Naples is a luxury beach destination located along the Gulf of Mexico in southwest Florida. It’s every beach vacationer’s dream getaway since most days are filled with exquisite sunsets, gorgeous beaches, and fine white sand that go for miles. This cultured city also has plenty of opportunities for world-class shopping, luxury recreation, golfing, fishing, and dolphin spotting.
Despite its glitzy reputation, Naples still has that small-town feel that you get to experience in its laidback tropical lifestyle, historic buildings, and wealth of wildlife and nature.
To help you plan your stay in Naples, we’ve found some of the best luxury VRBOs in Naples to make your stay at the Sunshine State a memorable one.
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20+ Amazing Vacation Rentals in Naples, Florida
Beautiful 5-bedroom Contemporary Waterfront Home with Cutlass Cove Views
A 5-bedroom, 7-bathroom waterfront home set in over 6,400 feet of livable space with a sophisticated and timeless design. The main suite features panoramic views of Cutlass Cove where dolphins and manatees regularly visit. You’ll find a long pool, a spa/jacuzzi, and a grill on the spacious outside deck. There’s also elevator access to the second floor where there’s an open living area with a large wrap-around couch and an 8ft billiard table.
Cozy 5-bedroom Home with Pool Near Vanderbilt Beach
This 5-bedroom, 3-bathroom home in Naples is dreamy and cozy—ideal for families or a group of friends staying for a week or more who want total privacy. It has a large screened pool and a lanai area with rattan furnishings and is close to Vanderbilt Beach and Delnor Wiggins State Park. This cozy den is also near restaurants, galleries, Mercato Mall, and La Playa Resort.
Spacious 4-bedroom Home with Gym and Newly Remodeled Pool
Located in one of Naples’s most sought-after neighborhoods is this 4-bedroom, 5-bathroom home on Moorings Street and is a short walk to Venetian Bay and downtown Naples. This spacious home has a personal gym and a well-stocked gourmet kitchen for large gatherings. The French doors open to a lovely outdoor living area decked with a heated pool with a waterfall, spa, and separate jacuzzi set in a lush tropical landscape.
Newly Redecorated 4-bedroom Home with Pool
A newly-redecorated home featuring a fresh and clean design for a relaxing stay near the beach. It has a 4-bedroom, 4-bathroom set-up, while outdoors, you’ll find a pool, lounge chairs, and a grill. The property’s excellent location on Fifth Avenue makes it accessible to the best beaches, restaurants, and Old Naples attractions.
Spacious Coastal Luxury 5-bedroom Home with Pool
A sun-filled Florida retreat awaits you in this luxury 5-bedroom home that’s a walking distance to Naples beach as well as Third Street South shopping and dining. You’ll have your own private oasis in the backyard lanai complete with a large heated swimming pool, open living rooms, chaise lounges, and a screened patio on the second floor. There’s also a private boat dock that can serve as a quiet space to relax and read.
Magnificent 5-bedroom Waterfront Home with Pool and Boat Dock
This magnificent 5-bedroom, 7-bathroom waterfront home has the perfect location to let you enjoy the Florida beach lifestyle to the fullest as it’s only a block from Third Street South and within walking distance to pristine Naples beaches. It also features an open and airy floor plan as well as a saltwater pool and spa, an outdoor kitchen, a fireplace, and a private boat dock.
Luxury 4-bedroom Home with Fenced-in Patio, Tiki Hut, and Pool
A new private home rental nestled in a quiet Country Club golfing community with four bedrooms and two bathrooms. It’s luxuriously finished with terracotta and wood flooring, as well as a fully-stocked kitchen. The wonderful outdoor set-up includes a patio with an oversized heated pool, a four-seater tiki hut, and a lanai with a dining area that seats up to eight guests.
Beautiful 5-bedroom Key West Style Home with Pool
A perfect home for a weekend getaway with family or friends, this beautiful Key West home features five bedrooms and four bathrooms that sleeps up to 12 guests. Amenities include a large screened pool with loungers, a game room with Murphy beds, and an oversized boat dock where guests can relax and launch the kayaks or paddle boards on the canals.
Mega-luxury Family Estate in Award-winning Golf Community with Large Pool
Straight out of an interior design magazine is this 5-bedroom, 4-bedroom mega-luxury family estate nestled in a private golf community surrounded by lakes and preserves. Italian-inspired furnishings with marble and modern fixtures adorn the property’s interior; while the outdoor features include an expansive heated pool with lounges overlooking a lakeshore beach. This is the place to book when you want to experience a luxury lakeside experience in Naples.
Vista Point 4-bedroom Waterfront Estate with Infinity Pool
Enjoy the balmy bay breeze and passing boats sailing on Naples Bay and the gulf in this custom-built 4-bedroom waterfront home. It comes with your very own private resort at the back deck—complete with an expansive infinity pool with a spa, a boat house dock, and a screened outdoor living area with amenities. It also comes with a concierge and management service should you wish to request more services.
Luxury 5-bedroom Sand Castle Beach House with Pool
European furnishings, natural chateau oak floors, and volume tray ceilings adorn the interiors of this luxury 5-bedroom, 5-bathroom beach house located in Old Naples in Coquina Sands. Outside is a screened lanai and a spacious heated pool with a controlled spa set in a gorgeous landscape (with surrounding fruit trees). The property is also three blocks to Lowdermilk Beach Park, galleries, restaurants, and beaches.
Gorgeous Custom-built Two-story Waterfront Home with Pool
Close to restaurants, the shopping district, and Naples Beach is this gorgeous custom-built two-story waterfront executive home with a saltwater heated pool and spa. Host dinner or barbecue parties by the pool deck with travertine marble tiles or lounge at the beautifully landscaped terrace. Another added amenity is a boat dock with direct access to the gulf and Naples Bay.
Old Naples Beach Home with Pool and Southern Exposure
This Old Naples 3-bedroom home features a southern exposure that’s warm and welcoming especially when you pass under the home’s glass walkway. The outdoor area is where it gets even better—with everything surrounded by lush landscaping and fruit-bearing trees, it’s easy to relax in the summer kitchen, dining area, the saltwater pool with spa, or on the upstairs deck to see the sunset.
5-bedroom Spring Lake Beach House with Pool
This 5-bedroom, 7-bathroom beach house is professionally decorated with a modern design to capture lakeside elegance. It features a gourmet kitchen, wide-plank wood floors, as well as an outdoor kitchen, and an infinity pool with a heated spa. Enjoy the breathtaking views of Spring Lake daily while sipping your favorite tea or coffee or relax by the firepit at night. Direct access to the Gulf of Mexico, boat rentals, and dinner cruises are also available upon request.
Charming 3-bedroom Moorings Beach House with Pool
Tastefully furnished and professionally designed by an interior designer, this 3-bedroom, 3-bathroom home is both charming and chic. You’ll have your very own beach house that comes well-equipped with five-star hotel amenities including a pool and an open living and dining area with refreshing golf course views.
Two-story Luxury Naples Home with Private Pool and Patio
This two-story home with 5500 sq ft of space has all the luxury amenities you could ever need for a comfortable stay—four bedrooms with five bathrooms for up to 11 guests, a gourmet kitchen, a spacious living room area with beach-themed decors, light fixtures, a sunny formal dining room, and a shady lanai with an expansive sun deck and infinity edge pool.
Newly Remodeled 5-bedroom Villa with Pool in Naples Park
Your key to experiencing life in coastal paradise is in this newly remodeled 5-bedroom villa which also happens to be the largest home in Naples Park. It features an authentic pizza oven and grill (for pizza nights), a great outdoor space, a heated pool with a spa, and a spacious patio to enjoy your evenings. It’s also near Vanderbilt Beach, the Ritz Carlton, and Mercado shopping area.
Stunning 4-bedroom Mediterranean Villa with Courtyard Pool
Strategically located to all Naples has to offer is this stunning 4-bedroom Mediterranean villa featuring a courtyard with a heated pool and spa, a modern chef’s kitchen, an outdoor fireplace, and a comfortable lounge area. Access to Moorings Private Beach Park as well as downtown Old Naples and Vanderbilt Beach is only minutes away from the villa.
Newly Furnished Modern Bungalow with Pool
A comfortable 4-bedroom, 3-bathroom modern cottage updated with new beach furnishings and a pool. The newly landscaped yard has over 3044 sq ft of open space for lounging. Guests will love the lanai with two dining areas that seat up to eight people and the fire pit overlooking the pool.
3-bedroom Waldorf Condominium at Moorings Beach
Experience your piece of Florida paradise at Moorings Beach in this luxury 3-bedroom, 4-bathroom condo with five-star amenities. You’ll have direct access to the building’s pool area and beach deck with loungers since the unit is located on the first floor. Visit the beach any time, relax by the fire pit right from your terrace, or explore the 2.5-mile stretch of Gulf Shore Boulevard.
Spacious 3-bedroom Condo on Vanderbilt Beach
There’s no shortage of breathtaking beach views in this 3-bedroom, 3-bathroom beachfront condo with direct access to Vanderbilt Beach. The condo has a fully-equipped kitchen and a private balcony; it also comes with access to the pristine community pool, beach chairs, and screened lanai.