Browse 400 vacation rental homes and condos, from Olde Naples cottages to North Naples beach condos, with live pricing from trusted local rental agencies.
Prefer a curated, bespoke stay? Many visitors work directly with an agency for tailored recommendations and concierge-level service. Meet Naples' top rental agencies →
400 condos and homes from $53 to $2,143 a nightmost in Vanderbilt Beach, Treviso Bay and Pelican Bay44 pet-friendly54 sleep 8+
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Painted Sunsets in Coquina Sands! Enjoy Gulf views from this 2-bedroom, 2-bath residence in the boutique setting of The Del Mar.
This beautifully remodeled 10th-floor, 3-bedroom/3-bath condo offers over 2,000 sq ft of luxurious waterfront living with breathtaking western views of the Gulf of Mexico and the Ritz Carlton Resort.
Welcome to this beautifully appointed waterfront residence in the highly sought-after Regatta at Vanderbilt Beach, where coastal elegance meets relaxed Naples living.
Welcome to your perfect Naples getaway in the sought-after new community of Esplanade by the Islands!
Escape to paradise at Regatta at Vanderbilt Beach! Experience serene bay vistas and breathtaking sunsets over the Gulf from your own spacious and private lanai.
This gorgeously remodeled house is the ideal fusion of your modern coastal home and your Olde Naples beach cottage.
Discover the perfect coastal escape at this beautiful 3BR/2BA retreat, located on the bay and just a short stroll from Vanderbilt Beach. This well-appointed condo has everything you need for a comfortable stay.
Welcome to Kalea Bay, an epitome of luxury living in North Naples, Florida.
Welcome to your Naples getaway in the highly desirable gated community of Wilshire Lakes.
Available for the 2027 Season! Spend your winter in the heart of Old Naples, where beach days, memorable dining, and relaxed coastal living are all just moments from home.
Welcome to this beautifully redone single-family home in the heart of Naples—available as a seasonal rental!
Discover the ultimate vacation retreat in this charming 1-bedroom, 1-bathroom corner-unit condo, perfectly nestled in the highly sought-after Twin Palms complex.
A HIDDEN GEM IN PARK SHORE LANDINGS. 2 BD/2BA ideally positioned with spectacular western views of the Venetian Bay and close to the Village where one can dine at bay side restaurants and shop to their hearts content.
Vanderbilt Beach Area-Top Floor Condo-Walking Distance to the Beach- Gulf of Mexico Views! Enjoy magnificent views of gulf sunsets and the bay from this rarely available top floor condo.
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.
This condo is like brand new. Recently the unit was renovated with new features, brand new furniture, new plumbing, and furnishings. Bright and airy with 3 bedrooms and 2 full baths!
Lots of charm in this nature-influenced community of The Isles of Collier Preserve.
Welcome to your ideal getaway! This beautifully appointed 3-bedroom, 2-bath condo is nestled in the highly desirable Beachwalk community in Naples, FL.
Chanteclair Maisonettes at Pelican Bay is an ideal year-round vacation destination surrounded by everything one needs to enjoy Naples living.
BEAUTIFULLY UPDATED THREE BEDROOM CONDO JUST MINUTES FROM VANDERBILT BEACH: This three bedroom two bath condo located off Vanderbilt Beach Road is only a short stroll to the sandy white beaches and st…
Spectacular renovation done on this Princeton Place Pent House condo in Wiggins Bay with beautiful views.
Experience the best of Naples living in this beautifully renovated 2-bedroom, 2-bath condominium in Serendipity at Pelican Bay.
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.
Available for a seasonal rental or annual (12 consecutive months).
Renting a condo or home is one of the easiest ways to settle into Naples for a week or a whole season. Most of the area's vacation rentals are condos near the Gulf, from the towers of Vanderbilt Beach and Pelican Bay in North Naples to Park Shore and the Moorings closer to downtown, with homes and villas in communities such as Treviso Bay and Lely Resort in East Naples.
The homes here come from local rental agencies, with nightly prices from their own booking systems. You book directly with the agency, so check its minimum stay, which is often longer in winter and spring. Then plan the rest of your trip with our guides to Naples beaches and restaurants, or meet the agencies.
