Holiday rentals near Waterside Shops
We found 9,446 holiday rentals — enter your dates for availability
Select the perfect private holiday rental that's near Waterside Shops. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as parking and a pool. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Waterside Shops
Showing deals for:1 Aug - 8 Aug
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 NZ$8,898
NZ$8,898
NZ$1,271 per night
includes taxes & fees
Image gallery for NEW REMODEL Steps from private beach access! 4 BR Family Friendly CLEAN
9.49.4 out of 10 rating
Exceptional
(30 reviews)
NEW REMODEL Steps from private beach access! 4 BR Family Friendly CLEAN
Fort Myers Beach, FL
8% off
Price is NZ$4,823
NZ$4,823
NZ$689 per night
includes taxes & fees
Image gallery for 6 Bedroom,5 Bath pool home with 120"tv in living room & 160" pool tv
1010 out of 10 rating
Exceptional
(144 reviews)
6 Bedroom,5 Bath pool home with 120"tv in living room & 160" pool tv
Fort Myers Beach, FL
7% off
Price is NZ$10,125
NZ$10,125
NZ$1,446 per night
includes taxes & fees
Image gallery for The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Naples, FL
11% off
Price is NZ$3,931
NZ$3,931
NZ$562 per night
includes taxes & fees
Image gallery for 2 Blocks To Beach, Large Private Pool, 4 bedroom home with 2 separate suites
9.49.4 out of 10 rating
Exceptional
(28 reviews)
2 Blocks To Beach, Large Private Pool, 4 bedroom home with 2 separate suites
Fort Myers Beach, FL
8% off
Price is NZ$5,393
NZ$5,393
NZ$770 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 NZ$5,119
NZ$5,119
NZ$731 per night
includes taxes & fees
Image gallery for The Gilded Palm - Naples, 4 Blocks to Beach, 1/2 Block to 5th Ave Downtown, Pool
1010 out of 10 rating
Exceptional
(26 reviews)
The Gilded Palm - Naples, 4 Blocks to Beach, 1/2 Block to 5th Ave Downtown, Pool
Naples, FL
8% off
Price is NZ$2,863
NZ$2,863
NZ$409 per night
includes taxes & fees
Image gallery for Brand New Luxury Pool & Spa Home Near Beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Brand New Luxury Pool & Spa Home Near Beach!
Naples, FL
7% off
Price is NZ$4,594
NZ$4,594
NZ$656 per night
includes taxes & fees
Image gallery for Marco Island! “On the Island” Pool/Spa/Waterfall Oasis Gorgeous Tropical Home
1010 out of 10 rating
Exceptional
(23 reviews)
Marco Island! “On the Island” Pool/Spa/Waterfall Oasis Gorgeous Tropical Home
Marco Island, FL
7% off
Price is NZ$4,098
NZ$4,098
NZ$585 per night
includes taxes & fees
Image gallery for Florida Canal Balcony view- Quiet Neighborhood and 10 minutes to the Beach!
9.29.2 out of 10 rating
Wonderful
(21 reviews)
Florida Canal Balcony view- Quiet Neighborhood and 10 minutes to the Beach!
Bonita Springs, FL
7% off
Price is NZ$2,138
NZ$2,138
NZ$305 per night
includes taxes & fees
Image gallery for Sunny Pool & Spa inside Lanai! You will Love this fully furnished 3bdrm Home!
1010 out of 10 rating
Exceptional
(94 reviews)
Sunny Pool & Spa inside Lanai! You will Love this fully furnished 3bdrm Home!
Marco Island, FL
8% off
Price is NZ$9,747
NZ$9,747
NZ$1,392 per night
includes taxes & fees
Image gallery for Lakeview Seashell Cottage— Pets Welcome! Sleeps 4
1010 out of 10 rating
Exceptional
(51 reviews)
Lakeview Seashell Cottage— Pets Welcome! Sleeps 4
Bonita Springs, FL
7% off
Price is NZ$1,662
NZ$1,662
NZ$237 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 NZ$2,381
NZ$2,381
NZ$340 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
(66 reviews)
Enchanting Villa with Private Pool, Bicycles, and Full Amenities; 7-day discount
Naples, FL
7% off
Price is NZ$3,148
NZ$3,148
NZ$450 per night
includes taxes & fees
Image gallery for Old Florida Canal Home
1010 out of 10 rating
Exceptional
(38 reviews)
Old Florida Canal Home
Bonita Springs, FL
7% off
Price is NZ$5,555
NZ$5,555
NZ$794 per night
includes taxes & fees
Image gallery for 16th Fl Marco Island 2 BR 2 bath.Spectacular Beachfront Views!
9.89.8 out of 10 rating
Exceptional
(36 reviews)
16th Fl Marco Island 2 BR 2 bath.Spectacular Beachfront Views!
Marco Island, FL
7% off
Price is NZ$3,075
NZ$3,075
NZ$439 per night
includes taxes & fees
Image gallery for New Stilt Home: Heated Pool, Near Beach & Times Sq
1010 out of 10 rating
Exceptional
(13 reviews)
New Stilt Home: Heated Pool, Near Beach & Times Sq
Fort Myers Beach, FL
6% off
Price is NZ$4,934
NZ$4,934
NZ$705 per night
includes taxes & fees
Image gallery for Come enjoy paradise on Isles of Capri in Naples, FL for your next vacation!
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Come enjoy paradise on Isles of Capri in Naples, FL for your next vacation!
Naples, FL
9% off
Price is NZ$2,947
NZ$2,947
NZ$421 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
(79 reviews)
Naples Best Value Luxury 4 Bedroom Heated Pool Spa Bikes Spacious Backyard
Naples, FL
12% off
Price is NZ$4,009
NZ$4,009
NZ$573 per night
includes taxes & fees
Image gallery for Naples Vanderbilt Beach Getaway
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Naples Vanderbilt Beach Getaway
Naples, FL
8% off
Price is NZ$4,278
NZ$4,278
NZ$611 per night
includes taxes & fees
Image gallery for Wonderful Beach Getaway With a Saltwater Pool
1010 out of 10 rating
Exceptional
(203 reviews)
Wonderful Beach Getaway With a Saltwater Pool
Naples, FL
7% off
Price is NZ$3,394
NZ$3,394
NZ$485 per night
includes taxes & fees
Image gallery for Royal Palm House 2 story home near Naples Bay and Beach
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Royal Palm House 2 story home near Naples Bay and Beach
Naples, FL
7% off
Price is NZ$2,103
NZ$2,103
NZ$300 per night
includes taxes & fees
Image gallery for Vanderbilt Beach, New Home, heated saltwater pool and spa.
1010 out of 10 rating
Exceptional
(60 reviews)
Vanderbilt Beach, New Home, heated saltwater pool and spa.
Naples, FL
8% off
Price is NZ$4,339
NZ$4,339
NZ$620 per night
includes taxes & fees
Image gallery for Fun in the Sun! Prime Location - Beaches, Restaurants, Shops, the Arts & More!
1010 out of 10 rating
Exceptional
(19 reviews)
Fun in the Sun! Prime Location - Beaches, Restaurants, Shops, the Arts & More!
Naples, FL
7% off
Price is NZ$2,901
NZ$2,901
NZ$414 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Waterside Shops
Edison Beach House
Sleeps 4 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
1,319 reviews(1,319 reviews)
Lazy Cuckoo Inn
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
200 reviews(200 reviews)
GullWing Beach Resort
Sleeps 6 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
917 reviews(917 reviews)
Newly Renovated🌴Coral Reef Villa - Steps away from beach/ private heated pool🌞
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
48 reviews(48 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