Resort holiday rentals in Key West

Studio Galleon, Hot Tub, In Town, Pool, Marina

The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios house two people and are equipped with a small refrigerator, coffee maker and microwave oven. One-bedroom suites sleep up to four while most two-bedroom suites sleep up to six, while both include a full kitchen, dining area and decked out living area. Furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.

Enticing two Bedroom at Hyatt Sunset Harbor!

We are able to offer reservations in weekly increments with arrivals and departures on Fridays, Saturdays, and Sundays only. Discover a relaxing oasis overlooking the Gulf of Mexico in the heart of Old Town, steps from the shops, galleries, and cafes of Duval Street, and close to the nightly sunset celebration at Mallory Square. Hyatt Sunset Harbor’s spectacular gulf coast setting is matched only by the gracious service, top-tier amenities and meticulous attention to detail.

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.)

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).

Katie's Kottage

Relax in this private cottage located in the heart of Old Town Key West. The cottage sports 2 private bedrooms with queen beds, 2 bathrooms, a queen pullout couch, full living room and kitchen, & deck area that surrounds one of our pools. Enjoy our daily complimentary breakfast, 3 pools, wifi, and TV. Perfect for a group of up to 6 or families! We have paid parking first come first serve, or you can find free street parking.

HVC The Beach House- your home away from home!

You'll enjoy your time at this cheerful getaway. The property has 3 floors with beautiful views. Suites come fully equipped with a kitchen, 2 BR, 2 BA. King beds in Brs and a double sleeper sofa in living area *PLEASE NOTE- Once you request specific dates, I reach out to Hyatt Vacation Club for availability. We own points, not a specfic unit. * A cleaning of $60 is due on checkout.

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.

Studio - Hyatt Residence Club Key West

Tropical Key West welcomes you to a classic Florida studio condominium, offering a plush king-size bed, casual living area with TV and DVD player, and kitchenette with microwave and mini-refrigerator. Amenities include: onsite washer and dryer, coffeemaker, ceiling fans and wireless Internet access

3 BEDROOM 3 BATHROOM ISLAND TOWN HOME

This Island Town Home is conveniently located in Long Key which is in the middle of the Florida Keys right in between Islamorada and Marathon. It is a 2-hours drive from Miami airport and only 90 minutes from Key West. This mid-way location is perfect for exploring all the Florida Keys.