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.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $320 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Selected
    Sleeps
    Any
    View Map
    More filters
    loading...
    Applied filters:
    Old Naples
    Clear All
    1 / 19
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 41
    4.5 of 5 stars (12) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 9
    5 of 5 stars (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Waterfront
    • Satellite TV
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • 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
    1 / 26
    5 of 5 stars (14) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Satellite TV
    • Secure Parking
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 stars 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...
    5 of 5 stars Reviewed 15 November 2013
    We stayed for one week in November at Conway House with two young children. Everyone agreed that this was the best trip ever! The house is absolutely immaculate with every...
    See all reviews
    1 / 22
    5 of 5 stars (8) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Shared Garden
    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    5 of 5 stars 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...
    5 of 5 stars Reviewed 3 February 2012
    We were pleasantly surprised by this rental. The house is clean and functional and the pool was really nice for our teenagers. Everything worked well and the kitchen was well...
    See all reviews
    1 / 30
    5 of 5 stars (9) Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    5 of 5 stars 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...
    4 of 5 stars Reviewed 20 May 2014
    Our family spent 4 days in this house while attending a wedding. We have been to Naples many times, but had never rented a house. It was perfect for our group. The location...
    See all reviews
    1 / 5
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A terrific Old Naples vacation destination. This newly built condominium community is a cozy retreat in the very heart of Old Naples. Walk to the beach, fine restaurants and live theater, browse the array of art galleries and world class shopping, from this cozy residence. This property is... View all property information
    Location Information
    Naples, Southwest Gulf Coast
    5 of 5 stars Reviewed 9 February 2015
    This small condo complex is smartly updated, very clean, well maintained and in the PERFECT location!! It is amply appointed to fill all needs and is only 1/2 block from the...
    See all reviews
    1 / 9
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Washer
    • Satellite TV
    • Patio
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful two-story 4 bedroom 3.5 bath home just one mile from the beach at Vanderbilt Beach. Close to Delnor Wiggins Beach Park and a parking pass to the beach park is provided. Excellent location for shopping and restaurants. Trader Joe's less than a mile. Whole Foods about 1.5 mi. A great... View all property information
    Location Information
    Naples, Southwest Gulf Coast
    5 of 5 stars 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
    1 / 32
    5 of 5 stars (7) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    "Chatterbox Cottage" in the Heart of Olde Naples - Ideal Location! Can walk to beach and restaurants Sophisticated unique luxurious four bedroom, two bath Cottage with heated swimming pool in the Historic District of Olde Naples on quiet street just a short 2 block walk to prestigious Fifth... View all property information
    Location Information
    Naples, Southwest Gulf Coast
    5 of 5 stars Reviewed 12 April 2016
    Great location to beach and to the restaurants and shops on 5th and 3rd. We didn't have to get in the car to go anywhere once we arrived. Clean and very attractive home...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 51
    5 of 5 stars (6) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Naples' best vacation home! Luxury Old Florida Beach House style pool home in heart of Old Naples prestigious Moorings. Lushly landscaped tropical pool area. Features one of the few private beaches in Naples. This home has been beautifully furnished by one of the countries top designers. No detail... View all property information
    Location Information
    Naples, Southwest Gulf Coast