From five-star tropical resorts to dedicated dive hotels, the Florida Keys are covered with unique places to stay – many of them with waterfront views, all surrounded by the relaxing tropical landscape of the islands. While we can’t possibly cover all the hotels and resorts the Florida Keys have to offer, we’ll highlight a couple of the highly acclaimed resorts & hotels that best capture the unique ambience of the Keys.

This page is organized by Island, then by accommodation type: Resort: Comprehensive luxury accommodations that often sprawl across entire islands and offer everything from concierge services to wedding planning. Resorts are preferred by business travelers, honeymooners, and those treating themselves to a truly indulgent vacation.

Hotels & Guest Houses: Dive resorts, and smaller, mom-and-pop style hotels that offer amenities ranging from basic rooms to multi-room suites with kitchens, screened porches, and extras such as pools, cooked-to-order breakfasts, and manmade beaches for guests. These are lower in price, have high rates of return from past visitors, and are a good choice for divers, fishermen, families, and those desiring personal service in an intimate setting.

Photo of Holiday Isle Beach

KEY WEST

Resorts:  

Pier House Resort & Caribbean Spa – One Duval Street

Reserve one of the Pier House’s 126 guest rooms or 16 suites for opulent beachfront living in Old Town Key West. Most rooms have private patios or balconies with views of the ocean, the gardens, or the pool. The Caribbean Spa offers a selection of indulgent full-body and facial treatments, a sauna and steam room, and a health club. Restaurants include One Duval, the Beach Bar & Grille, Havana Docks Sunset Deck, and the Chart Room Bar for drinks. The Pier House has a private white sand beach with a secluded stretch for topless sunbathing, a hair and nail salon, a garden hot tub, a pool and a whirlpool, and nightly live entertainment. Tours, water sports, and fishing and diving excursions can be arranged through the hotel.

Hilton Key West Resort & Marina – 245 Front Street

Hilton has long been known for pampering its guests, and the newly built Key West installation is no exception. Located in a more peaceful neighborhood a short jaunt from Duval Street, the Hilton’s 178 Victorian-style guest rooms feature mini-bars and private balconies along the Gulf. Guests gain access to the white sand beaches of the exclusive Sunset Key Resort, located offshore and reached by a shuttle boat. The Hilton operates a full-service marina, a fine cuisine restaurant, a rooftop cocktail lounge, a poolside bar, and a Sunset Pier that celebrates nightly.

Ocean Key Resort – Zero Duval Street

The ocean- and island-view suites at Ocean Key feature high ceilings and private balconies overlooking the resort’s premiere location between Mallory Square and Key West Harbor. Stroll along the Sunset Pier, take a dip in the pool, and sit awhile at the oceanfront grill & bar. The Ocean Key has all the amenities you’d expect in a luxury resort, such as concierge, laundry, and room services, plus there’s a beer garden, in-room data ports, a dive shop and a convenience shop. Of course, there’s also parasailing, windsurfing, jet skiing, diving, snorkeling, boating, fishing, and bicycle rentals. The on-site spa and event facilities make this a great spot for a wedding, too.

Hotels & Guest Houses:

The Mermaid & the Alligator – 729 Truman Avenue

Located in the center of Old Town, this is one of Key West’s institutions and the recipient of many prestigious awards and recognitions. Each room in the Victorian mansion is individually decorated and range from a “treetop suite” to “the garden room,” complete with French doors. Outside, guests can cool off in the plunge pool, sunbathe on the deck, or sip wine beneath the elegantly lit and landscaped tropical foliage. Common areas provide Internet connectivity, a guest refrigerator, concierge services, and every morning breakfast is served poolside.

The Curry House –806 Fleming Street

A converted historic home only three blocks off Duval Street, Curry House Historic Bed & Breakfast offers a quiet respite from the revelry of Key West – but keeps you close enough to return anytime. Rooms are individually decorated, and most feature queen poster beds and doors to a porch or veranda. All but one has both air conditioning and a ceiling fan, and all have bar refrigerators. One room has a rather innovative skylight-topped shower stall that provides taller guests a unique view of Key West. A hot breakfast is chef-prepared and served each morning, and there’s a complimentary poolside happy hour each evening.

Island City House Hotel – 411 William Street

The three buildings of this guest house are decorated differently to reflect their histories: Arch House was once a carriage house, Cigar House once a factory, and Island City House itself a private home built for a wealthy merchant. The houses wrap around a tropical garden interlaced with winding brick pathways that eventually lead to a hot tub and a pool with an alligator mosaic on its bottom. There’s a picnic area, barbecue grills, and laundry facilities for the use of guests in all 24 suites.

THE LOWER KEYS & BIG PINE

Resorts: Little Palm Island Resort & Spa – Little Torch Key

Possibly the most exclusive and luxurious resort in the Florida Keys, Little Palm Island is an all-inclusive escape from the mundane. No televisions, telephones, alarms, or children under 16 will invade your vacation during your stay on this 5-acre resort traversed by Key deer and Roseate Spoonbills. Little Palm Island offers 28 tropical suites in 14 thatched-roof bungalows, all outfitted in the British Colonial style with private verandas. The two Island Grand Suites up the ante with his-and-her baths, garden hot tubs, and plenty of space to soak in the spectacular ocean view. On-site amenities include an Asian spa and steam bath, a pool, health club, piano bar, concierge, and a marina with water sports, diving, and fishing. Don’t miss the romantic restaurant, where the chef blends Caribbean flavors with French and Asian cuisine.

Hotels & Guest Houses: Parmer’s Resort – 565 Barry Avenue, Little Torch Key

 A collection of family-style waterfront cottages are scattered across 5 acres filled with tropical plants, 19 aviaries, and an inviting room for complimentary continental breakfast. This is a favorite of those looking for a friendly atmosphere and reasonable rates; many of Parmer’s clientele are repeat visitors. Parmer’s maintains telephone-free 45 units: 15 apartments, 12 efficiencies, and 18 motel-style rooms. All rooms feature decks or balconies, air conditioning, and cable television; most apartments and efficiencies have full kitchens. There are docks along the channel and a pool with sundeck.

Sugarloaf Lodge – MM 17 Bayside, Sugarloaf Key

Only 15 minutes from Key West, all of Sugarloaf Lodge’s 55 rooms are waterfront, with access to the pool, tennis courts, and miniature golf course. Dine on expertly prepared local seafood at the restaurant, relax in the cocktail lounge, or sip frozen libations at the tiki bar. The on-site marina offers charters trips for both divers wishing to investigate nearby Looe Key Reef and for backcountry fishermen in search of bonefish, permit, and tarpon. Dockage available.

Big Pine Key Fishing Lodge – MM 33 Oceanside, Big Pine Key

The Big Pine Key Fishing Lodge is a family-friendly combination of hotel and campground, with 16 rooms and 158 campsites (see the Camping link at left). The vaulted ceilings of the tile-floor units have queen beds downstairs and small sleeping lofts; kitchen equipment varies. There’s a pool and sundeck, a recreation room with evening movies, barbecue grills, an Internet room, and dockage at the marina. An ideal spot for fishermen and for families; three-day minimum stay required.

MARATHON & THE MIDDLE KEYS

Resorts: Hawk’s Cay Resort & Marina – Duck Key

Dotted with fresh and saltwater lagoons & pools, Hawk’s Cay comprises 60 acres and hundreds of rooms, suites, and villas. The guestrooms feature Caribbean-influenced interiors, balconies, and bar refrigerators, while the suites accommodate two to five people with a separate common room. Villas have full kitchens, laundry facilities, porches, and are available in different square footage sizes. On-site are five restaurants, two cocktail lounges, a full-service spa, a health club, and myriad other amenities. Hawks Cay activities include glass bottom boat tours, fishing, diving, and snorkeling trips, jet skiing, parasailing, golfing, tennis, interactive dolphin encounters, and a day camp for the kids.

Hotels & Guest Houses: Ocean Beach Club Hotel & Resort – 351 East Ocean Drive, Key Colony Beach

Standard guest rooms have either an island or ocean view, two queen beds, and a bar refrigerator. Suites have balconies facing the ocean, a full kitchen, a private king bedroom and a queen sleeper sofa in the sitting room. The resort is Oceanside of U.S. 1, and features a beach, a pool, a Jacuzzi, and a fishing pier. Adjacent are waterfront dining and a tiki bar.

Buccaneer Resort – MM 48.5, Marathon

This ten-acre resort features a private sandy beach and snorkel area surrounded by various types of single rooms, cottages, and villas. Choose between Gulf-view and beach-view; some larger units have partial kitchens, but all rooms are very spacious. Powerboat and Jet Ski rentals are available on-site, plus fishing and diving charters next door. Dockage and boat ramp on premises, along with tennis, volleyball, basketball, & badminton courts, barbecue grills, sun deck, and pool. The Buccaneer is known for its very reasonable rates and friendly staff.

Cocoplum Beach & Tennis Club – MM 54.5 Oceanside, Marathon

All twenty of the octagonal villas on the Cocoplum acreage feature living space on two elevated floors plus a ground floor for laundry facilities and storage of scuba and other equipment. On the second floor is a full kitchen, dining room, and screened patio. The top floor houses two bedrooms, two baths, and a living room with wet bar, sleeper sofa, and TV/VCR. Resort amenities include hammocks, cabanas, and tiki huts strewn across the white sand beach and around the oceanfront pool.

ISLAMORADA & THE UPPER KEYS

Resorts: Cheeca Lodge – Islamorada, Upper Matecumbe Key

 The recently renovated luxury beachfront bungalows and suites rest between vibrant gardens and koi-studded lagoons on the 27 acres of this resort. A variety of different room sizes and amenities will suit every vacationer, and nearly al the rooms have private balconies. A full spa offers facials, massage, and more, and two on-site restaurants supplement room service and poolside tiki bars. It’s a great choice for eco-conscious travelers, too, since Cheeca Lodge promotes environmental responsibility and specializes in eco-tours. Special children’s programs and a children’s pool allows adults to relax in peace, whether on the tennis courts, in the saltwater lagoon, the health club, the beach, or the hot tubs.

The Moorings – MM 81.6 Oceanside, Islamorada

Style yourself like the models that often pose on the white sand beaches of this former coconut plantation, and then retire to one of 18 cottages on the property. This laid-back resort offers guesthouses with one to three bedrooms and baths, full kitchens, and open-air porches on most units. Try your hand at tennis, cool off in the pool, and finish by grilling dinner on the beach.

Hotels & Guest Houses: White Gate Court – MM 76 Bayside, Lower Matecumbe Key

Pad down the 220 feet of white sand beach along Matecumbe Bight with your pooch – White Gate is one of the few pet-friendly hotels in the Keys. The seven units located in five villas and one duplex are outfitted with full kitchens and inviting patios with barbecue grills. Bicycles, paddle boats, and snorkel gear is provided. Dockage available along the lighted fishing pier; launch boats at Indian Key.

Pines & Palms Resort – 80401 Old Highway, Islamorada

Awarded the "Superior Florida Keys Lodging” designation in 2000, Pines & Palms offers accommodations from one-room efficiencies to a three-bedroom house. All the oceanfront cottage-style rooms feature full kitchens, and the Orchid Cottage is the resort’s secluded, ultra-luxurious getaway. Grill at the covered poolside cabana, which has a built-in barbecue, refrigerator, and sink. Boat ramp and docks provided.

Ragged Edge Resort & Marina – 243 Treasure Harbor Road, Islamorada

Tahitian architecture and ocean views for each of the ten units make the Ragged Edge a nice, quiet spot for relaxing in the Upper Keys. One-bedroom, two-bedroom, and studio apartments have either screened porches or large decks. Many rooms have full kitchens; all have at least bar refrigerators. This bare-bones spot doesn’t have a pool, in-room phones or televisions, but the fishing is renowned.

Photo of Key West Sunset

KEY LARGO & TAVERNIER

Resorts: Westin Beach Resort – MM 97 Bayside, Key Largo

The newly renovated Westin sits amidst lush tropical gardens and a hardwood hammock, through which winds a boardwalk nature trail. Large windows piercing the resort’s four stories bathe the luxurious interiors – baths are pure marble, and the widows open to views of Florida Bay, the island, or the hammocks. All rooms are large, but the Jacuzzi suites are larger yet, and feature private balconies. Adult and children’s pools with waterfalls, coral rocks, and bougainvillea sit beside a hot tub, tiki bar & grill, and the resort’s private beach. The resort offers diving and snorkeling gear and charters, complimentary boat dockage, and arts & crafts programs for children.

Marina del Mar Resort & Marina – MM 99.5 Oceanside, Key Largo

The upscale Marina del Mar Resort & Marina caters to boaters, fishermen, and divers. Amenities include tennis courts and a small gym, a pool, and Coconuts restaurants. Across the island is the Marina del Mar Bayside Resort, which features a private beach, volleyball, and pool – guests at either resort have reciprocal use of the other. All rooms are bright and clean, with tile and wicker furniture, and many feature private waterfront balconies and kitchens.

Marriott Bay & Beach Resort – MM 103.5 Bayside, Key Largo

 Most rooms have patios, some have bay views, and all have mini-bars, room safes, and other high-end amenities. Thousand square-foot suites have two bedrooms, a sleeper sofa, a full kitchen and bath, plus wrap-around porches. Massage and a day spa add to your relaxation, and you can work off dinners from Marriott’s many restaurants in their gym – or on the nine-hole golf course. The resort also organizes diving, snorkeling, and fishing excursions, and offers glass bottom boat rides and parasailing trips.

Hotels & Guest Houses: Kelly’s on the Bay – MM 104.2 Bayside, Key Largo

 All the tile-floored rooms feature bar refrigerators and Caribbean flair. Adjacent to Aqua Nuts Dive Center & their charter boats, Kelly’s draws a high percentage of sport diver clients, but it’s a great family hotel, too. Boat-accessible, and Kelly’s provides complimentary kayaks and “diver’s breakfasts” for guests. Heated pool.

Amy Slate’s Amoray Dive Resort – MM 104 Bayside, Key Largo

This mix of guest cottages, villas, and single rooms draws divers from across the country. The larger villas accommodate up to eight, with a queen bed & bath upstairs, two trundle beds, a second bath, a full kitchen, and a private screen porch below. Amoray operates a dive charter to John Pennekamp Coral Reef State Park, and a small beach on Florida Bay allows for fishing, swimming, snorkeling, and complimentary kayaking. Barbeque grills & picnic tables encourage outdoor dining.

Bay Breeze Motel Resort – MM 92.5 Bayside, Tavernier

 Rooms range from multi-bed Royal Caribbean suites with private decks and hammocks to queen-bed efficiencies with small kitchenettes. Amenities include a bougainvillea-ringed pool, a large private beach, and a boat ramp and dock for guest use. Grab your snorkel gear and the complimentary paddleboat and head out to explore “the deep hole,” a twenty-foot drop that attracts Key lobster, parrotfish, and starfish.

Jules’ Undersea Lodge – 51 Shoreland Drive, Key Largo

 Bed beneath the waters of Emerald Lagoon in this converted marine research vessel. Accommodates four and features a small kitchen and common room. Divers and novices alike can enjoy an evening undersea, and various packages are available, some of which include “mer-chef” service. Scuba instruction and honeymoon packages are available.

RATE BASICS

Generally speaking, room rates are higher between December and April, Fantasy Fest in October, Sport Lobster Season in July, and during national holiday weekends. Lower rates can be found especially during September & October, and sometimes November. From May to early August is considered a somewhat lesser “high season,” and rates will be adjusted accordingly. Rates are based upon double occupancy and do not include applicable taxes; minimum stay may be required during busy periods. Many hotels offer reduced rates for groups of for long stays; be sure to enquire. Accommodations in Key West are higher in cost than comparable rooms in the northern keys.

TIPS FOR CHOOSING A RESORT OR HOTEL IN THE FLORIDA KEYS

Those with boats should look for accommodations on the Florida Keys’ Oceanside, which is more heavily dotted with marinas, and the water is deeper. And if you’ve got a pet, but not a hotel that accepts them, contact local veterinarians as many offer boarding. Of course, those wishing for a longer stay should consider renting a condominium or private cottage; local real estate agencies can help find vacancies.