Holiday rentals near Fifth Avenue South
We found 4,284 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Fifth Avenue South that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a pool. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Fifth Avenue South
Showing deals for:10 Oct - 17 Oct
Image gallery for Beautiful Vacation house in Naples - Florida Long term rental welcome
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Beautiful Vacation house in Naples - Florida Long term rental welcome
Naples, FL
8% off
Price is NZ$4,167
NZ$4,167
NZ$595 per night
includes taxes & fees
Image gallery for Private Pool and Lanai! Walking distance to Vanderbilt Beach!
1010 out of 10 rating
Exceptional
(47 reviews)
Private Pool and Lanai! Walking distance to Vanderbilt Beach!
Naples, FL
8% off
Price is NZ$4,435
NZ$4,435
NZ$634 per night
includes taxes & fees
Image gallery for Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
Naples, FL
7% off
Price is NZ$2,186
NZ$2,186
NZ$312 per night
includes taxes & fees
Image gallery for Gorgeous Pelican Bay Home w/ Private Pool, Spa & 3 Mile Private Beach!!
1010 out of 10 rating
Exceptional
(5 reviews)
Gorgeous Pelican Bay Home w/ Private Pool, Spa & 3 Mile Private Beach!!
Naples, FL
5% off
Price is NZ$18,974
NZ$18,974
NZ$2,711 per night
includes taxes & fees
Image gallery for Private Resort w/ IMAX Theater,Heated Pool,Spa! Close to Paradise Sports Complex
8.88.8 out of 10 rating
Excellent
(5 reviews)
Private Resort w/ IMAX Theater,Heated Pool,Spa! Close to Paradise Sports Complex
Naples, FL
15% off
Price is NZ$9,890
NZ$9,890
NZ$1,413 per night
includes taxes & fees
Image gallery for Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16
1010 out of 10 rating
Exceptional
(11 reviews)
Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16
Naples, FL
7% off
Price is NZ$15,245
NZ$15,245
NZ$2,178 per night
includes taxes & fees
Image gallery for Vibrant home close to best beach parks and shops backyard pool with a lake
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Vibrant home close to best beach parks and shops backyard pool with a lake
Naples, FL
8% off
Price is NZ$8,022
NZ$8,022
NZ$1,146 per night
includes taxes & fees
Image gallery for Botanical garden in the backyard! Beautiful home in great location.
1010 out of 10 rating
Exceptional
(21 reviews)
Botanical garden in the backyard! Beautiful home in great location.
Naples, FL
7% off
Price is NZ$4,558
NZ$4,558
NZ$651 per night
includes taxes & fees
Image gallery for Luxury Home, Close to the Beach and Heated Pool.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Luxury Home, Close to the Beach and Heated Pool.
Naples, Florida
8% off
Price is NZ$5,373
NZ$5,373
NZ$768 per night
includes taxes & fees
Image gallery for RARE FIND! Newly Renovated Home on Golf Course!
1010 out of 10 rating
Exceptional
(8 reviews)
RARE FIND! Newly Renovated Home on Golf Course!
Naples, FL
8% off
Price is NZ$4,802
NZ$4,802
NZ$686 per night
includes taxes & fees
Image gallery for FISHERMANS PARADISE WATERFRONT POOL HOME 2 minute drive to the beach
9.89.8 out of 10 rating
Exceptional
(6 reviews)
FISHERMANS PARADISE WATERFRONT POOL HOME 2 minute drive to the beach
Naples, FL
8% off
Price is NZ$5,774
NZ$5,774
NZ$825 per night
includes taxes & fees
Image gallery for Unit 8 - Gulfview Sunset Escape
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Unit 8 - Gulfview Sunset Escape
Naples, FL
7% off
Price is NZ$2,216
NZ$2,216
NZ$317 per night
includes taxes & fees
Image gallery for 4-BD Beach House-2 Kitchens + 2 Outdoor Areas-Downtown 5 Min-Beach/Pier 5 Min
1010 out of 10 rating
Exceptional
(5 reviews)
4-BD Beach House-2 Kitchens + 2 Outdoor Areas-Downtown 5 Min-Beach/Pier 5 Min
Naples, FL
14% off
Price is NZ$3,369
NZ$3,369
NZ$481 per night
includes taxes & fees
Image gallery for Villa Vera - Naples near to the beaches, large heated private pool
9.29.2 out of 10 rating
Wonderful
(18 reviews)
Villa Vera - Naples near to the beaches, large heated private pool
Naples, FL
10% off
Price is NZ$4,254
NZ$4,254
NZ$608 per night
includes taxes & fees
Image gallery for Beautiful Home with Guest House and Saltwater Pool-4 miles to beach
1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful Home with Guest House and Saltwater Pool-4 miles to beach
Naples, FL
8% off
Price is NZ$7,537
NZ$7,537
NZ$1,077 per night
includes taxes & fees
Image gallery for Enchanting 3BR modern house on 2.5 wooded acres in fabulous Naples. AC/WiFi/Pet.
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Enchanting 3BR modern house on 2.5 wooded acres in fabulous Naples. AC/WiFi/Pet.
Naples, FL
8% off
Price is NZ$3,949
NZ$3,949
NZ$564 per night
includes taxes & fees
Image gallery for New Listing: Charming Pool Home 1/2 mile to Lowdermilk Beach Park!
1010 out of 10 rating
Exceptional
(19 reviews)
New Listing: Charming Pool Home 1/2 mile to Lowdermilk Beach Park!
Naples, FL
8% off
Price is NZ$9,301
NZ$9,301
NZ$1,329 per night
includes taxes & fees
Image gallery for Naples Park Paradise with salt water heated pool.
9.49.4 out of 10 rating
Exceptional
(63 reviews)
Naples Park Paradise with salt water heated pool.
Naples, FL
7% off
Price is NZ$4,491
NZ$4,491
NZ$642 per night
includes taxes & fees
Image gallery for Exceptional 2 bedroom 2 bath Condo in Treviso Bay, Naples
1010 out of 10 rating
Exceptional
(12 reviews)
Exceptional 2 bedroom 2 bath Condo in Treviso Bay, Naples
Naples, FL
7% off
Price is NZ$2,242
NZ$2,242
NZ$320 per night
includes taxes & fees
Image gallery for Home with pool - walk or bike to beach!
1010 out of 10 rating
Exceptional
(12 reviews)
Home with pool - walk or bike to beach!
Naples, FL
8% off
Price is NZ$4,958
NZ$4,958
NZ$708 per night
includes taxes & fees
Image gallery for Stunning Naples home with pool, bike to the Gulf at Wiggins or Vanderbilt.
1010 out of 10 rating
Exceptional
(62 reviews)
Stunning Naples home with pool, bike to the Gulf at Wiggins or Vanderbilt.
Naples, FL
8% off
Price is NZ$5,391
NZ$5,391
NZ$770 per night
includes taxes & fees
Image gallery for Naples Retreat, Game Room + Pool, Table & Darts, Fenced Yard, Pet Friendly
1010 out of 10 rating
Exceptional
(10 reviews)
Naples Retreat, Game Room + Pool, Table & Darts, Fenced Yard, Pet Friendly
Naples, FL
7% off
Price is NZ$4,533
NZ$4,533
NZ$648 per night
includes taxes & fees
Image gallery for 4-bedroom vacation home just 10 minutes from 5th Ave. and beach.
1010 out of 10 rating
Exceptional
(18 reviews)
4-bedroom vacation home just 10 minutes from 5th Ave. and beach.
Naples, FL
7% off
Price is NZ$3,518
NZ$3,518
NZ$503 per night
includes taxes & fees
Image gallery for AMAZING South Lake View 4/3, 6 TVs, Xbox, PS5+VReal, Piano. UNIQUE Endless Pool
1010 out of 10 rating
Exceptional
(140 reviews)
AMAZING South Lake View 4/3, 6 TVs, Xbox, PS5+VReal, Piano. UNIQUE Endless Pool
Naples, FL
7% off
Price is NZ$5,390
NZ$5,390
NZ$770 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Fifth Avenue South
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Find the best place to stay - Fifth Avenue South
Downtown Naples Beach Condo, Half block from Famous 5th Ave
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Bellasera Resort
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
2,185 reviews(2,185 reviews)
A beautiful modern luxury villa
Sleeps 12 · 4 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
Sleeps 5 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
NEW POOL! Naples Home 2 miles to Beach/5th Ave, 2 King Beds, Hot Tub, Bikes
Sleeps 7 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Amazing Old Naples Location! Center of Fifth Ave & Walk to Beach
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
93 reviews(93 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value