Vacation rentals with a pool in Old Naples

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Top-rated rentals with a pool in Old Naples

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
A modern pool area is featured with a spacious swimming pool surrounded by a screened-in lanai. Lounge seating and vibrant cabanas are positioned nearby, providing shaded relaxation. An adjacent game room is visible, equipped with a pool table and foosball table under unique lighting.
Home in Naples
4.95 out of 5 average rating, 117 reviews

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

Top guest favourite
A spacious living area features modern white armchairs positioned beside a stylish sofa. A table is set with decorative placements, and light enters through large sliding glass doors, framing views of lush greenery outside.
Condo in Park Shore
4.91 out of 5 average rating, 164 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

Guest favourite
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, 102 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.

Top guest favourite
The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.
Condo in Old Naples
4.98 out of 5 average rating, 116 reviews

FUN AT THE BEACH

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier( to be rebuilt)and 3rd Ave Famous Dining and Shopping. Private entrance to unit with designated parking. The pool is outside your door for easy access. The unit provides a master suite with a king mattress and the extra room has 2 twins that can convert into a king. Please request upon booking. A laundry facility is located on the premises. Kitchenette provides cooktop and microwave/convection oven & a small refridgerator.

Top guest favourite
A sunset view features a wooden pier stretching over waves, with silhouettes of people gathering at the end. Warm hues of orange and yellow illuminate the sky, creating a serene backdrop against the gently rolling ocean.
Apartment in Naples
4.99 out of 5 average rating, 134 reviews

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

Top guest favourite
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
4.95 out of 5 average rating, 133 reviews

LUXE Oasis | 10 min Beach • HTD Pool+5th Ave •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 favourite
A spacious heated pool invites relaxation, surrounded by lounge chairs placed along the deck. Lush palm fronds frame the view, enhancing the tropical ambiance. The pool area is well-maintained, with clear water reflecting the sun. Parking is visible beyond the poolside greenery.
Condo in Old Naples
4.93 out of 5 average rating, 129 reviews

NEW! ONE BLOCK to the Beach, Restaurants & Shops!

Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

Top guest favourite
An open living area features a cozy seating arrangement with a brown armchair and a textured ottoman. Wall art depicting botanical themes complements the neutral walls. A modern kitchen bar with three stools is visible, lending to the inviting and functional design of the space.
Home in Naples Park
4.99 out of 5 average rating, 148 reviews

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Top guest favourite
A modern living area is highlighted by a white sectional sofa and a circular glass dining table surrounded by stylish white chairs. Large windows provide views of a tranquil outdoor space with greenery and water, complementing the bright interior decor.
Condo in Naples
4.92 out of 5 average rating, 131 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

**Condo - Naples Modern Retreat** Welcome to Naples Modern Retreat, a fully renovated 2 bedroom, 2 bathroom condo nestled in a Tennis Resort in the heart of Naples, Florida. 6 miles to downtown and the beaches. This property offers a harmonious blend of scenic views including beach, canal, garden, lake, marina, ocean, pool, and resort vistas, ensuring a stay full of breathtaking beauty and modern luxury. ** Popular Amenities ** 2 bicycles, 5 beach chairs and umbrella

Top guest favourite
Home in Naples Park
4.98 out of 5 average rating, 133 reviews

Walk to Vanderbilt Beach, Pets, 2 Mstrs w Kings

Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...

Guest favourite
A sun setting over the horizon casts a warm glow on the water, creating a serene scene. The beach is lined with soft white sand, and a pier extends into the sea in the distance, framed by a clear sky above.
Home in Naples
4.96 out of 5 average rating, 142 reviews

Beach & Pool Escape – Walk to Naples Hotspots

Modern 3BR/2.5BA Naples home with private pool, perfect for adults seeking comfort and fun. Sleeps 6 with king suite, queen room, and queen-over-queen bunks. Relax poolside or head to the beach with provided chairs, umbrellas, blankets, and coolers. Walk to Botanical Garden, breweries, and dining. High-speed WiFi, Smart TVs, and desks keep you connected if needed. Kid-ready with Pack ’n Play, high chair, and toys.

Top guest favourite
An outdoor living space features a screened lanai overlooking a pool. Comfortable loungers are positioned around the pool. A dining table with multiple chairs is set under a ceiling fan, complemented by a large area rug. The scene is bathed in natural light.
Home in Naples
4.98 out of 5 average rating, 124 reviews

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.

Popular amenities for Old Naples rentals with a pool

When is the best time to visit Old Naples?

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Avg. price$441 CAD$503 CAD$488 CAD$423 CAD$395 CAD$321 CAD$317 CAD$299 CAD$352 CAD$348 CAD$388 CAD$411 CAD
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Quick stats about vacation rentals with a pool in Old Naples

  • Total vacation rentals

    Explore 240 vacation rentals in Old Naples

  • Nightly prices starting at

    Old Naples vacation rentals start at $85 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    170 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    230 of Old Naples vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Old Naples rentals

  • 4.9 Average rating

    Old Naples stays are highly rated by guests—averaging 4.9 out of 5!

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