Holiday Homes in South Naples

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Next weekend
15 Aug - 17 Aug
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5 Sept - 7 Sept
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Featured Holiday Homes in South Naples

3Bedroom 2.5 bath townhome in beautiful Naples Florida :
Pool

3Bedroom 2.5 bath townhome in beautiful Naples Florida :

3Bedroom 2.5 bath townhome in beautiful Naples Florida :
Gorgeous Lely Resort pool home<br>
Relax by the resort's circular pool surrounded by lounge chairs and tropical plants.

Gorgeous Lely Resort pool home<br>

10.0 out of 10, Exceptional, (2)
"Excellent"
Gorgeous Lely Resort pool home<br>
LELY Resort Gated Naples Pool Home Naples with Players Club Membership
Relax by the pool surrounded by a scenic view.

LELY Resort Gated Naples Pool Home Naples with Players Club Membership

LELY Resort Gated Naples Pool Home Naples with Players Club Membership
Deluxe home in a resort community with amazing views, pool, & hot tub
Laundry room with a front-loading washing machine, a tiled backsplash, and a shelf for essentials.

Deluxe home in a resort community with amazing views, pool, & hot tub

10.0 out of 10, Exceptional, (5)
"Absolutely wonderful in every way!!! "
Deluxe home in a resort community with amazing views, pool, & hot tub
Villa on golf course with heated saltwater pool.
Relax in a pool area surrounded by a patio and seating area with a thatched umbrella.

Villa on golf course with heated saltwater pool.

10.0 out of 10, Exceptional, (108)
"We enjoyed our stay in your home. "
Villa on golf course with heated saltwater pool.
Tropical Oasis- Private Heated Pool-Fire Pit-Tiki Bar-Large Yard-Great Location!
Relax by the serene pool surrounded by lush greenery and palm trees.

Tropical Oasis- Private Heated Pool-Fire Pit-Tiki Bar-Large Yard-Great Location!

10.0 out of 10, Exceptional, (4)
"Loved the home and pool. All remodeled and well cared for. Grandkids visited for few days and it worked out perfectly! "
Tropical Oasis- Private Heated Pool-Fire Pit-Tiki Bar-Large Yard-Great Location!
Naples Duplex Home w/ Private Pool & Lanai!
Features a sleek kitchen with stainless steel appliances, white cabinetry, and an oven hood.

Naples Duplex Home w/ Private Pool & Lanai!

10.0 out of 10, Exceptional, (12)
"Beautiful home so nice and clean!! Hosts were wonderful and extremely nice and accommodating!!"
Naples Duplex Home w/ Private Pool & Lanai!
Cozy 3 bedroom with private pool and lakeview
Swim surrounded by lush greenery and palm trees with a clear view of the water.

Cozy 3 bedroom with private pool and lakeview

9.8 out of 10, Exceptional, (13)
"We had a wonderful time in this beautifully decorated cozy house with a great pool, Our grandkids stayed with us for five days and had a blast! Bikes and beach equipment in the garage was very convenient. Beds were very comfortable and kitchen had everything we needed. Host was great and very easy to reach if we had any questions. Would definitely stay here again!"
Cozy 3 bedroom with private pool and lakeview
2025 Season Still Available 3 BED.3BATH GOLF POOL HOME IN TREVISO BAY
Relax by the pool surrounded by palm trees and lounge chairs, with a waterfall feature in the background.

2025 Season Still Available 3 BED.3BATH GOLF POOL HOME IN TREVISO BAY

10.0 out of 10, Exceptional, (11)
"We had a great stay at Treviso Bay and everything was great. Highly recommend. Naples isn't for everyone as its pricey and gated communities have their fair share of rules but for my family and my dogs it was perfect and great to get away from the snow and cold of Chicago. Gabrial was great as well super responsive.... the house was as advertised. In retrospect I wish the 3rd bedroom had a queen-sized bed instead of a trundle bed but that is personal choice and my family need."
2025 Season Still Available 3 BED.3BATH GOLF POOL HOME IN TREVISO BAY
2025 Season Available ! TREVISO BAY - RESORT. LUXURY POOL & Spa GOLF HOME
Relax by the serene pool, surrounded by lounge chairs and umbrellas, with a gentle waterfall creating a soothing ambiance.

2025 Season Available ! TREVISO BAY - RESORT. LUXURY POOL & Spa GOLF HOME

10.0 out of 10, Exceptional, (10)
"Great location and very convenient to everything downtown and beach. "
2025 Season Available ! TREVISO BAY - RESORT. LUXURY POOL & Spa GOLF HOME
“Just One Look!” East NAPLES family home w/pool. 5 miles to Naples beaches!
Stroll through a lush garden featuring tropical plants and a pool.

“Just One Look!” East NAPLES family home w/pool. 5 miles to Naples beaches!

10.0 out of 10, Exceptional, (2)
"Exceptional property in East Naples, close to everything. Clean, comfy beds, great linens, and a super attentive host. We were in town for a family event and this house was just perfect, plenty of room for all of us, great relaxation pool-side and in the spacious, well-appointed kitchen. TY Alona, so glad we chose your property. We will be back! "
“Just One Look!” East NAPLES family home w/pool. 5 miles to Naples beaches!
Families-private heated pool & hot tub-pickle ball,
Enjoy cooking in this well-lit kitchen with a large island, stainless steel appliances, and ample cabinetry.

Families-private heated pool & hot tub-pickle ball,

Families-private heated pool & hot tub-pickle ball,
Newly remodeled pool home with PLAYERS CLUB access in Lely Resort!
Relax in this serene space with a view of the pool and lush greenery, featuring a comfortable sofa and flat-screen TV.

Newly remodeled pool home with PLAYERS CLUB access in Lely Resort!

10.0 out of 10, Exceptional, (7)
"Great property, open floor plan makes for ideal family gatherings. Would definitely recommend and stay agin in the future!"
Newly remodeled pool home with PLAYERS CLUB access in Lely Resort!
PICCADILLY MANOR-3BD/2BA W HEATED POOL +1 773 443-7832
Enjoy a meal at the dining table surrounded by a view of the outdoor pool.

PICCADILLY MANOR-3BD/2BA W HEATED POOL +1 773 443-7832

10.0 out of 10, Exceptional, (10)
"Great layout. Loved the outdoor space. Excellent communication."
PICCADILLY MANOR-3BD/2BA W HEATED POOL +1 773 443-7832
Lakefront Naples Lely Resort, 3BR Heated Pool + Players Club & Spa Access Option
Outdoor pool, a heated pool

Lakefront Naples Lely Resort, 3BR Heated Pool + Players Club & Spa Access Option

10.0 out of 10, Exceptional, (6)
"great location"
Lakefront Naples Lely Resort, 3BR Heated Pool + Players Club & Spa Access Option
Beautiful house in Lely Golf Estate area in Naples, Florida, USA
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and island with bar stools.

Beautiful house in Lely Golf Estate area in Naples, Florida, USA

9.6 out of 10, Exceptional, (20)
"beautiful place, friendly manager, great introduction, convenient and safe location, nice layout, sizable heated pool is the highlight."
Beautiful house in Lely Golf Estate area in Naples, Florida, USA
Experience the irresistible charm of Cayo Coco Cottage!
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, double oven, and coffee maker.

Experience the irresistible charm of Cayo Coco Cottage!

2.0 star property
Experience the irresistible charm of Cayo Coco Cottage!
Beautiful Home with Pool on Golf Course in Lely
Relax by the resort's central pool, surrounded by palm trees and lounge areas.

Beautiful Home with Pool on Golf Course in Lely

10.0 out of 10, Exceptional, (1)
"Gorgeous property on the Classics Golf Club 11TH hole Pool and hot tub Great BBQ Walking distance to the Classics GC Giant TV to watch the Masters Golf Tournament Suggestion- leave directions for hot tub on kitchen counter-top"
Beautiful Home with Pool on Golf Course in Lely
New Listing - Private 3 bed, 2 bath home with large, fenced in backyard
Enjoy a comfortable living space with a central kitchen island, sofa, flat-screen TV, dining table, and ceiling fans.

New Listing - Private 3 bed, 2 bath home with large, fenced in backyard

10.0 out of 10, Exceptional, (14)
"Everything about this place was perfect!!!"
New Listing - Private 3 bed, 2 bath home with large, fenced in backyard
Beautiful Updated Home, Private Pool, Minutes from Downtown 5th Ave & Beaches!!!
Relax on the beachfront terrace with ocean views, shaded tables, and comfortable seating.

Beautiful Updated Home, Private Pool, Minutes from Downtown 5th Ave & Beaches!!!

10.0 out of 10, Exceptional, (41)
"This house had everything my family needed for the pool & beach. Location is about 15min from the beach and there is a Publix down the street. overall very happy with our stay here! "
Beautiful Updated Home, Private Pool, Minutes from Downtown 5th Ave & Beaches!!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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