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Places to stay near Waterside Shops

Book unique vacation rentals, homes, and more on Airbnb

Top-rated vacation rentals near Waterside Shops

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Naples
4.85 out of 5 average rating, 101 reviews

Guest suite with full privacy

Cozy guest suite with complete privacy. You will have a bedroom, bathroom, & small kitchenette. There is a microwave, coffee maker & small fridge.There is a locked door between the main house and guest suite. The entrance is at the side of the main house with free parking. You will have a small patio by the side door. . There is an additional portable A/C unit which will allow you to adjust your room temperature.Quiet and friendly neighborhood. Close to the beach, restaurants and shopping mall.

Guest favorite
A serene pool area is surrounded by lush tropical landscaping, with palm trees and plants visible in the background. The water reflects soft blue tones under an evening sky, creating a calming atmosphere. Lounge chairs line the pool's edge, inviting relaxation.
Condo in Naples
4.94 out of 5 average rating, 112 reviews

Lush tropical 1st floor getaway in Naples

Whether you're looking for a family-oriented or quiet, romantic vacation, we've got you covered! Our unit is tucked away at the south end of our complex where the trickle of the waterfall outside your lanai is the perfect backdrop to enjoying your morning coffee or perhaps a vacation cocktail! Our unit is completely remodeled in an updated coastal-chinoiserie style that is a combo of classic and contemporary, but also livable (we have two young children). Perfect backdrop to your time in SW FL!

Top guest favorite
A serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.
Home in Naples
4.96 out of 5 average rating, 127 reviews

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

Guest favorite
A spacious screened-in lanai features a heated pool with a shallow area for children. Luxury chaise lounges are positioned near the pool, offering comfortable seating. The outdoor space is designed for relaxation and enjoyment, with clear views of the surrounding greenery.
Home in Naples
4.94 out of 5 average rating, 152 reviews

Lux Oasis | 10 min Beach and 5th Ave•HTD Pool•Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

Top guest favorite
Home in Naples
4.96 out of 5 average rating, 150 reviews

Coastal Getaway *Heated Pool *3 King Rooms

Tropical Oasis Downtown Naples 3 BD/2 BA full house w/ a HEATED pool, outdoor entertaining, BBQ grill, lanai seating/dining for 8, outdoor games, 2 living rooms w/ large TVs (main room has a 75" screen TV), master suite w/ ensuite bathroom & flatscreen TV, all 3 bedrooms have king beds. Close to downtown restaurants/shopping (9 min), beaches/Naples Pier (14 min). DOG POLICY: Only after owner's approval, a non-shedding small dog is allowed with $100 per dog non-refundable fee (2 dog maximum).

Top guest favorite
A modern stilt home is nestled along a canal, featuring a large deck accessible by wooden stairs. Palm trees frame the exterior, while a private dock provides space for a boat. The tranquil setting is enhanced by the soft glow of the sunset.
Home in Naples
4.99 out of 5 average rating, 181 reviews

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

Top guest favorite
A bright living area is presented with a cozy sofa adorned with colorful cushions. A stylish coffee table sits on a soft area rug. A staircase leads to the loft bedroom, while two woven pendant lights hang from the ceiling, enhancing the space's beachy vibe.
Tiny home in Naples
5 out of 5 average rating, 203 reviews

BEACHYVibes TINY House Pickleball Ct Mile to Beach

Located less than one mile from the beach in the center of the city hustle, the minute you step inside our “Tiny House" the beachy vibe gently reminds you of why you came! The 12' living room makes the 400 sq ft space feel more expansive. Sailor’s knot rope tied around anchored cleats create a banister railing to the 6’2” spacious loft bedroom. Nestled below an eat-in kitchen and full bath. The stand alone new construction has a private entrance and luscious outdoor private patio.

Top guest favorite
Home in Naples
4.98 out of 5 average rating, 323 reviews

Garden House-2 Bedroom/2 Bath-Naples / Park Shore

WHOLE HOUSE RENTAL-Intimate quiet setting. 2 miles from the beach and 4 miles from (a 10 minute drive) Downtown / 5th Avenue Naples. The house is within easy walking distance of the Park Shore Area / US41 / Tamiami Trail restaurants and bars. Outdoor hot tub, fire-pit and lush green gardens for a tranquil stay. There are no hidden cleaning fees on this listing which is a huge plus. There are also no hidden cameras or sensors of any kind at the house—your privacy is respected.

Guest favorite
Apartment in Naples
4.85 out of 5 average rating, 113 reviews

Oasis Naples Condo 2BR/2Bath

Soak up the warm southwest Florida sun and enjoy a clean modern home with gorgeous views. This newly renovated condo is a short 5 minute car ride to Naples Beaches and 15 minutes to downtown. Two bedroom, two full bath home is the perfect quiet place for a couple’s retreat or for working remotely with high speed internet. The main pool IS open dawn to dusk!!! It’s a two minute walk within the community! (The smaller pool by the condo is closed and still waiting for completion.)

Top guest favorite
Bungalow in Naples
4.99 out of 5 average rating, 113 reviews

Sugar Beach Bungalow With a Pool!

Come jump in the pool! Put away your wool hats, hang up your parkas, and break out the swim trunks, sunglasses and flip flops. There’s no better way to celebrate summer (or escape winter) than with a relaxing beach vacation. Bring the whole family, roll with a group of friends, or make it a romantic retreat. Whatever the trip, opt for a luxurious vacation rental with all the home amenities you’re used to at home—and some. This incredible beach home has it all!

Guest favorite
Home in Naples
4.94 out of 5 average rating, 353 reviews

Coastal Farmhouse w/ mini Golf, Private Beach &Spa

We welcome you to our high end, next level, brand new Farmhouse, which is conveniently located in the heart of Naples. Only 1.5 miles away from the beach, minutes away from the nearby plaza, which offers dining experience, shops, supermarkets, gas stations, etc. The well-known downtown district is only four miles away and Mercato, if you are looking for nighttime activities. Brand new High-end furniture and beds. Welcome, Home!

Guest favorite
A modern kitchen includes white cabinetry and a large island with seating for three. Stainless steel appliances complement the clean design. Natural light is welcome through nearby windows, enhancing the open layout that connects the kitchen to the main living area.
Home in Naples
4.94 out of 5 average rating, 180 reviews

Family Coastal Home - 1 Mile from Beach

Newly renovated, family-friendly home, a perfect vacation spot. Enclosed yard and private patio. Everything you need for a perfect vacation awaits in this two bedroom home. Only 1.4 miles away from clam pass beach park and the North Gulf Shore beach. And when it’s time to explore you’re a mile from the Villages, a local favourite!

Popular amenities for vacation rentals near Waterside Shops

  1. Airbnb
  2. United States
  3. Florida
  4. Collier County
  5. Naples
  6. Waterside Shops