Vacation rentals with a pool in Old Naples

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.

4.96 out of 5 average rating, 116 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.

4.91 out of 5 average rating, 162 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

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!

A bright living area is furnished with modern white sofas and a dark armchair. Large glass doors lead to the pool area, allowing natural light to fill the room. Vibrant textiles and a ceiling fan enhance the relaxed ambiance of the space.

4.98 out of 5 average rating, 103 reviews

Backyard Oasis - Large heated pool/Wi-fi/Lanai/PS3

Enjoy a great vacation in our beautiful Naples home. With three spacious bedrooms, modern decor, plentiful natural light, and a full kitchen, this upscale home is perfect for groups of friends or families seeking a sunny getaway. Enjoy direct access to a private pool and an ideal location in a safe neighborhood just a short drive from stunning beaches. 8 Min Drive to 3rd Avenue 10 Min Drive to Naples Botanical Garden 12 Min Drive to Naples Pier and Beach Experience Naples With Us & Learn More

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, 100 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.

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, 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.

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.

4.95 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!

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.

4.93 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.

A spacious outdoor area features a rectangular pool surrounded by lounge chairs. A covered seating area is visible to the left, with a shaded structure supported by wooden beams. Lush greenery and palm trees add a tropical ambiance, complementing the exterior of the home.

4.92 out of 5 average rating, 108 reviews

Private Heated Pool | Playset | Near the Beach!

Just minutes from the beach, Flamingo Feliz is a cheerful 3-bedroom getaway with a brand-new pool, cozy tiki lounge, and family-friendly extras. Enjoy smart TVs in every room, a fully stocked kitchen, beach gear, bikes, and plenty of space to relax. The heated pool (heating avail. Oct–May) and outdoor living areas make it perfect for a sunny Florida escape. Located near 5th Ave dining, shops, and Naples' best beaches—everything you need for a laid-back vacation!

4.93 out of 5 average rating, 155 reviews

A refreshing pool area features a heated pool surrounded by lounge chairs and a dining table. An inflatable pink flamingo floats in the water, while colorful umbrellas provide shade. Lush greenery frames the outdoor space, creating a bright and inviting atmosphere.

Home in Naples Park

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

4.91 out of 5 average rating, 126 reviews

The exterior of Turtle Bungalow is framed by tall palm trees and lush greenery. A shaded seating area is arranged under a large umbrella, accompanied by a table and chairs. Decorative elements, such as a small statue and potted plants, enhance the entrance.

Guesthouse in Naples

Turtle Bungalow

Wake up to a chorus of singing birds under the splendid South Florida weather. Brew a coffee in the privacy of your bungalow, and get ready to seize the day. After a fun day at the beach or a productive working session, Turtle Bungalow will be perfect for the relaxation you need. Sit outside and enjoy the peaceful backyard view, pool, and the sweet afternoon breeze. The sun is warm, flowers are blooming… I wouldn’t wait.

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.

4.96 out of 5 average rating, 139 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.

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.

4.98 out of 5 average rating, 123 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 131 reviews

Home in Naples Park

Walk to Vanderbilt Beach, Pets, 2 Mstrs w Kings

4.98 out of 5 average rating, 173 reviews

A spacious houseboat is docked in calm waters, featuring a bright blue canopy atop the upper deck. White exterior walls contrast with the blue and gold accents. Surrounding greenery and nearby boats can be seen, enhancing the serene waterfront setting.

Home in Old Naples

Unique Waterfront Naples Experience

4.88 out of 5 average rating, 26 reviews

Luxury 6BR Retreat w/private Pool beach 3 min away

A modern living area is presented with white furnishings and light wood flooring. An elegant chandelier hangs above, while a linear fireplace adds sophistication. Large windows allow natural light, and artwork adorns the walls, contributing to a stylish and open atmosphere.

5 out of 5 average rating, 19 reviews

Modern Home in Naples w/ Heated Pool

A spacious outdoor area features a large heated pool surrounded by a screened enclosure. Two lounge chairs sit along the poolside, while a dining table with chairs is positioned nearby. Lush greenery and a clear blue sky create a serene setting.

5 out of 5 average rating, 12 reviews

The Marquee of Naples

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.

4.94 out of 5 average rating, 17 reviews

Chic Pool Naples Beach House

Superhost

A modern coastal home features a light-colored facade with distinct gabled roofs. A well-maintained lawn adorned with various plants and flowers surrounds the property, while a white picket fence outlines the front yard. The driveway and walkway lead to the entrance of the inviting residence.

5 out of 5 average rating, 4 reviews

Seaside Park S - Heart of Bayshore District, Pool,

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.

4.95 out of 5 average rating, 130 reviews

Coastal Getaway *Heated Pool *3 King Rooms

Condo rentals with a pool

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 out of 5 average rating, 11 reviews

Old Naples Beach Condo

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.

4.96 out of 5 average rating, 321 reviews

Lely Greenlinks Golf Resort Luxury Condo

Condo in Fort Myers Beach

4.82 out of 5 average rating, 113 reviews

Gulf Views & Sunsets | Estero Beach Tennis 206C

A comfortable living area features a sectional sofa with plush cushions arranged around a glass coffee table. A round dining table with four chairs sits nearby, accompanied by a floor mirror that reflects the light. Warm tones and modern decor create an inviting space.

4.95 out of 5 average rating, 109 reviews

Cool Condo for your Cozy Stay in Lely Resort

An aerial view captures the vibrant coastal community, with turquoise waters meeting sandy beaches in the distance. Palm trees and residential properties create a lush landscape. A private parking lot is visible near the foreground, indicating easy access to the beach and surrounding amenities.

4.98 out of 5 average rating, 55 reviews

Luxury condo. 300 steps to beach & Naples Pier.

4.9 out of 5 average rating, 113 reviews

Condo in Bonita Springs

Bonita Beach and Tennis 5807

4.94 out of 5 average rating, 102 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

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.

4.92 out of 5 average rating, 130 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

Other vacation rentals with a pool

A bright living area is furnished with a white sideboard and a flat-screen TV. Two light-colored sofas with green accents face each other. A dining table with chairs is visible in the background, alongside wall art featuring botanical themes. Soft lighting creates a welcoming space.

4.89 out of 5 average rating, 44 reviews

Renovated Studio Steps to Naples Beach & Downtown!

Superhost

Apartment in Naples

4.83 out of 5 average rating, 6 reviews

Great Condo in East Naples!

5 out of 5 average rating, 7 reviews

Private Heated Pool• Outdoor TV & Gated in Naples

An open living area features light-colored furnishings and natural décor elements. A dining table is set with woven placemats, while large glass doors provide access to a balcony with a view of the marina. Soft textiles enhance the inviting atmosphere.

4.91 out of 5 average rating, 23 reviews

Downtown Marina Retreat

4.96 out of 5 average rating, 53 reviews

The living area showcases a light-filled space with a comfortable seating arrangement, including a large sectional sofa and accent chairs. A round coffee table is positioned on a soft area rug. Large sliding glass doors lead to a private balcony with views of the Gulf.

Condo in Park Shore

The Club at Naples Cay 501 - Gulf Views

A tranquil pool scene is captured at sunset, featuring vibrant orange and pink hues in the sky. A pink inflatable flamingo floats on the water, surrounded by a well-kept pool deck with lounge chairs and umbrellas nearby, framed by lush greenery and palm trees.

5 out of 5 average rating, 21 reviews

Hidden Gem-Central Naples-3 Miles to Town & Beach

A modern outdoor area features a sleek heated pool and jacuzzi, surrounded by landscaped greenery. Glass railings provide unobstructed views of the river. Natural stone surfaces complement the serene environment, creating a peaceful retreat for relaxation.

4.89 out of 5 average rating, 45 reviews

Casa Di Napoli: 2/2 Chic Retreat/Private Pool