Florida Keys Hotels › Romantic Hotels
29 Hotels Found
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Cheeca Lodge & Spa

Cheeca Lodge & Spa Rating: 4.5 Pearls

The 114-room Cheeca Lodge was one of the original luxury properties on Islamorada, dating to 1946 and earning plenty of celebrity cachet over the years (high-profile guests have included George W. Bush). The property was rebuilt after a fire gutted its main building in 2009, and now has bright, spacious rooms with tropical-luxe decor and massive bathrooms. The lush grounds are especially pretty at night, with Tiki-torch-lit paths. But the hotel's beach is manmade -- there's even a rock ledge on the water's edge -- making it muddy at times and less than ideal for swimmers and waders. And the family pool can get crowded; those traveling without children will probably prefer the much calmer adult-only pool.

Casa Marina Resort - a Waldorf Astoria Resort

Casa Marina Resort - a Waldorf Astoria Resort Rating: 4.5 Pearls

The 311 rooms of the Casa Marina Resort have a light, sophisticated, but still island-y feel, with neutral tones, sheer curtains, and sleek hardwood or tiled floors. The resort also offers great in-room amenities, including free Wi-Fi, flat-screen TVs, and espresso machines. Although bathrooms aren't anything grand (just simple walk-in showers or shower/tub combos), they're clean and sleek. The resort's grounds are beautiful, with palm trees and lush foliage, and lead to a rare amenity in Key West -- a swimmable beach. Although it's too rocky to wade into the water, a long dock extends to sandier bottoms.

Sunset Key Guest Cottages, a Westin Resort

Sunset Key Guest Cottages, a Westin Resort Rating: 4.5 Pearls

This 40-room resort caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities. It is located on Sunset Key, a residential island off Key West, and is affiliated to the Westin Key West, with which it shares some features, such as the fitness center and the restaurants (though only guests of Sunset Key can use the on-site amenities; Westin guests do not have access to them). The hotel itself has wonderful amenities, including a lovely pool, a gorgeous beach with palm trees and clear waters, and a pleasant spa. Its location, though idyllic and exclusive, might be somewhat inconvenient for travelers who want to be close to shops and restaurants (the hotel only has one eatery on-site).

Little Palm Island Resort & Spa

Little Palm Island Resort & Spa Rating: 4.5 Pearls

Reachable only by boat or seaplane, Little Palm Island Resort & Spa is located on a private island where wild key deer roam. It includes 30 luxurious suites, many with private oceanfront verandas. A favorite getaway for celebrities, it provides a secluded place to unplug from the world (use of technology is discouraged) and experience a romantic vacation in a lush, tropical environment.

The Mermaid & The Alligator

The Mermaid & The Alligator Rating: 4.0 Pearls

The Mermaid and The Alligator is a nine-room upscale bed and breakfast housed inside a historic Victorian estate. The owners have taken great care to renovate the home with bold and vibrant decor and updated furnishings. Located on Truman Street, three blocks from popular Duval Street, the home is a quiet and peaceful area that is steps from the heart of the entertainment district. There is a lush interior garden with hammock, lounge chairs, and plunge pool, but there are no on-site restaurants for lunch and dinner and the cancellation policy is strict.

Casa Morada

Casa Morada Rating: 4.0 Pearls

Inspired by a laidback Caribbean lifestyle, Casa Morada is an upscale 16-suite boutique hotel that’s perfect for couples looking for a romantic getaway, whether for a honeymoon or just because. Situated right next to the ocean in the middle of the Florida Keys on Islamorada, the hotel provides a peaceful and serene atmosphere with hanging hammocks and lots of fun and free activities like yoga classes, kayaking, and bicycle rentals. Compared to nearby hotels, this property offers great value with spacious and upscale rooms with water views.

Tranquility Bay Beach House Resort

Tranquility Bay Beach House Resort Rating: 4.0 Pearls

Spread across 12 waterfront acres in the Florida Keys, Tranquility Bay Beach House Resort is a collection of upscale tropical Victorian-style homes divided into multi-story two- and three-bedroom suites with full kitchens and water views. There are also a handful of guestrooms without ocean views. With a private beach, three pools (including one adults-only), and an array of on-site water sport activities available, the property is a great fit for vacationing families. A waterfront tiki bar is a scenic spot to sip cocktails, but a car is needed to explore outside of the resort.

Marriott Key Largo Bay Beach Resort

Marriott Key Largo Bay Beach Resort Rating: 4.0 Pearls

This 153-room property is located in northern Key Largo, a short drive from the John Pennekamp Coral Reef State Park, and close to shops and restaurants. Not a lot stands out, but there are a few perks -- like a diver’s center on-site, an adequate spa, and a nice private beach (albeit a tiny one, with little room for swimming). Big rooms have flat-screen TVs, free Wi-Fi, and nicer decor than other mid-range chains in the area -- but many bathrooms could use a renovation. Upgrading to a suite will give you a full kitchen and a large sitting area, but smaller sleeping quarters. Book a room with an ocean view to enjoy the beautiful Key Largo sunsets (and avoid facing the nearby highway).

The Reach, a Waldorf Astoria Resort

The Reach, a Waldorf Astoria Resort Rating: 4.0 Pearls

The Reach offers respite from rowdy, gaudy Key West with its brand of relaxed sophistication and its beachfront location. Its 150 rooms are what you would expect from the Waldorf Astoria crowd: spacious, modern and clean, with generic high-end furnishings and comfortable beds outfitted in crisp linens. They feel just a tad less upscale than those at the Casa Marina, its sister hotel next door (partly due to the use of carpet, rather than Casa Marina's tile or wood), but the hotel's private white-sand beach with a pier for fishing is just as nice.

Marquesa Hotel

Marquesa Hotel Rating: 4.0 Pearls

Refurbished from 1884 conch houses, the Marquesa Hotel is a compound of four buildings surrounding lovely interior gardens and two pools. A narrow staircase off the lobby leads to the individually decorated rooms. Light and airy rooms feature flat-screen TVs, mini-fridges, and cozy sitting areas with ottomans. Bathrooms are basic and clean with shower/tub combos and marble sinks. Suites have private terraces with cute wicker furniture and some are adjacent to one of the hotel's pools. An appealing on-site restaurant, Cafe Marquesa, serves fresh local seafood. No children under 14 are allowed at the hotel, providing this property with a distinctly romantic feel. Free Wi-Fi and parking add value, and the Old Town location two blocks from Duval Street is convenient.

Dates


Oyster Pearl Rating

  • Award-Winning

What's Your Style?

  • Romantic
  • Beach
  • Luxury
  • Resort
  • Value
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Locations

  • Duck Key
  • Islamorada
  • Key Largo
  • Key West
  • Little Torch Key
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Amenities

  • Air Conditioner
  • Babysitting Services
  • Balcony
  • Bar at Pool
  • Basic Television
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Brands

  • Courtyard by Marriott
  • Hyatt
  • Marriott
  • Noble House
  • Southernmost Resorts
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