We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Old Naples Holiday Rentals in Naples

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Clear all filters
    View Map
    Price
    per night
    $336 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Naples are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in NaplesView all 762 rentals
    Sort by:
    Default
    White Sands in Old Naples1 / 9
    (7)Excellent
    Old Naples
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Lovely Condo Lovely View - Quail Run Golf Course1 / 42
    (13)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Old Naples Luxury Cottage - Walk to 5th & Beach !1 / 96
    (9)Very good
    Old Naples
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Luxurious Olde Naples Beach House1 / 30
    (10)Excellent
    Old Naples
    4 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2017
    Our 3rd visit to this beautiful house reminded us why we keep coming back. The location is amazing with the beach across the road, as well as the gorgeous shops and restaurants...
    Reviewed 4 May 2016
    We look forward to our trip to the Naples Beach House each year. The house has everything we need - from the fully stocked kitchen to the vast amount of beach gear - everything...
    See all reviews
    About this property
    This casually elegant 3700 sq. ft. 4 bedroom home is located in the upscale neighborhood of Olde Naples. Located just steps away from one of Naples most pristine beaches and the Naples Pier. Charmingly designed, this home boasts 25 foot ceilings and lavish windows which provide for an open and...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
    Make Enquiry
    North Naples
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Waterfront
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WATERFRONT-SOUTHERN EXPOSURE-GULF ACCESS - Vanderbilt Beach voted #5 in US News' Most Relaxing Beaches for 2011. Voted #2 in Coastal Living's Happiest SeasideTowns. TripAdvisor's Travelers' Choice 2011 Awards Top 25 Beaches in US. THIS SUN FILLED HOME WAS RENOVATED IN DECEMBER 2009. A new...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Conway House1 / 26
    (15)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Satellite TV
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2017
    A brilliant house design allowing sunlight to pour in from all sides surrounding the stunning lanai and pool. The rooms are spacious and beautifully decorated. Both master and...
    Reviewed 2 February 2016
    My wife and I stayed at Conway House from early December 15 to Mid January 2016-during which time out daughter, partner and 2 grand-children joined us for 2 weeks.The house was...
    See all reviews
    About this property
    Conway House is a fantastic family holiday home situated in a private location in old Naples. Whilst the house is central (only 5 mins drive to the beach and to the Coastland shopping centre) it is in a very quiet residential area and backs onto a lagoon. The villa is single story and is very...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Waterfront
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BRIARWOOD villa, yet another beautiful, well kept home in the heart of Naples offers both superb accommodation, great south facing views, privacy, security and close proximity to heart of Old Naples. This spacious 4 bed 3 bath home is within the community of Briarwood , an extremely popular gated...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34104
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    House in Olde Naples1 / 17
    (1)Excellent
    Old Naples
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2016
    I stayed in Casa Piñata in late May and very much enjoyed the wonderful home in downtown Naples. It's just a block to the beach and is close to 5th Avenue and 3rd. The house is...
    See all reviews
    About this property
    This 3 bedroom/3 bath home is nestled in Olde Naples, on a quiet street, lined with beautiful trees and just 3.5 blocks to Naples' pristine, white sandy beaches, and magnificent sunsets. The living room is decorated in cream couch/loveseat with blue trim, and chair. The family room is decorated...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 BR 3 BA Oasis, perfect location in Olde Naples1 / 22
    (9)Excellent
    Old Naples
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Shared Garden
    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2016
    This lovely private home is ideally located close to the beach (a 5-10 minute walk) and also close to restaurants and shopping in downtown Olde Naples. The interior of the house...
    Reviewed 3 April 2014
    We just completed our second two month stay at Casa Piña and were set for next year, but unexpectedly bought a place of our own in Naples.This is a wonderful bright and...
    See all reviews
    About this property
    Location, location, location!!! This professionally managed 3 bedroom, 3 bath property in a spacious, lush and private garden is nestled in the heart of Olde Naples. The property is on a quiet street, lined with beautiful trees and just 3.5 blocks to Naples' pristine, white, sandy beaches as well...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Old Naples
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location… Location.. Location, Old Naples best Vacation Destination. This newly renovated condominium is a cozy retreat in the very heart of Old Naples. Just ½ block from Fifth Avenue South where you will find fine restaurants, live theatre, browse the array of wonderful art galleries and world...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Old Naples
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 3 bedroom, 3 bath, pool home, with wonderful Spanish tile throughout, all new furniture, and new carpet in the bedrooms. This home is just 3 blocks to the lovely, white sand beach and the Gulf of Mexico. This charming Olde Naples home is a classic. Do not let its "Beach House"...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Beach House!  4 Br, few blocks to BEACH at Vanderbilt Bch1 / 26
    (2)Excellent
    North Naples
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Washer
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I've rented many, many houses while on vacation. This was by far the best. The house is close to everything! Just a quick 30 min drive from the Fort Myers airport. The beds...
    Reviewed 11 December 2015
    This was our 2nd trip to Rob's and Karen's vacation home name Casa Playa, this time we had twin toddlers and we found the house even more better the last time, barrier to the...
    See all reviews
    About this property
    Your family will have a great vacation in our beautiful two-story 3000 sq ft, 4 bedroom 3.5 bath home that's just one mile from the beach at Vanderbilt Beach. You'll be close to beautiful Delnor Wiggins Beach Park with its famous white sand beach and blue-green water. There is ample parking,...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34108
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Old Naples
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This completely remodeled, 2 bedroom, 2 bath (sleeps six) "Cape Cod" cottage-style home is just steps from the beach! This home offers a living area with gas-burning fireplace, all new furniture, with over-stuffed blue couch, two white over-stuffed chairs, with floral cushions, a white chintz...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Old Naples
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magnificent Beachfront home located in Olde Naples. This Four Bedroom, Four Bath home with a one Bedroom/one Bath/Living Room/Kitchen "Guest House", has been newly constructed in 2001. Each bedroom gives one the feeling of a private suite. It's simplicity of design and the way the home merges with...
    View all property information
    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    List your property
    Owner log in