Holiday rentals in Key West

Paradise in the Keys

Welcome to Pura Vista otherwise known as Pure Views. Come enjoy a delightful stay at this beautiful direct waterfront property in the Florida Keys for your getaway. Breath taking views of the Atlantic Ocean and direct ocean access to the best boating activities in the warm turquoise waters of the Florida Keys. Well equipped with commodities to help your stay be the best. A great location to discover everything the Florida Keys has to offer. We look forward to hosting your stay! VACA – 22 - 376

Villa 5008 on Duck Key - Boat Slip Available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to relax & enjoy waterfront living in this corner condo in historic Downtown Key West. Walk or bike everywhere—less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. On-site amenities include a heated pool, tiki bar & grills, parking, secure keyless entry, building elevator. Please note: The condominium dock will be under construction beginning April 27, 2026 for approximately 30 days; dock access will be unavailable and daytime construction noise is expected.

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Hidden Beach Duplex, Best Place in Key West

Go to sleep and wake up smiling listening to the waves. Just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

Aquahouse Paradise easy access to the ocean

Take it easy at this canal front with quick acces to the ocean unique and tranquil getaway. Big Pine Key, know it for the key deers, one of the only 2 places in the entire world where you can interact with this endangered species. you can feed it during night they love bread and eggplants, here you can enjoy the florida weather conditions all year long. lot of activities. only 30 miles away from Key West. 2 miles from supermarket,pharmacy, hardware and auto parts.

Duval Corner - Pet friendly with Balcony

Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

Vacation home Island Suite 16

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

See our home on HGTV's "Vacation House for Free", (Rental Lisc#VACA-20-690) BRING YOUR BOAT TO OUR PRIVATE 60 FOOT DOCK WITH 30 AMP SHORE POWER OUTLET. We call our home "Bahama Breeze" because that's what you feel blowing in as you spend your vacation at this Oceanside single family home.

Palm Garden retreat with Hot Tub & Prime Key West

Welcome to the Poolside Hide-Away @ Palm Gardens. A lovely one bedroom, one bath historic condo on the edge of Old Town just blocks to Duval St and the Historic Seaport. Private hot tub and community pool for your enjoyment.

Beach Club Ocean Front 2BR Condo

Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.

TortugasHarbor Light Suite

Luxury 1BD/1BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing Views.