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Showing 1-15 of 26 Luxury Resorts

Chesapeake Beach Resort

Islamorada, Florida, United States
77
Good
706 Reviews
Compare
$179

Savor the lavish surroundings at Chesapeake Beach Resort. Here, you can feel right at home in a spacious villa, relax on your private terrace or lounge in the tiki hut. The beautiful oceanfront setting lets you sink your toes in the sand or unwind in a swaying hammock. With two onsite pools, outdoor exercise equipment, a tennis court and much more,... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 65 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Islamorada
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Hawks Cay Resort

Duck Key, Florida, United States
79
Very Good
2221 Reviews
Compare
$299

Resting on a 60-acre island in the Florida Keys, there's very little about Hawks Cay Resort that doesn't scream luxury. This incredible destination features a wide selection of guest rooms and villas, each with an assortment of modern amenities that will make you feel right at home. Six spectacular onsite pools await for you to enjoy, along with... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 420 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Duck Key
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Golf
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Health
  • Diving
  • Holiday
  • Island
  • Spa
  • Villas and Condos
  • Waterpark

Tranquility Bay Beach House Resort

Marathon, Florida, United States
90
Excellent
627 Reviews
Compare
$279

Tranquility Bay Beachhouse Resort's beautiful setting on the Gulf of Mexico offers you a truly luxurious beach vacation unlike any you've experienced before. Choose from a variety of spacious two- and three-bedroom beach homes that feature kitchens, flat-screen HDTVs, and much more! Stop on by the Butterfly Café- rated as Marathon's best... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 106 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Barefeet Rentals

Key Largo, Florida, United States
Compare
$175

Ranging from a variety of styles and sizes, Barefeet Rnetals offers everything you expect in a luxurious getaway. Choose from waterview rentals to private homes to accommodations that offer their own dockage for your convenience. With multiple bedrooms and baths, modern gourmet kitchens, and spacious living rooms, you're sure to find the place... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 134 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Miami
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving

Rent Key West Vacations

Key West, Florida, United States
Compare
$150

Rent Key West Vacations offer numerous options that will have you feeling like you're in the lap of luxury. Choose properties with granite countertops, fine linens, jacuzzis and more. Make sure that every element of your Key West vacation is nothing but the finest when you stay with Rent Key West Vacations.... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 85 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Caribbean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Holiday
  • Villas and Condos

Parrot Key Resort

Key West, Florida, United States
Compare
$179

From the four incredible swimming pools to delightful poolside dining at the Café Blue to an unbeatable oceanfront location, you'll find luxury around every corner at the Parrot Key Resort. Choose from a guestrooms and one- and two-bedroom suites that offer modern amenities to keep you comfortable. Rent equipment right onsite for fun watersports,... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 148 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

La Concha Hotel & Spa

Key West, Florida, United States
Compare
$213

Built with total comfort in mind, the Crowne Plaza Key West La Concha has been updated to encourage relaxation, entertainment, and rejuvenation. Spend time with your family in this beautiful hideaway complete with granite countertops, private balconies overlooking the sea, dark wood plantation furnishings, and peacock colored ceilings. Find... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 160 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Nature
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Island
  • Spa
  • Villas and Condos

Garden House Bed & Breakfast

Key West, Florida, United States
Compare
$168

The Garden House is an elegant retreat for your Key West vacation. Here, you will choose from twelve charming rooms, each with its own selection of amenities such as cable television and mini-refrigerator. Onsite, the lagoon-shaped pool provides you with a place to unwind easily, while the spacious patio area lets you soak up the sun as you indulge... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 12 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Island

Vacation Homes of Key West

Key West, Florida, United States
Compare
$250

Vacation Homes of Key West prides themselves on offering travelers with an impressive selection of accommodations that are beyond all your expectations. These are not just rentals where you can rest your head; these are charming beachfront cottages with cozy decks, spacious multi-bedroom condominiums with shared community pools, and luxurious... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 59 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Curry House

Key West, Florida, United States
Compare
$178

The Curry House is a charming retreat that's welcomed guests since the mid-1900s. It's nine bedrooms each offer its own unique style and amenities that make it special. You will love private bathrooms and balconies, ceiling fans, and luxury linens. Enjoy breakfast cooked up everyday in the commercial kitchen and relax out on the lounge chairs... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 9 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Island

Sunrise Suites Resort

Key West, Florida, United States
Compare
$213

The spacious two-bedroom, two-bathroom condominiums at Sunrise Suites Resort ensure your complete comfort and convenience. These charming rentals are equipped with a full kitchen, a private balcony, and cozy furniture to ensure you feel right at home throughout your stay. Enjoy the views from your balcony, and whip up your favorite meals in the... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 48 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon

iTrip - Islamorada

Islamorada, Florida, United States
$115

These spacious condos and vacation homes offer all the comforts of home and more! Flat-screen televisions, cable, Wi-Fi access, and full kitchens make you feel at home. Jacuzzi tubs, private beach access, tennis courts, swimming pools, and balconies remind you that you're on vacation. Stay in these chic settings and uncover your utopia! ... more

The Inn at Key West

Key West, Florida, United States
$118

The Inn at Key West offers quality amenities like 42 inch plasma televisions, access to the state-of-the-art facilities overlooking the ocean, a secluded pool to play in and so much more! High quality staff and a concierge service to make sure you can enjoy the Key West to the fullest! Let them book your glass bottom boat tour or romantic sunset... more

The Moorings Village

Islamorada, Florida, United States
$419

From fresh, local fare featuring Spanish, African, and Caribbean cuisines, to the phenomenal, French fusion of Pierre's, the Morado Bay Beach Cafe, and Full Mon Party there are a flurry of restaurant options, right onsite, for you to choose from. Join in the fun with an evening full of Brazilian Capoeira dancers, Bahamian Junkanoo Parade, or a... more

$251

Imagine yourself sipping your morning coffee as you relax in a comfortable Adirondack chair on the private porch of a charming cottage as a basket of muffins and other breakfast goodies are delivered to you along with a daily paper. All this and more waits for you at Sunset Key Guest Cottages!... more

Showing 1-15 of 26 Luxury Resorts

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