Naples Vacation Rentals Homes & Condos
Browse 373 vacation rental homes and condos, from Olde Naples cottages to North Naples beach condos, with live pricing from trusted local rental agencies.
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Showing 1–24 of 373 properties
Continental Club 509
From the 5th floor of the Naples Continental Club, the Gulf of Mexico doesn't just peek through — it commands the entire view.
Wildblue
LUXURY LIVING! Nestled amongst beautiful waterfront residences in a pristine setting in WILDBLUE. This home offers plenty of natural light throughout its open layout.
Sandpiper # 79
Welcome to your laid-back Naples retreat in Royal Bay Villas—a charming, ground-floor 2BR/2BA condo designed for comfort, convenience, and that “we’re finally on vacation” feeling.Inside, you’ll find …
Vanderbilt Towers - Vanderbilt Beach - Bayside 803
Breathtaking Views of the Gulf from an expansive 8th-floor lanai, and an enviable location steps away from beaches at Delnor-Wiggins State Park are all wrapped up in this bright Vanderbilt Towers Penthouse residence.
The Mark 311
Experience upscale Naples living at The Mark on 8th, a premier condominium in the heart of Olde Naples — just steps from world-class dining, boutique shopping, and the white sand beaches of the Gulf of Mexico.
Pebble Creek in Pelican Bay 302
Available for a seasonal rental or annual (12 consecutive months).
Giaveno 1336
Step into refined coastal living with this stunning 2-bedroom, 2-bath condominium in the prestigious Treviso Bay community of Naples.
Olde Naples Marina Manor 209C
LOCATION !!! LOCATION !!! LOCATION !!! Olde Florida Style Turnkey Rental in Olde Naples. and so close to the Beach! This rare end unit featuring an abundance of windows offers plenty of natural light throughout the day.
Piacere 9419
This exceptional 3-bedroom home, located in the desirable Treviso Bay community, offers a rare chance to rent a property with a full golf membership to the exclusive TPC Treviso Bay golf course—an ame…
La Tour Rivage in the Moorings 15
Beautiful beachfront villa with unobstructed views of the sparkling Gulf of Mexico! Situated among the soon to be ultra luxury skyline that will soon be filled $15-$30 million dollar condos and the Four Seasons Resort.
Giaveno 1714
Welcome to your seasonal escape in the highly sought-after Treviso Bay community in South Naples.
Ole at Lely Resort 8207
Rarely available seasonal townhouse in the heart of Lely Resort offering the best of Southwest Florida resort living.
Acqua 234
Welcome to Acqua 234 in Treviso Bay, a comfortable 2-bedroom, 2-bath condominium in one of Naples’ most desirable gated communities.
Bayview II at Bonita Bay 602
Luxurious and gorgeous remodel! This "new to the market" rental property is ready for occupancy.
Naples Cay PH105
Sunset Gulf views from the penthouse level, a private beachfront enclave, and Waterside Shops within walking distance.
Vanderbilt Towers - Vanderbilt Beach - Bayside 610
Vanderbilt Beach Area-Marina Views-Walk to the Beach! This beautiful Naples condo overlooks the Bay and Marina. Wonderful water views from the sixth floor. Two Queen beds!
Trevi 5421
Step into luxury with this exquisite three-bedroom, two-bathroom condo nestled in the esteemed Treviso Bay, a premier resort-style community in Naples, Florida.
Furse Lakes Club E8
South Naples Condo-Close to Shopping and Restaurants-Community Pool and Bocce Court!
Naples Park 519
Stunning private Naples retreat with heated pool minutes from the beach! Cheerful 3-bedroom, 2-bath home with a bright open layout, fully equipped kitchen and relaxed coastal style.
Hemingway Place
Experience timeless elegance in the prestigious, gated enclave of Hemingway Place.
Acqua 116
This beautifully appointed first-floor condo in Acqua offers easy single-level living, a screened lanai, and — most importantly — a transferable TPC golf membership, the single hardest-to-find feature in the community.
Regatta 602
Absolutely stunning, this recently renovated 3-bedroom, 3-bathroom home is a true masterpiece.
Bluebill 606
Water on Two Sides, the Beach at the End of the StreetFrom the sixth-floor corner of Vanderbilt Surf Colony II, the view works all day: morning light on Water Turkey Bay, boats idling out toward Wiggi…
St. Nicole at Pelican Bay 304
St. Nicole at Pelican Bay is available for season, 2025! This corner third floor unit features a split floor plan with three bedrooms, two baths, a large great room, white kitchen, and a separate dining area.