Holiday rentals near Fifth Avenue South
We found 4,257 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:26 Sept - 3 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$3,714
NZ$3,714
NZ$531 per night
includes taxes & fees
Image gallery for BEACH, POOL, SUNSETS in the Heart of Old Naples!
9.89.8 out of 10 rating
Exceptional
(117 reviews)
BEACH, POOL, SUNSETS in the Heart of Old Naples!
Naples, FL
8% off
Price is NZ$3,223
NZ$3,223
NZ$460 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$4,018
NZ$4,018
NZ$574 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$17,430
NZ$17,430
NZ$2,490 per night
includes taxes & fees
Image gallery for 🎄HOLIDAY SPECIAL!🎄 book 2 weeks starting in December and get 20% discount 🎉🎄🎊❄️
9.69.6 out of 10 rating
Exceptional
(5 reviews)
🎄HOLIDAY SPECIAL!🎄 book 2 weeks starting in December and get 20% discount 🎉🎄🎊❄️
Naples, FL
8% off
Price is NZ$11,053
NZ$11,053
NZ$1,579 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$1,919
NZ$1,919
NZ$274 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$8,750
NZ$8,750
NZ$1,250 per night
includes taxes & fees
Image gallery for Mini-mansion ... Downtown Where the Action is & walk to Beach
8.68.6 out of 10 rating
Excellent
(13 reviews)
Mini-mansion ... Downtown Where the Action is & walk to Beach
Naples, FL
8% off
Price is NZ$6,905
NZ$6,905
NZ$986 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$2,341
NZ$2,341
NZ$334 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$4,552
NZ$4,552
NZ$650 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$3,362
NZ$3,362
NZ$480 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$4,522
NZ$4,522
NZ$646 per night
includes taxes & fees
Image gallery for CASA DELMARE....Naples pool-villa retreat
9.89.8 out of 10 rating
Exceptional
(16 reviews)
CASA DELMARE....Naples pool-villa retreat
Naples, FL
8% off
Price is NZ$6,637
NZ$6,637
NZ$948 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$4,383
NZ$4,383
NZ$626 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$5,763
NZ$5,763
NZ$823 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
(18 reviews)
New Listing: Charming Pool Home 1/2 mile to Lowdermilk Beach Park!
Naples, FL
8% off
Price is NZ$9,262
NZ$9,262
NZ$1,323 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$7,696
NZ$7,696
NZ$1,099 per night
includes taxes & fees
Image gallery for Pool Home in the Heart of Naples!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Pool Home in the Heart of Naples!
Naples, FL
7% off
Price is NZ$5,915
NZ$5,915
NZ$845 per night
includes taxes & fees
Image gallery for NEW POOL! Naples Home 2 miles to Beach/5th Ave, 2 King Beds, Hot Tub, Bikes
1010 out of 10 rating
Exceptional
(9 reviews)
NEW POOL! Naples Home 2 miles to Beach/5th Ave, 2 King Beds, Hot Tub, Bikes
Naples, FL
7% off
Price is NZ$3,354
NZ$3,354
NZ$479 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$4,146
NZ$4,146
NZ$592 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$4,947
NZ$4,947
NZ$707 per night
includes taxes & fees
Image gallery for Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
Naples, FL
12% off
Price is NZ$3,638
NZ$3,638
NZ$520 per night
includes taxes & fees
Image gallery for The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
9.89.8 out of 10 rating
Exceptional
(8 reviews)
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Naples, FL
14% off
Price is NZ$3,214
NZ$3,214
NZ$459 per night
includes taxes & fees
Image gallery for Great Low Holiday Rates! 5 min to Gulf Beaches.
1010 out of 10 rating
Exceptional
(46 reviews)
Great Low Holiday Rates! 5 min to Gulf Beaches.
Naples, FL
7% off
Price is NZ$1,601
NZ$1,601
NZ$229 per night
includes taxes & fees
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Find the best place to stay - Fifth Avenue South
Bellasera Resort
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
2,179 reviews(2,179 reviews)
Downtown Naples Beach Condo, Half block from Famous 5th Ave
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
20 reviews(20 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
9 reviews(9 reviews)
A beautiful modern luxury villa
Sleeps 12 · 4 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Coastal Chic: Newly Renovated 2BR Condo in Old Naples, Steps from the Beach!
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
13 reviews(13 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)
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