Florida landscapes dotted with palm trees. In addition to boasting a 165-flip full-service marina, other on-site amenities include six pools, a poolside bar, and waterfront dining serving up fresh catches. If you want to explore the city, you’re just a short ride away, while a variety of water activities are at your fingertips, including scuba diving, kayaking, paddle boarding, and boat charters.
Key Amenities:
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Full-service marina
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Six pools and poolside bar
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Shuttle to Old Town Key West
5950 Peninsular Ave, Key West, FL 33040, USA— +1 877-935-0862
Postcard Inn Beach Resort & Marina at Holiday Isle, Islamorada
Postcard Inn Beach Resort & Marina, Holiday Isle offers a “boathouse chic” style, including faux-wood-tiled floors, white wood accents and comfy daybeds. The stenciled quotes from ocean lovers to ocean lovers are an especially lovely touch. For those that want to stay busy, you’ll find a multitude of things to do, from diving and snorkeling to fishing charters and water-sport rentals – as well as the famed “Holiday Isle Tiki Bar.”
Key Amenities:
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Access to amenities at three sister resorts
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Walk-in beach and marina
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Diving, snorkeling and fishing charters available
84001 Overseas Hwy, Islamorada, FL 33036, USA— +1 817-541-8775
Isla Bella Beach Resort, Marathon
Isla Bella Beach Resort & Spa is a tropical getaway where you can get away from it all. Along with pristine sandy beaches, it features a marina where you can sign up for harbor cruises and kayaking or snorkeling trips, a world-class Polynesian-inspired restaurant, and a 4,000-square-foot spa with a selection of services. Take leisurely strolls along the private shoreline or cool off with a dip in one of the multiple pools, then retreat to your oceanfront room or suite. Every room in this hotel has its own outdoor living area where you can take in the incredible views.
Key Amenities:
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One mile of waterfront
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5 oceanfront pools and a sandy beach
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Multiple dining options
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A marina with water sports
1 Knights Key Blvd, Marathon, FL 33050, USA— +1 305-481-9451
Kona Kai Resort, Key Largo
The vibrantly colored Kona Kai Resort is small and unpretentious, set across two acres as an adult hideaway that offers one of the most picturesque spots to stay in the Keys. Each of its intimate cottages boasts furnishings that add to the tropical feel, simple but thoughtful, with touches like ceramic tile floors and rattan footstool. The spacious studio, one- and two-bedroom suites come complete with full kitchens, original art and abundant natural light. Enjoy the outdoors by hanging out in a hammock or lounge chair, soaking in the hot tub, and taking in beautiful sunsets from the deck. The property is arranged around a mosaic-covered pool where you can help yourself to complimentary fruit and bottled water.
Key Amenities:
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Adults-only resort
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Cottages, studios, one-bedroom and two-bedroom suites with full kitchens
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On-site botanic garden, art gallery and pool
97802 Overseas Hwy, Key Largo, FL 33037, USA— +1 305-852-7200
Lime Tree Bay Resort, Layton
Lime Tree Bay Resort offers a more affordable seaside oasis as one of the best mid-range resorts in the Florida Keys, set across palm-shaded sandy shores. You’ll find lots of options for relaxation as well as adventure, including hammocks and a hot tub, perfect for soothing sore muscles after a long day at play. You can also enjoy kayaking on-site, cooking up meals on the barbecue grills, and swimming in one of the outdoor pools. An array of accommodation options await, including elegant rooms, most of which offer a patio or balcony with sea views. Suites feature kitchens or kitchenettes too.
Key Amenities:
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Rooms and suites with kitchens or kitchenettes
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Free continental breakfast
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Multiple pools and unlimited use of kayaks, bikes and paddleboarding
