Vacation rentals with a pool in Old Naples

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.

4.96 out of 5 average rating, 135 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.

4.9 out of 5 average rating, 186 reviews

Downtown Condo at Naples Pier Beach

Come enjoy a restful beach escape at the Naples Mariner, formerly a beautiful Motel built in 1966! Relax while enjoying your fully renovated condo located 60 yards from the Olde Naples Fishing Pier beach and 1 block from the 3rd Street Shops/Restaurants. A quick drive, bike or walk 1 mile north will place you on 5th Avenue - an area of shops, restaurants, bars and a playhouse. The condo has one designated parking spot, wifi, washer/dryer on premises, heated pool, courtyard & more. 'Sea' Ya!

CleanlinessPoolComfort

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.

4.94 out of 5 average rating, 159 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!

The image showcases a bright, inviting pool area featuring clear blue water illuminated by string lights above, creating a relaxed atmosphere. Surrounding spaces include a cozy living room with comfortable seating and a spacious kitchen area with modern fixtures and finishes.

4.96 out of 5 average rating, 156 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).

A bright and airy living area features a comfortable sofa paired with decorative pillows. A glass coffee table rests atop tiled flooring, while a dining table is positioned nearby. A flat-screen TV is mounted on the wall, and wall art adds a coastal touch.

4.93 out of 5 average rating, 102 reviews

Luxury 2-Bedroom. Steps to Naples Beach & Town.

**Newly renovated, reopened December 2024** Spend your Naples getaway in this completely renovated sun drenched, luxury corner unit. Cross the street to the sunny beaches of the Gulf of Mexico. Stroll to the famous Naples Fishing Pier. Walk a block to 3rd St S for fine dining, casual eateries, boutiques, and more. Relax indoors with 3 flat-screen TV's or by the pool. At the end of your day grab your beach chair an view the spectacular Naples sunsets. It does not get any better than this!

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.

4.92 out of 5 average rating, 141 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.

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.

4.98 out of 5 average rating, 129 reviews

Fun At The Beach

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier (rebuilding currently) and 3rd Ave 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 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 refrigerator.

Hospitality

4.96 out of 5 average rating, 101 reviews

Luxury Private Retreat with New Pool in Naples

Welcome to The Park Villa, a serene private retreat in the heart of Naples. Nestled among nature, this peaceful haven features a brand-new salt water heated pool and is just minutes from the Gulf of Mexico's beautiful beaches and vibrant downtown Naples, with its top restaurants and shops. Situated next to a regional park with the largest freshwater lake in Collier County, enjoy stunning views of the park and spot local wildlife like iguanas and tropical birds from your backyard.

A private heated pool is surrounded by lounge chairs and umbrellas, set against a vibrant sunset sky. Lush landscaping frames the area, enhancing the secluded feel. A shaded outdoor bar area is visible in the background, inviting relaxation and social gatherings.

4.88 out of 5 average rating, 126 reviews

Outdoor Kitchen | Heated Pool Near Beach + 5th Ave

Your oasis awaits! Beyond the doors of this impeccably renovated home you'll find a private, heated pool with a fantastic, fenced-in, backyard with mango trees, tropical vegetation & string lights. Beach towels, gear, and loungers are provided so all you need is your suit! Work remotely from the office areas and grill out each evening (propane grill provided). Need space for a crowd? We have multiple homes within walking distance available for large groups.

4.78 out of 5 average rating, 146 reviews

Beautifully private homeHeated Pool/Spa and Cabana

No sargassum or seaweed in Naples! We are close to Naples Community Park and downtown Naples and beaches, perfect location. Unique one of a kind property, This house has been beautifully remodeled with Stunning Carrera marble floors, upgraded 4 bedroom 2 bath home with a separate pool house suite with its own kitchen and full bath that sleeps 4 guests. Beautiful landscaped yards with amazing pool. Only minutes to the beach. Private outdoor shower.

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.

4.99 out of 5 average rating, 141 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.

4.92 out of 5 average rating, 267 reviews

Heated Salt Pool Retreat• Minutes to 5th ave Beach

Discover your sun-soaked Naples retreat — a private, family-friendly sanctuary with a year-round heated saltwater pool, lush outdoor living space, and effortless access to beaches and vibrant 5th Avenue shops. Designed for memorable days around the pool and peaceful nights under the stars, this home blends comfort, convenience, and classic Florida lifestyle.

Popular amenities for Old Naples rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A screened-in pool area features a sparkling pool surrounded by a spacious deck, adorned with potted greenery. Several lounge chairs are positioned nearby, with views of lush landscaping visible through the screens. Sliding glass doors lead into the home, offering a seamless connection to indoor spaces.

4.98 out of 5 average rating, 128 reviews

Naples Retreat: Heated Pool - Minutes to Beach

An inviting lounge area features a spacious layout with contemporary furnishings. Natural light floods the room through large glass doors that open to a private swimming pool. Decorative plants enhance the aesthetic, while a modern kitchen is visible in the background.

4.92 out of 5 average rating, 99 reviews

The Lounge| Modern,Pool, Privacy, 10min Beach/5th

4.95 out of 5 average rating, 173 reviews

Private Pool · 4 mi to Beach · Walk to Dining

The serene backyard features a heated in-ground pool surrounded by lush landscaping and a hot tub. A screened patio offers a dining table and lounge area with inviting cushions. The open concept kitchen and living space are visible, showcasing modern appliances and ample seating for relaxation.

4.95 out of 5 average rating, 107 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

4.97 out of 5 average rating, 115 reviews

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

4.99 out of 5 average rating, 160 reviews

Pool House+Game Room, Moments to Beach & Downtown

An outdoor pool area is presented within a screened enclosure, featuring a clear blue pool. Two chaise lounges with towels sit alongside the pool, and lush greenery frames the space, providing a serene backdrop under a partly cloudy sky.

4.92 out of 5 average rating, 115 reviews

Elegant house w/heated Private Pool

An inviting outdoor space features a heated pool and spa, enclosed by a fine mesh screen. Comfortable seating areas are arranged nearby, complemented by lush greenery. Sunlight streams through the enclosure, highlighting the tranquil atmosphere of this private oasis.

4.91 out of 5 average rating, 138 reviews

Private Oasis in the of Naples Heated Pool/Spa

Condo rentals with a pool

4.94 out of 5 average rating, 120 reviews

A cozy living area features a spacious light-colored sofa and two armchairs, complemented by a glass-topped coffee table. A ceiling fan provides airflow, while natural light pours in through large glass doors. A television is mounted on the wall, enhancing the room's functionality.

Condo in Park Shore

Lush tropical 1st floor getaway in Naples

4.92 out of 5 average rating, 173 reviews

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

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

AccuracyAmenitiesHospitality

4.96 out of 5 average rating, 106 reviews

A serene courtyard features a large pool surrounded by lounge chairs and palm trees. An oversized spa is positioned adjacent to the pool, with lush green foliage framing the scene, offering a sense of tranquility and relaxation in the outdoor space.

Condo in Naples Park

The Sunset @ Naples Boutique | Walk 2 Beaches

4.93 out of 5 average rating, 138 reviews

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

Beautiful Pool 5m to the Beach Downtown & Shopping

4.96 out of 5 average rating, 340 reviews

A spacious pool area is surrounded by lush palm trees and vibrant flowers. The water is calm, with small fountains creating gentle ripples. Loungers line the pool's edge, inviting relaxation under the sun. Sunlight reflects off the surface, enhancing the serene atmosphere.

Condo in Lely Resort

Lely Greenlinks Golf Resort Luxury Condo

Condo in Fort Myers Beach

Lovers Key Resort/Ft Myers Beach/Condo/Pool/View

4.94 out of 5 average rating, 191 reviews

4.9 out of 5 average rating, 119 reviews

A spacious lanai features two vibrant green chairs and a small table, overlooking a tranquil body of water. Lush greenery and a wooden bridge are visible, creating a serene view that enhances the outdoor living experience.

Condo in Park Shore

Park Shore Resort258 Top Loc. View, Pool, Tennis +

Condo in Fort Myers Beach

A panoramic view showcases a sparkling heated swimming pool surrounded by lounge chairs, with the beach and Gulf of Mexico visible in the background. Soft waves lap at the shore while sunbathers can be seen enjoying the sandy area. Lush palm trees frame the scene.

Beachfront fully equipped apartment

4.91 out of 5 average rating, 128 reviews

Other vacation rentals with a pool

A serene pool area is surrounded by lush greenery and palm trees, featuring a tiled patio that leads to the pool. Comfortable lounge chairs with colorful towels are positioned for relaxation. The outdoor space is complemented by a Tiki hut, adding charm and shade.

4.96 out of 5 average rating, 52 reviews

Chic Pool Naples Beach House

Superhost

Apartment in Old Naples

Waterfront Condo near Tin City |Balcony + views|

4.71 out of 5 average rating, 14 reviews

Superhost

Apartment in Old Naples

Modern & Chic 5th Ave Historic Naples

5.0 out of 5 average rating, 4 reviews

4.9 out of 5 average rating, 21 reviews

Apartment in Old Naples

Modern 5th Ave Beach Condo!

An aerial view captures the condo complex positioned near the Gulf of Mexico. The scene features the peaceful sea, sandy beach, and palm trees, with a glimpse of the community pool nestled within the property.

5.0 out of 5 average rating, 19 reviews

Old Naples Beach Condo

An aerial view captures the coastal surroundings, highlighting vibrant ocean hues and the sandy beach in proximity. The landscape showcases a mix of residential homes and palm trees, alongside a glimpse of the community pool and nearby streets leading to the beach.

5.0 out of 5 average rating, 17 reviews

Luxury Charmer steps to Naples Pier & beach

An aerial view showcases a private backyard with a sparkling swimming pool and a hot tub. A white umbrella provides shade over a lounged area, with comfortable seating options visible nearby. Lush green grass surrounds the pool area, enhancing the outdoor space.

4.86 out of 5 average rating, 58 reviews

Your Perfect Escape in the Heart of South Naples

A single-story home is set amidst a lush green lawn, featuring a tiled roof and arched windows. Palm trees and shrubs frame the entrance, which is highlighted by a welcoming front porch. The driveway leads to a spacious garage, enhancing the overall curb appeal.