Resort holiday rentals in Key West

Key Largo Cottages w/ Free Sailboat, Kayaks + More

The Mermaid is one of the cottages in Key Largo Cottages located on the bay side of Key Largo near some of the best dive/snorkel sites, island excursions, bars, restaurants, & the Everglades. A stay here comes with unlimited use of our kayaks, canoes, paddle boards, snorkel gear, some fishing gear, &, of course, the use of one of our 22' sailboats, if you have recent sailing experience on keel boats! You won't find a better deal in the Keys! (This is NOT a dog friendly cottage.)

Parrot's Perch

The Parrot’s Perch (formerly Zeke’s Retreat) is a sun filled suite with soaring ceilings features a living room with a queen sleeper sofa, a wraparound porch with a hammock, a kitchenette with a convection \microwave oven and a bedroom with a king size bed with private balcony overlooking the palm trees. Sleeps 4 people. Complimentary breakfast included. Enjoy 3 pools, wifi, and smart TVs. Very limited paid parking available onsite on a first come first serve basis.

2BR Villa Hyatt Windward Pointe

2BR, 2Ba Villa (1065 sq ft) with full kitchen at 4-star Hyatt Windward Pointe Resort. Infinity-edge pool, outdoor grills, on-site restaurant and amenities. 1 BR has King bed, 2nd BR has queen bed. Each BR has attached full bathroom. Villa includes dining room, living room and furnished balcony with partial ocean view. Quiet location, 1.5 miles to popular Smathers beach, 5 miles to Mallory Square (with attractions, excursions, and nightlife).

Hyatt Windward Pointe - Key West - Amazing Resort!

Atlantic ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium offering a master suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full bath. Deluxe amenities include full kitchen, dining area, living room with TV and stereo CD player, furnished balcony and wireless Internet

Coral Townhome

Built as a townhouse-style apartment with two levels, the Coral Townhome includes one bedroom with a king-size bed and a full bathroom, while the downstairs level offers a private bedroom in the back with a full-size mattress bunk bed, a full kitchen, another bathroom, and a living room equipped with a sofa bed. Featuring two bedrooms, these townhouses accommodate up to five guests.

Charming 2 Bedroom Suite Beach Resort

Our private tropical paradise, reminiscent of days gone by, sits quietly and serenely on the Atlantic side of Key West. Here you will find a blend of old island architecture, lush vegetation and quiet walkways flowing onto bright white verandahs. Each of our layouts offers its own touch of uniqueness, be it a high-pitched ceiling, a private balcony or a spectacular panoramic view.