Vacation rentals with a pool in Naples

4.99 out of 5 average rating, 159 reviews

Pool House+Game Room, Moments to Beach & Downtown

Welcome to our Happy Place! This fully renovated Naples retreat sleeps 6 and blends modern comfort with family fun. Enjoy a bright open-plan living area, chef’s kitchen, and 3 bedrooms including a master with pool access. Step outside to your private screened oasis with heated pool, lounge seating, grill, canal and golf course views. The garage game room offers ping-pong foosball & arcade basketball. Just minutes to beaches, dining, and downtown, it’s the perfect getaway for relaxation and play.

LocationFamilyComfort

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, 133 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.

FamilyLocationNearby

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, 158 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!

ValueFamilyBackyard

4.96 out of 5 average rating, 156 reviews

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.

Home in East Naples

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).

ValueLocationLayout

4.95 out of 5 average rating, 169 reviews

An outdoor space is shown, featuring two lounge chairs with decorative pillows, positioned beneath a blue umbrella. A sleek, modern side table sits between them, complemented by a vibrant arrangement of flowers. Water fountains gently spray into the clear pool, surrounded by lush greenery.

Home in Naples Park

577 SunnyDaze | Private Heated Pool | Walk 2 Beach

Welcome to 577 Sunny Daze! Located just 4 blocks from the gorgeous, white sands of Vanderbilt Beach, this heated pool home blends easy beach living w/ inviting coastal comfort throughout. Step outside to your private, lush tropical backyard, where the heated pool, tropical palms, & lush greenery create a peaceful oasis - perfect for morning coffee, afternoon swims, or evenings under the stars! If you've come to soak up the warm Florida sunshine, Sunny Daze is the perfect place to vacation!

LocationFamilyQuiet

4.93 out of 5 average rating, 100 reviews

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.

Condo in Old Naples

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!

ValueFamilyNearby

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

Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

LocationValueParks

An expansive lanai features a shimmering pool with a waterfall-edge spa and in-pool loungers. The outdoor space is surrounded by a screened enclosure, providing views of well-kept greenery. A comfortable seating area and dining space are visible in the background, enhancing the outdoor living experience.

5.0 out of 5 average rating, 32 reviews

Pool Home Minutes to the Beach

Enjoy our family’s bright, renovated home and experience indoor/outdoor Florida living at its best! The open floor plan living area has high vaulted ceilings and fully-retractable glass sliders that open out to a beautiful, south-facing lanai featuring a brand-new, heated, salt-water pool complete with a waterfall-edge spa, a sun shelf and in-pool loungers! Perfect for entertaining and outfitted with all new outdoor furniture including a new sofa & lounge chairs, dining table & grill.

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Apartment in North Naples

A large community pool is framed by a spacious patio area, with lounge chairs neatly arranged around it. A clubhouse with a distinctive roof is visible in the background, surrounded by palm trees and lush landscaping. The sky is partly cloudy, contributing to a bright atmosphere.

4.86 out of 5 average rating, 120 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.)

ValueFamilyPool

A spacious driveway leads to a charming single-family home surrounded by lush greenery. Tall palm trees and vibrant landscaping frame the entrance, enhancing the serene ambiance of the retreat. The home is set back from the road, offering a private and tranquil atmosphere.

4.93 out of 5 average rating, 166 reviews

La Dolce Vita

Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

LocationFamilyLaundry

4.99 out of 5 average rating, 148 reviews

A spacious living area is presented with two gray sofas and two blue armchairs arranged around a decorative coffee table. A large television is mounted on the wall, and natural light filters through the plantation shutters, illuminating the room's light-colored tile flooring.

Home in Bonita Springs

Bonita Retreat: Heated Pool - Minutes to Beach

We know that you’ll love it here – whether you spend your time lounging by our pool, or at beautiful Barefoot Beach, less than 3 miles away. Our home is close to everything, so many beautiful beaches, great shopping and world class restaurants. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. This is our own vacation home, so we’ve made every effort to make it as comfortable and convenient as possible.

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