1. Breezy Palms Resort
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-2361 or (877) 412-73
Address: MM 80 Oceanside
Description: Quaint coral buildings with turquoise doors, trim, shake roofs, and screened porches mark Breezy Palms Resort, a cozy place nestled on 320 feet of oceanfront. The brightly wallpapered motel rooms, efficiencies, apartments, and cottages are clean, spacious, and well appointed, featuring rattan furniture and colorful island floral prints. Chickees and copious coconut palms pepper the property, which sits directly on the Atlantic Ocean and sports a sandy beach as well as a swimming pool. A brick barbecue, picnic table, and volleyball net add to the amenities; dockage is available for an additional fee. No straight inboards or personal watercraft, such as Jet Skis or WaveRunners, are permitted. Breezy Palms is accessible by boat. Children younger than age 13 stay free.
City: Islamorada, FL
Category: Accommodations
Address: MM 82 Oceanside
3. Chesapeake Beach Resort
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-4662 or (800) 338-33
Address: MM 83.4 Oceanside
Description: The elegant Chesapeake Beach Resort hugs the Atlantic on 6.5 acres of lushly landscaped grounds. This pristine 3-story, 65-unit resort is home to 13 villas, 44 guest rooms, and 8 suites. The Chesapeake sports 2 heated pools, a hot tub, tennis courts, on-site laundry facilities, and an outdoor gym, as well as a 700-foot sunning beach and a saltwater lagoon used for parking boats. A boat ramp and boat dockage are provided. Suites and villas offer full kitchens and have balconies or screened porches. Fishing, snorkeling, diving, and parasailing excursions, as well as sunset cruises, can be booked nearby. Use of kayaks and paddleboats are included in your stay. Chesapeake provides a playground for children, who can stay for free if they are younger than age 13.
City: Islamorada, FL
Category: Accommodations
Address: MM 75.6 Bayside
5. Hampton Inn & Suites Islamorada
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-0073 or (800) 426-78
Address: MM 80 Oceanside
Description: Situated directly at ocean’s edge, the Hampton Inn offers 59 suites, 16 standard rooms, and 4 wheelchair-accessible rooms with vistas of our endless sparkling sea. The common lobby area of the hotel sports a fishing theme with giant mounted dolphin, wahoo, and tarpon. Tables and comfy chairs flank a keystone fireplace, which is more decorative than functional, given the balmy Keys weather. A complimentary continental breakfast buffet is served here daily. Outside, guests enjoy a heated pool and spa, a tiki bar, and a palm-laden, sandy sunning area. You’ll also find a complete selection of water sports on the premises, including snorkeling and diving excursions, parasailing, and fishing charters. The popular Outback Steak House (305-664-3344) also is on-site.
City: Islamorada, FL
Category: Accommodations
Address: MM 81.2 Bayside
7. La Siesta Resort & Marina
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-2132 or (877) 278-03
Address: MM 80.2 Oceanside
Insider Pick:
Description: Tucked away amid the palm trees and the tropical foliage, you’ll find La Siesta Resort & Marina. There are a few options for lodging on the property, including one-, two-, and three-bedroom cottages and suites. The Insider tip here is to request cottage 101. It has been newly renovated with a navy-and-white nautical theme replete with white wainscoting and framed photos of fishing expeditions from yesteryear hanging on the walls. Cottage 101 also has a flat-screen TV, a king-size bed, a Mitchell Gold sleeper sofa, and a personal patio with a view of the marina and ocean beyond. And then there is the best amenity of all: your own personal hammock under the palm trees. Sure, there are water sports and a heated pool on-site as well, but the hammock beckons. How can you resist?
8. Lookout Lodge Resort
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 852-9915 or (800) 870-17
Address: MM 87.7 Bayside
Description: Situated next to Marker 88, one of the Upper Keys’ most distinguished restaurants (see the Restaurants chapter), Lookout Lodge is a clean, modestly priced motel of Spanish-influenced architecture. The resort’s 9 basic rooms feature decidedly 1960s decor and amenities. All suites have kitchenettes, tile floors and baths, and ceiling fans. A limited number of pet-friendly rooms (small pets only) are available. Steps lead from the resort’s raised man-made beach to the bay for swimming and snorkeling. The property features gas grills, picnic tables, and lounge chairs, but no swimming pool. Dock space, available for an additional fee, is limited and must be reserved in advance. Two weeks’ advance cancellation is required.
9. Ocean Dawn Suites
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-4844 or (866) 540-55
Address: MM 82.9 Oceanside
Description: Nothing looks like a million dollars in decorating until you have spent a million dollars! The owners of Ocean Dawn Suites started out just giving this property a facelift, but when the zeros started adding up, this once 8-room lodge reopened after a complete renovation with style and pizzazz, containing marble bathrooms, porcelain floors, custom furniture, and 40-inch flat-screen TVs. Outdoors, guests will enjoy a new clay tennis court, pool, croquet lawn, and a man-made beach, just yards from the Atlantic Ocean. It’s ideal for intimate wedding parties, offering a bridal suite that features a private balcony, kitchen, and Jacuzzi.
10. Pelican Cove Resort And Marina
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-4435 or (800) 445-46
Address: MM 84.5 Oceanside
Description: Perched beside the Atlantic Ocean, Pelican Cove Resort—constructed in concrete with a tin roof and Bahamian shutters—ensures a balcony and ocean view from almost every one of its 63 rooms. Behind the resort, steps connect the raised man-made beach to the ocean, where dredging for a once-used quarry has caused waters to run 30 feet deep. A swimming pool with sundeck, outdoor cabana bar and cafe, poolside hot tub, volleyball net, and water-sports concession all front the beach. Complimentary coffee and juice are offered in Pelican Cove’s office 24 hours a day. Children younger than age 17 stay free at Pelican Cove. Limited boat dockage is available to guests for an additional fee.
11. Topsider Resort
City: Islamorada, FL
Category: Accommodations
Telephone: (305) 664-8031 or (800) 262-98
Address: MM 75.5 Bayside
Description: The 20 octagonal, elevated time-share villas at Topsider Resort flank a wood boardwalk that marches from the secluded parking lot to the crystalline waters of the Gulf of Mexico. Units are identical in layout. Each features 2 bedrooms, 2 baths, a dining area, living room, full kitchen, and a washer and dryer. The units are updated on a rotating basis. Be sure to inquire as to when your unit was last renovated before booking. Guests at Topsider Resort enjoy an elevated heated pool and spa, a tennis court, children’s swings and slides, grills, picnic tables, and bayfront wood lounges for sunning on the sandy lagoonside beach. Free boat dockage is available on Topsider’s long pier. Minimum stay here is 3 nights, but most guests opt for a week’s sabbatical.
City: Islamorada, FL
Category: Accommodations
Address: MM 76 Bayside