Browse 400 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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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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Located on Vanderbilt Bay this lovely 4th floor condo just 500 steps to the beach appears surreal as its charm and elegance inspire you for costal life-on-the-bay!
Experience timeless elegance in the prestigious, gated enclave of Hemingway Place.
Welcome to 315 Dunes Blvd, Unit 201 – a beautifully furnished, turnkey residence located in the premier resort-style community of The Dunes of Naples.
Life is Good at The REGATTA! One Block to Naples Pristine Beach with a Great View! Naples Florida is ranked among the Top 10 Florida vacation destinations by US NEWS & WORLD REPORT!
Welcome to one of Olde Naples' most sought-after addresses — a beautifully renovated three-bedroom, three-bath single family home offering the quintessential Naples lifestyle in a setting of privacy, …
Luxury Waterfront Vacation Home in Park Shore available from April 2026 and the entire 2026/2027 winter season.
Light, fresh and airy...this beautiful beachfront condo is more charming than ever. The lovely palette of neutrals and light tones will awaken your senses.
This luxurious penthouse is the perfect vacation rental in the heart of Old Naples, FL. Ideal for those seeking a high-end getaway, this property offers everything you need for a memorable stay.
Welcome to your oasis of tranquility in the heart of Naples, FL! Nestled in the prestigious community of Carlton Lakes, this spacious 3-bedroom, 2-bathroom home beckons with its serene ambiance and prime location.
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.
The CARLYSLE at BAY COLONY 15th floor home in the sky has spectacular views including sunrises over Naples and sunsets over the Gulf of Mexico!
This beautifully decorated two-bedroom condo is steps from the beautiful sand and surf of Vanderbilt Beach and Delnor Wiggins State Park. This 4th floor corner residence has lovely Bay and Gulf views.
Transferable Golf Membership! 30-day minimum bookings. Available October-December 2026 and May-December 2027.
Gorgeous garden and fountain views from this third floor 3 bedroom 2 bath Valencia condominium.
Discover the ultimate vacation retreat in this 3BR+open den/2.5BA condo at Regatta at Vanderbilt Beach.
After catching the tram outside your back door for a day at the beach or spending a relaxing afternoon at the pool, you will feel right at home upon returning to this comfortably furnished 2nd floor 2…
Discover an elevated seasonal rental experience in this beautifully renovated 2-bedroom, 2-bath condo in Harbourside Gardens, one of Naples' most desirable bayfront communities in The Moorings.
Located in prestigious Park Shore with nearby private beach access, this newly constructed masterpiece by PGI Homes and furnished by Robb & Stucky is a single-family residence designed for refined coastal living.
WELCOME TO YOUR PERFECT PLACE IN THE SUN!
Bolero at Tiburon is a private gated enclave of only 60 condo homes with its very own resort style pool, hot tub, and grills. This 2nd floor unit is the ultimate in luxury living.
Loving Lely Resort! You will love the panoramic views of the lake and Mustang Golf Course from the large screened lanai. Highly desirable first floor 3 bedroom turnkey furnished condominium.
This beautiful new listing in Vanderbilt Towers at 5 Bluebill Ave. is available for season and off-season as well. Come make this your vacation destination and be close to all the wonderful amenities Naples offers.
South Naples Condo-Close to Shopping and Restaurants-Community Pool and Bocce Court!
Escape to paradise in this stunning 3 bedroom, 3 bathroom terrace condo with breathtaking bay views and over 600 sq. ft.
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.
