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Naples Holiday Homes

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    Travellers to Naples are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    19 Matching Rentals in NaplesView all 1,045 rentals
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    White Sands in Old Naples1 / 9
    (8)Excellent
    Old Naples
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Luxurious Olde Naples Beach House1 / 30
    (10)Excellent
    Old Naples
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Old Naples
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Old Naples Luxury Cottage - Walk to 5th & Beach !1 / 32
    (11)Very good
    Old Naples
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Our first family vacation in many years was made even more lovely having booked this house! Spacious and inviting inside, a pool just perfect in size right outside. We cannot...
    Reviewed 12 August 2017
    Enjoyed staying here - everything was as described, particularly happy with the air con in every room, the warm pool, the kitchen with everything you need and the short walk to...
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    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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 BR 3 BA Oasis, perfect location in Olde Naples1 / 22
    (9)Excellent
    Old Naples
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/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...
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    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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lovely Condo Lovely View - Quail Run Golf Course1 / 42
    (13)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Parking
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2016
    As soon as we checked in, we knew that it was going to be a great 2 months. The condo was perfect and everybody was so helpful. We liked it so much, we are now Florida residents
    Reviewed 23 April 2016
    I retired in February of 2016 and found this great condo on Trip Advisor. This place has everything that you will ever need in Naples. The condo is in excellent condition, the...
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    About this property
    Upon entering our spacious condominium nestled in the quiet golf community of Naples, Florida, the view of the lush vegetation, the golf course, and the placid lake sooths you. Sliding glass doors line the adjacent living room, dining room and kitchen, of this 3 bedroom 2 bath unit of more than...
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    Location Information
    Naples, Southwest Gulf Coast 34105
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful condo is in the heart of Old Naples close to shopping, restaurants, galleries, entertainment and the beach! The decor is done in earth tones with the living room offering a large Sony TV, DVD and VCR and queen sofa bed. The kitchen is wll equipped, has granite counter tops and 6 bar...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Fifth Avenue Beach Club 1021 / 14
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2013
    This condo is very nice and has everything you need for vacation. The updates make it extra nice, especially the new flat screen tvs in every room. The condo is within easy...
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    About this property
    LOCATION – LOCATION – LOCATION!!! This condo is perfectly situated in historic downtown “OLD NAPLES”, one and half blocks to the beach, a leisurely stroll to fine shopping, and a short walk to world class dining. This property recently underwent a FULL renovation including a new stainless steel...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kensington Gardens1 / 5
    (1)Excellent
    Old Naples
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    North Naples
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Waterfront
    • Washer
    • Cable/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...
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    Location Information
    Naples, Southwest Gulf Coast 34108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    House in Olde Naples1 / 43
    (1)Excellent
    Old Naples
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Parking
    • Cable/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...
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    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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Conway House1 / 26
    (15)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Cable/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...
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    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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    LUXURY RENTALS ~ NAPLES MERMAID COTTAGE ~ Private Beach!1 / 51
    (7)Excellent
    Moorings
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2016
    The Mermaid cottage was perfect for our group. Large and Spacious and located in the heart of Naples close to everything. Private beach really makes the experience complete!
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    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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Beach House!  4 Br, few blocks to BEACH at Vanderbilt Bch1 / 13
    (3)Excellent
    North Naples
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2017
    Home way from home. Everything that we needed and more were all here.specially fir my 3 yr old. You guys thought of everything! My birthday was fabulous everything is central...
    Reviewed 22 June 2017
    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...
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    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,...
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    Location Information
    Naples, Southwest Gulf Coast 34108
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Old Naples
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Old Naples
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Cable/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'...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Old Naples
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Expansive updated first floor end unit residence located in an intimate complex of just eight condominiums right in the heart of Olde Naples! Light Florida style decor with hints of color throughout. Immaculate condition and well maintained with recent updates including a remodeled kitchen with...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Old Naples
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Cable/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...
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    Location Information
    Naples, Southwest Gulf Coast 34102
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Waterfront
    • Cable/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...
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    Location Information
    Naples, Southwest Gulf Coast 34104
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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