Holiday rentals near Fifth Avenue South
We found 4,309 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:19 Sept - 26 Sept
Image gallery for 6-bedroom vacation home just 3 minutes to Naples Beach with 3 king ensuites.
1010 out of 10 rating
Exceptional
(40 reviews)
6-bedroom vacation home just 3 minutes to Naples Beach with 3 king ensuites.
Naples, FL
11% off
Price is AU$7,445
AU$7,445
AU$1,064 per night
includes taxes & fees
Image gallery for Just 2 block walk to the Gulf of Mexico Beaches in Olde Naples
1010 out of 10 rating
Exceptional
(8 reviews)
Just 2 block walk to the Gulf of Mexico Beaches in Olde Naples
Naples, FL
8% off
Price is AU$10,234
AU$10,234
AU$1,462 per night
includes taxes & fees
Image gallery for Beach, Heated Pool, Pets, 2 Masters w Kings, Bunk Beds
1010 out of 10 rating
Exceptional
(19 reviews)
Beach, Heated Pool, Pets, 2 Masters w Kings, Bunk Beds
Naples, FL
7% off
Price is AU$3,911
AU$3,911
AU$559 per night
includes taxes & fees
Image gallery for Relaxing PRIVATE Vacation Home at Vanderbilt Beach - FREE WIGGINS PARK PASS
1010 out of 10 rating
Exceptional
(21 reviews)
Relaxing PRIVATE Vacation Home at Vanderbilt Beach - FREE WIGGINS PARK PASS
Naples, FL
8% off
Price is AU$3,271
AU$3,271
AU$467 per night
includes taxes & fees
Image gallery for Modern Coastal Cottage 1.5 miles to Beach
1010 out of 10 rating
Exceptional
(51 reviews)
Modern Coastal Cottage 1.5 miles to Beach
Naples, FL
8% off
Price is AU$4,730
AU$4,730
AU$676 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 AU$3,349
AU$3,349
AU$478 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 AU$3,383
AU$3,383
AU$483 per night
includes taxes & fees
Image gallery for Beautiful lake view with large lanai & heated private pool, 10 mins to beach!
1010 out of 10 rating
Exceptional
(59 reviews)
Beautiful lake view with large lanai & heated private pool, 10 mins to beach!
Naples, FL
9% off
Price is AU$4,179
AU$4,179
AU$597 per night
includes taxes & fees
Image gallery for 833 Naples Heated Pool Home - 3BR3BA plus Den - Only minutes to the Beach
1010 out of 10 rating
Exceptional
(25 reviews)
833 Naples Heated Pool Home - 3BR3BA plus Den - Only minutes to the Beach
Naples, FL
7% off
Price is AU$4,019
AU$4,019
AU$574 per night
includes taxes & fees
Image gallery for Lely Masters Reserve: Golf, Players club, Private pool, Ultimate comfort!
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Lely Masters Reserve: Golf, Players club, Private pool, Ultimate comfort!
Naples, FL
11% off
Price is AU$6,199
AU$6,199
AU$886 per night
includes taxes & fees
Image gallery for Wonderful Beach Getaway With a Saltwater Pool
1010 out of 10 rating
Exceptional
(206 reviews)
Wonderful Beach Getaway With a Saltwater Pool
Naples, FL
7% off
Price is AU$2,744
AU$2,744
AU$392 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 AU$5,372
AU$5,372
AU$767 per night
includes taxes & fees
Image gallery for Tranquil 3br/2ba Home with Heated Saltwater Pool
1010 out of 10 rating
Exceptional
(41 reviews)
Tranquil 3br/2ba Home with Heated Saltwater Pool
Naples, FL
7% off
Price is AU$3,430
AU$3,430
AU$490 per night
includes taxes & fees
Image gallery for Charming 3 Bedroom home w/plenty in & outdoor space, perfect for every occasion.
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Charming 3 Bedroom home w/plenty in & outdoor space, perfect for every occasion.
Naples, FL
5% off
Price is AU$1,519
AU$1,519
AU$217 per night
includes taxes & fees
Image gallery for Mini-mansion ... Downtown Where the Action is & walk to Beach
8.28.2 out of 10 rating
Very good
(11 reviews)
Mini-mansion ... Downtown Where the Action is & walk to Beach
Naples, FL
8% off
Price is AU$6,625
AU$6,625
AU$946 per night
includes taxes & fees
Image gallery for Naples Park Pool & Spa Home 1 Mile to Beach and Tropical Oasis Fenced Yard.
1010 out of 10 rating
Exceptional
(20 reviews)
Naples Park Pool & Spa Home 1 Mile to Beach and Tropical Oasis Fenced Yard.
Naples, FL
8% off
Price is AU$4,316
AU$4,316
AU$617 per night
includes taxes & fees
Image gallery for Mid Century Modern Vacation Home
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Mid Century Modern Vacation Home
Naples, FL
8% off
Price is AU$10,615
AU$10,615
AU$1,516 per night
includes taxes & fees
Image gallery for Naples Best Value Luxury 4 Bedroom Heated Pool Spa Bikes Spacious Backyard
1010 out of 10 rating
Exceptional
(80 reviews)
Naples Best Value Luxury 4 Bedroom Heated Pool Spa Bikes Spacious Backyard
Naples, FL
11% off
Price is AU$2,972
AU$2,972
AU$425 per night
includes taxes & fees
Image gallery for Beautiful Home! Two Masters! Less than One Mile to the Beach!
1010 out of 10 rating
Exceptional
(75 reviews)
Beautiful Home! Two Masters! Less than One Mile to the Beach!
Naples, FL
7% off
Price is AU$4,661
AU$4,661
AU$666 per night
includes taxes & fees
Image gallery for Park Shore Resort: gorgeous view, Best Location, Tennis, Pickleball, Beach
9.89.8 out of 10 rating
Exceptional
(155 reviews)
Park Shore Resort: gorgeous view, Best Location, Tennis, Pickleball, Beach
Naples, FL
6% off
Price is AU$1,874
AU$1,874
AU$268 per night
includes taxes & fees
Image gallery for Enchanting Villa with Private Pool, Bicycles, and Full Amenities; 7-day discount
1010 out of 10 rating
Exceptional
(67 reviews)
Enchanting Villa with Private Pool, Bicycles, and Full Amenities; 7-day discount
Naples, FL
7% off
Price is AU$2,779
AU$2,779
AU$397 per night
includes taxes & fees
Image gallery for Vanderbilt Beach, New Home, heated saltwater pool and spa.
1010 out of 10 rating
Exceptional
(62 reviews)
Vanderbilt Beach, New Home, heated saltwater pool and spa.
Naples, FL
7% off
Price is AU$4,007
AU$4,007
AU$572 per night
includes taxes & fees
Image gallery for ONE BLOCK to the beach, Restaurants & Shopping!!!
1010 out of 10 rating
Exceptional
(31 reviews)
ONE BLOCK to the beach, Restaurants & Shopping!!!
Naples, FL
8% off
Price is AU$3,185
AU$3,185
AU$455 per night
includes taxes & fees
Image gallery for Renovated Condo in Prime Location: Beaches, Restaurants, Shops, the Arts & More!
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Renovated Condo in Prime Location: Beaches, Restaurants, Shops, the Arts & More!
Naples, FL
7% off
Price is AU$3,030
AU$3,030
AU$433 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
Bellasera Resort
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
2,176 reviews(2,176 reviews)
Downtown Naples Beach Condo, Half block from Famous 5th Ave
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
19 reviews(19 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)
Classic Beach-Style Cottage
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
41 reviews(41 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)
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