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A private tropical getaway awaits you on the Florida Keys, with some of the most splendid villas and condo rentals available on the sandy shores. For those looking for a decadent getaway, Luxury Rentals by At Home in Key West has a variety of accommodations all impeccably maintained. The properties at Rent Key West Vacations feature a blend of privately owned accommodations between Old Town Key West and the beach itself. For a locally owned and operated business, Vacation Homes of Key West offers a grand variety of condos and villas with shared amenities like golf and swimming pools, as well as gorgeous beachfront locations. A private getaway to a tropical paradise is awaiting you in the Florida Keys, so book your vacation today!

Showing 1-20 of 23 Villas and Condos

Chesapeake Beach Resort

Islamorada, Florida, United States
$179
1-866-588-0250

At Chesapeake Beach Resort, 13 private villas offer all the amenities of home in a spectacular Florida Keys setting. Enjoy fully-equipped kitchens,... more

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Rent Key West Vacations

Key West, Florida, United States
$150
1-866-980-7608

Not sure what to expect? The condos and homes of Rent Key West Vacation offer exceptional value for your next getaway. Enjoy all the space and... more

Resort features:
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Historical
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Luxury Rentals by At Home in Key West

Key West, Florida, United States
$175
1-877-695-2791

At Home in Key West offers an impressive selection of luxurious vacation homes throughout the Key West area. Their rentals range in style and size so... more

Resort features:
  • Beach
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
$170
1-866-967-3004

Keys Holiday Rentals features an impressive selection of luxurious condominiums to choose from on your Florida vacation. These units are all... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Vacation Homes of Key West

Key West, Florida, United States
$250
1-866-241-1140

You'll find a wide selection of villa and condo vacation rentals available through Vacation Homes of Key West, all perfect for your next Florida Keys... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday
  • Island
  • Villas and Condos

Florida Keys Vacations Inc.

Marathon, Florida, United States
$251
1-855-478-7640

Whether you're looking for a sprawling five-bedroom vacation home, or a cozy one-bedroom condo, Florida Keys Vacations Inc has a vacation rental to... more

Resort features:
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Island
  • Villas and Condos

Parrot Key Resort

Key West, Florida, United States
$179
1-866-939-3715

Overnight accommodations at Parrot Key Resort consists of 148 of some of the most spacious guest room options in all of Key West! The varieties of... more

Resort features:
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Tranquility Bay Beach House Resort

Marathon, Florida, United States
$279
1-866-452-5369

Tranquility Bay Beachhouse Resort offers a range of two and three bedroom beach houses. These spacious accommodations are located right along the... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

La Concha Hotel & Spa

Key West, Florida, United States
$213
1-305-296-2991

Inspire your next adventure tale with the richly decorated decadence of La Concha's rooms and suites filled with classic charm and modern luxuries.... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Island
  • Spa
  • Villas and Condos

Key West Vacation Rentals

Key West, Florida, United States
$169
1-305-296-9292

You'll find a unique selection of luxury accommodation options to choose from during your next Florida vacation at Key West Vacation Rentals. These... more

Resort features:
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Sheraton Suites Key West

Key West, Florida, United States
$149
1-305-292-9800

Sheraton Suites Key West is the only suite-only hotel in the Keys, and features 184 comfortably-styled rooms. Every room includes a wet bar,... more

Resort features:
  • Beach
  • Family
  • Golf
  • Meetings
  • Wedding
  • Nature
  • Pet Friendly
  • Villas and Condos

The Inn at Key West

Key West, Florida, United States
$118
1-305-294-5541

Old elegance and island adventure flavor the unique and charming Inn at Key West accommodations. A host of the best boutique amenities and decadent... more

Resort features:
  • Beach
  • Family
  • Nature
  • Luxury
  • Holiday
  • Villas and Condos

The Reach Resort A Waldorf Astoria Resort

Key West, Florida, United States
$179
1.866.397.6427

The guest rooms and suites at The Reach Resort offer either stunning ocean, tropical pool or lush courtyard views. To ensure a comfortable and... more

Resort features:
  • Beach
  • Meetings
  • Family
  • Fishing
  • Holiday
  • Honeymoon
  • Luxury
  • Romantic
  • Spa
  • Wedding
  • Villas and Condos

Coconut Bay Resort Key Largo

Key Largo, Florida, United States

Overnight accommodations at Coconut Bay Resort Key Largo consist of six guest rooms and cottages. These cozy retreats boast all the modern amenities... more

Resort features:
  • Beach
  • Nature
  • Wedding
  • Villas and Condos

KeysCaribbean

Marathon, Florida, United States

KeysCaribbean features a wide range of incredible beachfront condos and villas. With the air and feel of a luxury resort, these units are ideal for... more

Resort features:
  • Beach
  • Family
  • Holiday
  • Luxury
  • Romantic
  • Villas and Condos

The Southernmost House

Key West, Florida, United States
$239
1-305-296-3141

You can't help but live a life of adventure in such an unforgettable setting! Let local character charm your heart with the unique personalities of... more

Resort features:
  • Beach
  • Nature
  • Romantic
  • Luxury
  • Honeymoon
  • Villas and Condos

The Westin Key West Resort & Marina

Key West, Florida, United States
$151
1.305.294.4000

With 178 guest rooms and suites, the Westin Key West Resort and Marina has a unit that fits all of your needs. All rooms include Westin bathrobes,... more

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Fishing
  • Romantic
  • Luxury
  • Spa
  • Villas and Condos

The Banyan Resort

Key West, Florida, United States
$190
1.866.371.9222

Choose the suite accommodations that fit all of your needs when you stay at Banyan Resort. Whether you and your special someone are looking for a... more

Resort features:
  • Beach
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Holiday
  • Timeshare
  • Villas and Condos

The Hammocks at Marathon

Marathon, Florida, United States
$120
1.800.456.0009

With plenty of villas and condos to choose from, you'll find the perfect room to fit your style and budget. Take in breathtaking views from your... more

Resort features:
  • Beach
  • Family
  • Fishing
  • Island
  • Villas and Condos

1800 Atlantic Condominiums

Key West, Florida, United States
$195
1-800-433-2819

Spacious, two- and three-bedroom Florida Keys condos feature two full baths, fully equipped kitchens and cable TV. There are plenty of ways to enjoy... more

Resort features:
  • Beach
  • Family
  • Luxury
  • Romantic
  • Villas and Condos

Showing 1-20 of 23 Villas and Condos

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