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Old Naples Vacation Rentals

(26 rentals)
Naples Apartment
Sleeps 6, 2 bedrooms, 1 bathroom
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to the heart of beautiful, sunny Naples! Your new home away from home.This 2 bedroom, 1 bathroom apartment is centrally-located in the Downtown of Naples. Everything is within walking distance or minutes drive away. Shops, restaurants, bars, & the beach. You’ll love your time spent ...

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$118
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

RARELY AVAILABLE LOCATION!Experience the best of Naples from this stunning 2-bedroom, 3-bathroom condo located on the world-famous Fifth Avenue South. This spacious unit is in the most sought-after location in Naples, offering unparalleled access to the finest shopping, dining, and entertainment ...

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$191
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Newly remodeled condo in a small complex. Ground floor. Master Bedroom has King size bed, plenty of closet space and private bathroom. Second bedroom has Queen size bed. Both bathrooms have walk in showers. Open floor plan for kitchen, dining and living room area. Kitchen is well equipped. Screened Lanai ...

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$67
avg per night
Naples Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 0.2 miles to Old Pier Pilings

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

White Sands is an updated old Florida style resort located in the heart of Old Naples and is an easy walk to the beach, shopping and dining on Fifth Avenue. White Sands Club offers a relaxed atmosphere with a heated pool and spa tub, outdoor BBQ grills and shuffleboard with bicycles, beach umbrellas, ...

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Featured review

"Perfect Location"

The best part of this place is the location - 2 short blocks to the beach. It is clean and the grounds are very well maintained. Pool is nice and warm. A 1-bedroom is perfect for a small family with eat ...

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$161
avg per night
Naples Villa
Sleeps 6, 4 bedrooms, 3 bathrooms

Distance to beach: 0.4 miles to Gulf of Mexico Naples Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

A large Villa with a private courtyard, pool and spa. Recently remodeled with a full kitchen, master suite and three additional bedrooms. A private garage with two extra parking spaces and guest parking.Centrally located, 3 blocks from Historic 3rd St South, 5 blocks from 5th Ave South, 4 blocks from ...

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$572
avg per night

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Naples Townhome
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 50 yards to 5TH AVENUE BEACH

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

TWO BEDROOMS EACH HAVE A KING BED ,MULTIPLE DRESSERS AND AMPLE CLOSET SPACE TWO FULL BATHROOMS EACH CONTAINING A SHOWER AND TUB COMBINATION GROUND LEVEL PRIVATE OUTDOOR PATIO WITH BEAUTIFUL ORCHID GARDEN OVERLOOKING 5TH AVENUE LARGE OPEN LIVING DINING AREA LARGE FULL KITCHEN WITH A LARGE NUMBER OF ...

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Featured review

"Sun dial"

Very nice, spacious condo, as advertised. Excellent position near to the beach and restaurants. Perfect for a couple. Randy and Amy were great hosts, very helpful, an easy check in. Would highly recommend. ...

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$250
avg per night
Naples Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 1 miles to little over a mile

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

NEWLY RENOVATED 1 STORY END UNIT NEAR NAPLES BAY RESORT WITH A DOCK TO ENJOY THE WATERFRONT BOATS & BIRDLIFE. THERE ARE 2 BEDROOMS EACH HAS ITS OWN BATH. MASTER HAS NEW KING BED AND 2ND HAS NEW QUEEN BED. FLAT SCREEN TVs IN BOTH BEDR0OMS AND A 75" TV WITH FREE THE MAIN OPEN FLOOR PLAN AREA. ...

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Featured review

"1595 Curlew Stay"

Our stay at Elina and Sami's place has been delightful. They thoughtfully stocked the kitchen, tastefully decorated the condo, and provided exceptionally comfortable beds. Having a puzzle table was a wonderful ...

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$167
avg per night
Naples House
Sleeps 10, 5 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Listed rate is for High Season (Nov. through April). Longer High Season leases have greater discounted rates. Annual Rate is $40,500 per month. Located only two blocks to the beach and featuring lush, mature tropical foliage, this classic Bermuda styled home offers absolutely stunning interiors. The sprawling ...

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$1,452
avg per night
Naples House
Sleeps 10, 5 bedrooms, 5 bathrooms

About this property

This finely decorated home is the pinnacle of luxury Old Naples living. The Balmoral has five bedrooms and plenty of living space, with tall ceilings and large windows for tons of light. The open living room and kitchen layout overlooks sliding glass doors that lead directly to the pool. The pool area ...

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$1,129
avg per night
Naples House
Sleeps 14, 7 bedrooms, 4 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

6 bedrooms; 4 full bathrooms; sleeps 14 Luxury home in desirable Old Naples. Nestled in the heart of Old Naples, 75 yards to the beach 2 blocks from shopping / restaurants (Fifth Ave South / Third Street), this professionally decorated private oasis is the perfect setting for your family or corporate ...

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Featured review

"Beautiful home!"

We had all the comforts of home & the pristine beach just seconds away. We had beautiful accommodations & everything we needed. Our family had a wonderful vacation with plenty of space for our group of ...

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$1,714
avg per night
Special Offer
Naples House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Never miss a sunset from this beautifully appointed beach house, located just steps from Naples Famous Pier and beautiful white sand beaches, this home's location can't be beat! A luxurious luxury home with all the bells and whistles. Enjoy sunsets from the rooftop deck or stroll down to the ...

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$1,129
avg per night
Special Offer
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to the Cypress House!Professionally decorated 3 bedroom and 2.5 bathroom home in the heart of Old Naples. The Cypress is on a quiet mahogany tree-lined street just a short walk to the beautiful beaches and refreshing waters of the Gulf of Mexico as well as popular dining, shopping, and the ...

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$557
avg per night
Naples House
Sleeps 12, 6 bedrooms, 7.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Open & bright, loaded w/upgrades! Absolutely ...

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$1,271
avg per night
Naples House
Sleeps 10, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Featured in Naples coffee table books "Dream Homes" FLAMINGO PALMS is one of Olde Naples finest homes superbly located in the heart of Olde Naples historic district. Walk to some of Naples finest restaurants and shopping along Olde Naples Famous Fifth Avenue, Just 2 blocks away. Enjoy a round ...

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$800
avg per night
Naples House
Sleeps 9, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Look out your window to see a stunning view of the Gulf, have breakfast, enjoy the beach or a stroll down the Naples Pier. The Pier at night is amazing--enjoy a 360 degree view of the ocean under the stars or come home to relax on the rooftop deck and enjoy the night sky.The Pier House is stunning ...

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$986
avg per night
Naples Cottage
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Enjoy sunny Old Naples at reasonable rates, 75 yards to the beautiful beaches of Old Naples at a charming guest house efficiency on an estate property. This property is located in the heart of the most exclusive section of of Old Naples, steps to the Gulf of Mexico and the fine shops of Fifth Ave and ...

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$133
avg per night
Naples House
Sleeps 10, 5 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Wonderful & well-built in 2007! Open & bright, ...

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$1,357
avg per night
Special Offer
Naples House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Coconut Plantation is the pinnacle of Naples luxury living. Prepared to be enchanted upon arrival as you are greeted by a lush landscape. Royal Poinciana frame this plantation style house that overflows with southern charm. A brick paver circular driveway provides the gateway to this southern style ...

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$1,414
avg per night
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to The Cambier Cottage, a charming vacation home nestled in the heart of Olde Naples, Florida. This delightful retreat seamlessly combines comfort, convenience, and artistic flair. Expertly handcrafted by a talented local Naples artist, every corner of this three-bedroom, three-bathroom haven ...

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Naples House
Sleeps 10, 5 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your own slice of paradise in Naples, Florida. Nestled in a prime location, just 5 blocks away from the vibrant 5th Avenue shops and restaurants, and a mere 2 blocks from the sun-kissed beach, this opulent 3-story estate is a dream come true. With 6 spacious bedrooms, this residence exudes ...

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$843
avg per night
Naples House
Sleeps 9, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Relax with the whole family in this 5 bedroom home featuring pool, spa, outdoor shower, bikes and newer gourmet kitchen.In additional to a large open living room, there is a den with large TV. Higher end furnishings from restoration,West Elm . The dining area indoor and outdoor accommodates ...

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Naples Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 0.9 miles to Naples Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This spacious 2-Bedroom Suite includes a king-size bed in the primary bedroom, two twin beds in the secondary bedroom, a sleeper sofa in the living area, a screened lanai and a kitchen. Fully-equipped kitchens include a coffee maker, refrigerator, oven, microwave, stovetop and toaster. Each Suite also ...

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Naples Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

!!! Available for Season 2025 !!!! Enjoy staying in charming Olde Naples. This delightful 2 bedroom condo is an easy walk to great dining and shopping on 5th Ave S and a 10 minute walk to the white sandy beach of Naples. . Both bathrooms have been updated with cabinets and counters and there is a newer ...

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Naples Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 Bedroom, 1.5 bath condo on 2nd floor. Walk in shower, bedroom 1 has queen bed, bedroom 2 has 2 twin beds. Living room has 50” smart TV with Wi-Fi included. Fully equipped kitchen with granite countertops. Screened lania with table and chairs. Assigned parking spot near stairs, also has quest parking. ...

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$133
avg per night
Naples Condo
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

THIS BEAUTIFUL ONE BEDROOM CONDO IS A FIRST FLOOR UNIT WITH COVERED PARKING. THIS CONDO WAS RECENTLY RENOVATED AND HAS NEW OPEN FLOOR PLAN WITH DINING AREA, LIVING AREA AND KITCHEN WITH BAR AREA. A 75 INCH SAMSUNG TV WITH COMCAST SERVICE AND INTERNETNCLUDED.THIS KITCHEN IS FULLY STOCKED WITH DISHES, GLASSES ...

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Naples Condo
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 30 yards to Naples beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

SPECIAL PRICE FOR OFF-SEASON MONTHS. Off season months, ONLY $199 PER NIGHT FOR MONTH of JUNE, JULY, AUGUST, SEPTEMBER !!! CONTACT OWNER FOR DETAILS AND AVAILABLE DATES! Book now only $199 per night. Great location in Olde Naples walk to 5TH Ave and to Naples Beach!!! Minimum stay 5 days. Reserve ...

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$245
avg per night
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