20+ Coolest Florida Keys VRBO Rentals Featuring Beachfront Homes, Pools & Private Islands!

Are you searching for the coolest VRBOs in the Florida Keys? From beachfront homes with pools to renting an ENTIRE island – there are some crazy VRBOs in the Keys!

No need to travel far when you’re in the mood for a dreamy Caribbean escape, The Florida Keys are an amazing tropical paradise that are brimming with culture and history. Plus, you get to experience the beach life and the best key lime pie in the world — who would want to miss out on that?

And since you’re on island time, your vacation can be as laid back or thrilling as you want it to be. Go fishing, snorkeling, swimming, or hang on a hammock by day, then sample the freshest seafood and go tiki bar hopping at night. You can also tour galleries, hike through nature preserves, and witness spectacular sunsets on an oceanfront deck.

To make your trip to the Florida Keys even more memorable, you’re going to want a cool place to stay! For this post, we’ve rounded up the coolest Florida Keys VRBO rentals for you to choose from! Enjoy, and let us know which is your favorite VRBO in the comments.

*Disclosure: some of these links are affiliate links. Meaning, if you click a link and make a purchase, Have Clothes, Will Travel gets a very small commission at no extra cost to you. Thank you for supporting the brands that make this blog possible!

20+ Coolest Florida Keys VRBO Rentals

Unique Stays

4-bedroom Yacht with Private Pool and Tiki Hut – Stock Island

Every minute is bliss inside this 4-bedroom catamaran fully equipped with a kitchen and supplies. After cruising along with the majestic views of Key West, take time to unwind in the yacht’s amenities – including a swimming pool, sauna, and fitness center. Guests will also have their own restaurant and bar as well as a private tiki hut for cocktail parties.

Click here for more info on this Yacht!

3-bedroom Resort on Private Seabird Key Island – Marathon

Renting a whole island to yourself may seem like a dream, but it’s entirely possible in this private 10-acre tropical island getaway with a sandy beach, garden, and boat dock. It has an exquisite 3-bedroom island home that can accommodate up to 10 guests. It’s also furnished with multi-level porches and decks that lend to spectacular 360-degree views of the Florida Bay and the Gulf of Mexico. Seabird Key is also eco-friendly; guests are encouraged to recycle, and the resort employs solar panels and cistern to conserve resources.

Click here for more info on this VRBO.

Private Paradise Island with 3-bedroom Bahamian-style House – Marathon

Spend time on this perfectly secluded and private island with over 5000 square feet of living space. Your island time is sure to be an unforgettable one as it includes a 2700 square feet veranda with 360-degree views of the surrounding ocean as well as a 3-bedroom Bahamian style house with sliding glass doors, a boat dock, helicopter launch pad, and a pool!

Click here for more info on this VRBO.

Luxury House Rentals with Pool

Elegant 5-bedroom “Southernmost Belle” Home with Heated Pool – Key West

Nestled behind a palm canopy is a private 5-bedroom home in the Historic Seaport area of Old Town Key West. Guests will appreciate the peace and privacy this gated yet charming property brings. Guests can also relax in style in one of the two expansive porches with lush tropical landscaping, cook something up in the gourmet kitchen, or swim in the heated pool.

Click here for more info on this Florida Keys VRBO.

Elegant “Casa Loca” 3-bedroom Home with Pool – Key West

Casa Loca is a picturesque 3-bedroom, 3-bathroom home in Duval in Old Town Key West. It’s in a prime location ornamented with a charming tropical garden and modern amenities including a private heated pool, galley kitchen, and an Instagrammable front porch for coffee or cocktail breaks. Guests may feel as if they’ve booked into a cozy luxury hotel with their very own pool to party in.

Click here for more info on this Florida Keys VRBO.

Historic 6-bedroom Skelton Home with Private Backyard Pool – Key West

Just steps from Duval Street is this historical 6-bedroom, 4-bathroom home newly updated to include Victorian accents, hardwood floors, and exposed Dade County Pine walls. It’s spacious enough for guests’ enjoyment; it also features a private backyard pool, two living rooms, and shaded outdoor patios and porches—an ideal location for intimate family gatherings or weddings.

Click here for more info on this Florida Keys VRBO.

Privately Gated 3-bedroom House in Sunset Beach Paradise with Pool – Key Largo

Swaying palms lined up along a white sandy beach sets the mood in Sunset Beach Paradise, a privately gated property with a 3-bedroom home, fully equipped kitchen, and a swimming pool. Outside is a covered patio with barbecue amenities. The home is also steps away to the pristine Florida Bay beach where you can relax on a hammock, go swimming, snorkeling, or watch the sunset in the comforts of your own backyard.

Click here for more info on this Florida Keys VRBO.

Oceanfront 13-bedroom Home with Pool on Sombrero Beach – Marathon

Right in the heart of Florida Keys is Marathon Island, a 7000 square feet property with 13 bedrooms, 10 bathrooms, and access to an 80-foot private heated pool with a jacuzzi. The space is tastefully decorated with Italian marble floors and marble field-stone walls and with modern amenities to host large parties. It’s also within walking distance to Sombrero Beach, five-star restaurants, and tiki bars.

Click here for more info on this Florida Keys VRBO.

4-bedroom Vintage Key West Retreat with Lagoon-style Pool – Key West

Nautical accents with old-world charm make up this 4-bedroom vintage rental in Key West. The “Captain’s Quarters” is furnished with Dade County pines and high ceilings and comfortably sleeps up to 10 persons in its 4-bedroom, 3-bathroom setup. A winding path leads guests to a lagoon-style heated pool surrounded by a comfortable composite deck and outdoor seating.

Click here for more info on this Florida Keys VRBO.

3-bedroom “Pilar’s Secret” Home with Private Pool – Downtown Key West

This cozy 3-bedroom abode is named after Ernest Hemingway’s fishing boat, Pilar, and is a hidden oasis just off the famous Duval Street. French doors open to a lovely pool area with chaise lounges and chairs surrounded by tropical greenery. There’s also a fully equipped kitchen with appliances and tools to make a fantastic meal and a barbecue grill that’s perfect for a poolside cookout.

Click here for more info on this VRBO.

Luxury 5-bedroom “Nautical Splender” with Pool – Raccoon Key

A 5-bedroom waterfront home with nautical accents; the property is located in a luxury gated community and has a dock for boating. It’s a private paradise that can accommodate up to 16 guests. It also has a heated pool and expansive covered porches to take in the spectacular views of the waters and surrounding lush tropical landscaping.

Click here for more info on this VRBO.

Classic 1910 Revival 5-bedroom Home with Pool – Key West

“Seaside Place” is a classic 5-bedroom revival style home built in 1910 just off Duval Street with stunning Atlantic Ocean views. This 2700 square feet property still retained its old charms seen in its wood peg structure and traditional balcony with gingerbread trimmings. Amenities include a heated pool with waterfall, wraparound balconies with seating, and a refreshing cabana bathroom.

Click here for more info on this VRBO.

Two-story Tropical Beach House with Pool – Key West

A sun-kissed two-story property nestled in the gated community of historic Truman Annex. Swaying palm trees surround the property, while its open floor plan brings in natural lighting that will have guests feeling right at home. Wood floorings and a high ceiling makes up its 4-bedroom, 4-bathroom set up, while its magnificent pool and lounging space outside will certainly quench the guests’ island cravings.

Click here for more info on this VRBO.

Private 5-bedroom Home with Heated Pool and Ocean Views – Islamorada

A luxury 5-bedroom, 5-bathroom home based in a private paradise beach in Islamorada. Aside from the gorgeous oceanfront heated pool, each room in the house lends to spectacular 180-degree water views. On one side of the property is a natural preserve, and the private beach itself is a protected nesting beach for turtles!

Click here for more info on this VRBO.

Luxury Oceanfront Home with Pool and Private Beach – Sugarloaf Key

A 4-bedroom, 5-bathroom luxury home located between two national parks, the Great White Heron and Loey Key National Park. This beautiful home by the sea will have guests basking under the sun on the property’s private beach or dipping in the private heated pool with a view. There’s also a game room with a wet bar and a grill should guests want to dine outside with views of the ocean.

Click here for more info on this VRBO.

Cottages

Traditional 4-bedroom Chick-A-Pea Cottage with Pool – Key West

A renovated Key West cottage full of charm and historic features. It has a 4-bedroom and 3-bathroom setup, with a great room opening to the pool and patio. Outdoor amenities include a private heated pool and cabana with a deck space for sunbathing and a propane grill for outdoor cooking. The covered pool cabana is adorned with lounge chairs and sofa that’s perfect to relax in during quiet afternoons or for a cocktail party.

Click here for more info on this VRBO.

Pete’s Twin 4-bedroom Cottages with Pool – Key West

Pete’s Twin Cottages is a warm and welcoming 4-bedroom, 2-bathroom property. It’s been renovated to include a beautiful natural cypress exterior that complements its contemporary design. Each cottage opens up to a semi-private deck and lounge that’s a few steps to the large kidney-shaped pool with a waterfall. The property can be rented separately; either a 2-bedroom, 1-bathroom set up or the whole cottage.

Click here for more info on this VRBO.

Townhomes

The “Smiling Ibis” 3-bedroom Townhome with Private Pool – Key West

The Smiling Ibis is a whole mood and welcomes guests with its bright tropical colors, tall ceilings, and luxury furnishings. It has a 3-bedroom, 4-bathroom setup and plenty of space to stretch out and relax in. The private pool is fully fenced and is surrounded by tropical greenery. Guests can dine in the backyard furnished with an outdoor dining set and propane grill for barbecuing.

Click here for more info on this VRBO in the Florida Keys.

Villas

Gorgeous Waterfront 6-bedroom Villa with Pool and Boat Dock – Marathon

A highly sought-after 6-bedroom, 5-bathroom villa on Sombrero Beach. This spacious waterfront property has a heated pool and jacuzzi, a boat dock, and a spa. It’s the perfect home base for those keen on experiencing the best watersports in the Florida Keys. There’s also a 65 ft. deep water dock for private boats and a catamaran for rent should guests want to go fishing or boating.

Click here for more info on this VRBO.

Timeless 7-bedroom Victorian Villa – Key West

A piece of architectural history located in the Historic Seaport of Old Town of Key West. This 7-bedroom, 6-bathroom villa exudes elegant Victorian charm seen in its elaborate gingerbread trims, deep porches with columns, elegant stained-glass windows, and French doors. The luxurious kitchen leads to the private pool and pied-a-terre to complete living in the tropical fantasy experience.

Click here for more info on this VRBO.

Three-story Premium Waterfront Villa with Pool and Jacuzzi – Islamorada

An alluring three-story villa nestled on 4067 square feet of beachfront property. This natural haven has a 4-bedroom, 5-bathroom setup with picturesque views of Islamorada waters. It has a full kitchen as well as living and dining spaces and three outdoor waterfront lounges. Families and large groups can spend quality time and enjoy on-site amenities like outdoor fitness, watersports, and spa services.

Click here for more info on this VRBO.

Which of these VRBOs in the Florida Keys is your favorite? Let me know in the comments!

Need a house sitter while you are gone?

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It’s a fantastic way to find trustworthy people to watch your home and pets while you are away. (And on the flip side, it’s a cool way to stay in different areas of the country and world without having to pay for accommodation! I have a friend who literally didn’t own or rent a home for years, and only used TrustedHouseSitters to find the next spot she was going to stay.)