Private Paradise: Luxury Vacation Home Rentals in Florida

    By Kellilynn Hann

    In the past, luxurious travel conjured images of yachts and caviar, bathroom chandeliers, staff catering to every whim, and gold-leaf everything. In a word: excess.

    However, the idea of luxury travel has evolved. Brian Chesky, Co-Founder and CEO of Airbnb, said vacationers are looking for a more holistic experience. “Today’s luxury traveler is craving more than just high-end accommodations; they seek transformation and experiences that leave them feeling more connected to each other and to their destination.”

    Carrie McDougal, President of tour company Cultural Crossroads, echoed this sentiment. “Travelers looking for a luxury trip want their dreams to become reality. They look for something unique, above their expectations… This includes exclusivity, privacy, and everything from relaxation to adventure.”

    These changing expectations means new challenges for the vacation home rental industry. A luxury vacation home needs to be more than high-end sleeping quarters. It must offer something extra — a home theater, amazing location, gourmet kitchen, concierge service — luxury travelers expect where they stay to add to the joy of the trip, to enhance their entire travel experience.

    We sorted through thousands of luxury vacation homes across Florida to bring you a selection suitable for the discerning traveler who wants (and deserves) to experience the best the Sunshine State has to offer.



    The beach is calling… and here’s your answer. Soak in the rooftop hot tub while admiring the ocean view in this modern 6-bedroom home, enjoy sand and sea vistas from all five bedrooms in this Fernandina Beach Home, or bring the whole family to this Ponte Vedra mini-mansion with elegant columned porch overlooking the beach.

    Rather be in the heart of Jacksonville’s famously vibrant city scene? Try this opulent 5400 square-foot villa, this charming home in the historic Riverside area, or this Italian-style getaway with dreamy lighted pool.

    If golf is your game, you’ll drool over this 8,300 square foot estate that backs up to the fairway of the famed TPC Sawgrass golf course.

    Experiences: Jacksonville draws thousands of sports fans every year—now it’s your turn to play. Throw a tailgate party without lifting a finger through Gameday Tailgate Experience, create a custom golf package, or head to the TIAA Bank Field for a behind-the-scenes stadium tour.

    St. Augustine

    Driftaway and Waterfront Paradise on Anastasia Island sit along the Intracoastal waterway, giving you a close-to-everything location and incredible scenery. Both homes have a private boat dock and pool.

    These properties offer the ultimate vacation luxury— your own sandy path to the beach. Try Chautauqua, a beautifully restored 1926 bungalow, Dune Walk, or this Oceanfront Premiere home with concierge service and pass to the Marsh Creek Country Club.

    Experiences: St. Augustine is the nation’s oldest city, which means plenty of interesting historical sites. Create a customized experience through St. Augustine Gold Tours, or get a double-dose of history by flying over the sights in an open-cockpit vintage biplane. To experience luxury on the water, charter a sailboat from St. Augustine Sailing or spend the day on a schooner.


    Orlando and Kissimmee

    The proximity to incredible theme parks means there’s no shortage of jaw-dropping vacation homes. Magical Vacation Homes alone has over 400 vacation homes available for rent in the area— their luxury Elite Series includes stunners like  Reunion Castle, Magical Mansion, and Grand Traverse Manor.

    Isole Villas is ideal for large groups looking to be pampered— you’ll be greeted with champagne, have an on-site spa and gym, theater, game room, saltwater pool, commercial kitchen, dining hall that seats 40, basketball court and concierge service.

    Airbnb has given their coveted Luxe ranking to several rentals near the theme parks, including Golden Bear, Muirfield London, Villa Belle, and Reunion Heights.

    Villatel not only offers incredible themed homes you’ll never want to leave, they make your stay extra fun by bringing entertainment right to you. Schedule in-home concerts, magicians, cooking classes, costume parties, art classes and much more— and capture it all with a professional photographer.

    Experiences: Did you know Disney World, Universal Studios, and Sea World offer VIP experiences? Plan your dream trip, get the best seating at shows, skip lines for rides, and enjoy behind-the-scenes access not included in regular ticket prices. 


    The large villas and rental homes common to coastal tourist areas are hard to come by here, but Gainesville has no shortage of smaller, outstanding vacation rentals. Three-bedroom homes include this Gainesville Gem near the university, this Modern Smart Home with a heated saltwater pool, and this centrally located home in the exclusive Hampton Heights area.

    Experiences: To relax and recharge, spend the day at Spa Royale, enjoy local farm-to-table dining at Mildred’s Big City Food, then finish off the evening at Blackadder Brewing Company (which has over 30 homebrew awards). If you love drag racing opt for a VIP skybox at the Gainesville Raceway.


    Cocoa Beach

    Loblolly on Merritt Island is a peaceful retreat where you can watch dolphins, sip drinks under stately oaks, and go kayaking right from the yard. Other family-friendly properties near Cocoa Beach are SailAway, Blue Horizon, and Cocoa Sands, a six-bedroom home with private beach access.

    Experiences: If you’re on the Space Coast, you must stop at Kennedy Space Center. Get a VIP view of a launch, dare to train like an astronaut, then dine with one. Also, don’t miss local favorites Ron Jon Surf Shop and Florida Key Lime Pie Company.

    Daytona Beach

    Having welcomed over 10 million visitors in 2018 alone, the Daytona Beach is clearly a desirable destination. Stay at Amarula Estates, an expansive 11-acre retreat that gives you privacy while being close to everything. You could also book this gated villa on the beach.

    Experiences: Volusia county allows bonfires on the beach, so reserve a spot and make it a magical night. If you’re a Daytona 500 fan, you’ll want to drive a NASCAR Race car around the all by yourself or as a passenger.

    Fort Pierce and Jupiter

    In Fort Pierce, you can’t go wrong with The Blue Dolphin, a secluded villa with sauna, media room, heated pool, and private beach access. Another haven of luxury and privacy is this seven-bedroom estate with the beach on one side and the Intracoastal on the other.

    For a truly one-of-a-kind experience, rent the Mansion Yacht— a, 9,000 square foot yacht-inspired home on stilts in the water.

    In Jupiter, renting the Waterway House means you can admire the turquoise waters of the inlet and the ocean, while this sleek Singer Island home offers a chef’s kitchen and grand piano.

    Experiences: If you love golf, Jupiter is the place for you. There are many courses, including the scenic Abacoa Golf Club course designed by Joe Lee and Johnathan’s Landing Golf Club with a course by Tom Fazio. If relaxing is more your speed, enjoy an amazing spa package from Jupiter Beach Resort & Spa.  


    Pensacola and Destin

    White sand beaches and clear water make Pensacola a magnet for vacationers, and rental homes here have a “wow” factor to match. Ensenada Cinco has vaulted ceilings and windows framing uninterrupted beach views, Camelot in Destin has a private pool and seasonal beach service. Smaller (but no less amazing) four-bedroom beachfront homes include Aqua Sound in Destin and El Cielo Azul, a Mediterranean-style charmer on Dune Allen Beach.

    Experiences: Pensacola is the official home of the world-famous Blue Angels. Shows are in July and November; you can watch practices starting in March. Other trip treasures: charter a private yacht, tour Navarre Beach in a Scoot Coupe, sample local citrus wine, and test your skill on the Nicklaus Course at Bay Point Golf Club.


    For a taste of country life, try Magnolia Manor, which is surrounded by ancient oaks and has an indoor pool. To be near midtown, try The Gathering at Magnolia Hill, or this luxury home that offers concierge service.

    Experiences: District 850 is the ultimate entertainment destination— dine, be a virtual reality robot, enjoy some axe throwing, try an escape room— all in one place for the luxury of maximum fun with minimum hassle. Tallahassee also has dozens of bars and nightclubs, including these swanky rooftop bars.


    Villa Adriana in North Tampa has a grand entrance that leave you speechless.

    Villa Adriana in North Tampa has a grand entrance that leave you speechless.

    - AirBnb


    Tampa and St. Petersburg

    In 2018, over 30 million people visited the Tampa Bay area. It should be no surprise, then, that luxury vacation homes abound. Try this mansion along the Hillsborough River, this Haven Beach Beauty where you can watch dolphins and yachts from the pool, Villa Adriana where the grand entrance (and every other room) will leave you speechless, or this peaceful Spa Retreat home.

    On the Gulf, enjoy the small-town beach vibes of Ocean Dreaming, (with complimentary golf cart, sea kayaks, bicycles and more) or this cheery, pet-friendly home where the beach is literally the back yard.

    Experiences: Ybor city is an historic— and wildly fun— Tampa neighborhood that’s a must-visit. Tour a cigar factory, have dinner at the famous Columbia Restaurant, then enjoy a concert at The Ritz Ybor. You can also book a VIP room at the Rock Spa & Salon and dance the night away on a Yacht Starship Cruise.

    Anna Maria Island and Siesta Key

    Anna Maria Vacations offers 95 luxury beach-front rentals that will make your vacation dreams come true. Choose from the Grand Beach House with wrap-around pool, the Banyan Tree Beach House with its breathtaking tropical grounds, or Mandalay Bay with two gourmet kitchens and rooftop deck where you can see the sunrise over the Intracoastal and sunsets over the Gulf.

    Experiences: Make good use of your gourmet kitchen by picking up fresh, locally caught fish from Island Fresh Market, ride horses on the beach and go horse surfing, or stroll through Village of the Arts to watch local artists at work and pick up one-of-a-kind souvenirs.

    Sea Oats is a nine-bedroom estate on Captiva Island with pool, tennis and basketball court, complimentary golf cart, guest house, kayaks, and concierge service.

    Sea Oats is a nine-bedroom estate on Captiva Island with pool, tennis and basketball court, complimentary golf cart, guest house, kayaks, and concierge service.

    - AirBnb


    Captiva Island, Sanibel Island and Fort Myers

    This area is a haven for nature lovers, and known worldwide for its incredible shelling beaches. Get gorgeous views of Estero Bay Preserve five-bedroom home or rent Dock Holiday and watch boats cruise along Matanzas Pass. Trident Treasure in Cape Coral lets you relax in a saltwater infinity pool while spotting dolphins on the Intracoastal waterway. Other Cape Coral homes with water access are Coral SunSet, Paradise Villa, and Tropical Escape.

    For large groups, consider Sea Oats, a nine-bedroom estate on Captiva Island with pool, tennis and basketball court, complimentary golf cart, guest house, kayaks, and concierge service.

    Sanibel Captiva Island Vacation Rentals has dozens of high-end homes, including the Suraya Beachfront Estate that feels like an Asian-inspired tropical resort, The White Ibis with bay access for fishing, Sandcastle on Captiva and Anchors Away which is designed for entertaining.

    Experiences: In addition to shelling, you can charter a deep-sea fishing trip, go on an eco-tour, rent a yacht, see the sun set over the Gulf while dining at Cōste Island Cuisine. Want something you can brag about when you return home? Take a sailing course.

    Soak up your share of the sunshine by renting Vista Point Estate, a Mediterranean-style Airbnb Luxe home on Naples Bay.

    Soak up your share of the sunshine by renting Vista Point Estate, a Mediterranean-style Airbnb Luxe home on Naples Bay.

    - AirBnb

    Naples and Marco Island

    According to a 2019 Gallup report, Naples residents enjoy the highest well-being in the United States. Soak up your share of the healing vibes by renting Vista Point Estate, a Mediterranean-style Airbnb Luxe home on Naples Bay.

    The White House in Royal Harbor is within walking distance of upscale shopping and dining. Other fantastic options are contemporary beachfront masterpiece Gulf Shore Grand, Sea Turtle Heaven, or the Caste Vanderbilt Mansion with stunning water views.

    On Marco Island, try this waterfront home, Island Estate, or Villa Bliss, an opulent 9,800 square foot home located near Roberts Bay. 

    Experiences: Spend the day playing on one of the area’s famous beaches, have a meal right on the sand at The Turtle Club, shop like a celebrity along 5th Avenue South, then wrap up your day by sailing into the sunset (literally).

    Hammock Lake Estate in Coral Gables is a sprawling country home on the lake with a fire pit, pool, and southern-style verandah.

    Hammock Lake Estate in Coral Gables is a sprawling country home on the lake with a fire pit, pool, and southern-style verandah.

    - AirBnb


    Fort Lauderdale and Miami

    If you love having lots to do but also need quiet time to relax, Fort Lauderdale is the ideal destination. Rent Villa Philippe and enjoy VIP concierge service or opt for Havana House, a soothing and private tropical oasis near the beach.

    For a taste of Miami glamour, rent one of these Airbnb Luxe rentals: The Current Penthouse with spectacular views of Biscayne Bay and downtown.

    Airbnb Luxe also has two homes in Coral Gables just south of Miami; an upscale colonial on the waterfront called Via Sunrise, and Hammock Lake Estate, a sprawling country home on the lake with a fire pit, pool, and southern-style verandah.

    Experiences: Up your chances of hanging with celebrities by taking in a show at LIV or dining at Prime 112, order VIP bottle service at E11ven Miami, or treat yourself to a private table at the famous Area 31. Of course, you’ll want to arrive in style… rent an exotic car or be chauffeured around in a limo.

    The Florida Keys

    If you want to book your own resort, Keys Luxury Hideaway in Marathon is for you. They take care of everything with stocked groceries and bar, beer on tap, kayaks and paddleboards, fitness room, games, a conference room and much more.

    In Key Largo, try Paradise Lodge, an eco-friendly estate with a main house and six cabanas, plus private beach and pier, huge pool, and entertainment room. Other top picks are this tropical oasis off the coast and historic Casa Victoria just a couple blocks away from all the fun of Old Town Key West.

    Experiences: Go diving for lobster, have a key lime pie popsicle, take a rum and reggae sunset snorkel cruise, and see dolphins in the wild from a glass-bottomed boat. If you’re a diver, you have to check out John Pennekamp Coral Reef State Park.

    Places to Remember