Holiday rentals with a pool in North Naples

5 out of 5 average rating, 102 reviews

Your Private NaplesBeach Getaway

🌴 Private Oasis 3 mins from Vanderbilt Beach 🌊 Welcome to our slice of paradise in Naples Park, Florida! Nestled 3 minutes away from the pristine sands of Naples Beach, world-famous Mercato Shops & Dining, and Publix/Walmart. Only 15 minute north of 5th Ave Downtown District. Our renovated home features a privately fenced backyard with a new heated saltwater pool, a custom miniature golf zone, and many outdoor games for every guest ❤️ Simply the most perfect cozy retreat for your beach getaway🏖️

5 out of 5 average rating, 21 reviews

Heated Pool King Bed, Beach 1 Mile, Lg fenced yard

Heated Pool, Vanderbilt Beach and Wiggins State park beach under 5 min., plenty of fine dining, fast food, Mercato, Publix, Walmart Supercenter etc. Recently renovated with stylish coastal decor, offering a completely stocked kitchen, large bathroom with shower, Bedrooms have 50' HD Smart Tvs and the living room has a 65' Smart TV. Large Lanai with Outdoor furniture, TV and Dining table for 4, BBQ , Washer/Dryer and More! Please Note : This is a side by side duplex, the backyard/pool are shared.

4.92 out of 5 average rating, 166 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.

Apartment 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!

An open living area is viewed from a dining space, featuring a large wooden table set for meals. Comfortable seating is arranged around a coffee table, with large windows providing an unobstructed view of the pool area outside. A television is positioned on a black media console.

4.97 out of 5 average rating, 233 reviews

3 bdrm up to 6 guest pool walk to Vanderbilt Beach

Our home is located in the heart of North Naples. It is less than 1mi. to the beautiful white sand Vanderbilt Beach. Our brand new remolded non-smoking, 3 bedroom 2 bath home is surrounded by numerous local restaurants, entertainment and shopping centers. It's less than 1mi to the newest Naples hot spot "The Mercato". It's 10 min to downtown Naples, 15mi to Miromar Outlets SWFL top place to shop. You can relax in our open floor plan that leads out to the deck of private Pool and hot tub.

A private outdoor space features a saltwater pool and hot tub, surrounded by lush greenery. Comfortable seating arrangements include a fire pit and outdoor dining area, all sheltered under a screened enclosure, providing a tranquil setting for relaxation.

4.97 out of 5 average rating, 208 reviews

LUXE: Beach Home w/ Screened Pool & Spa, BBQ

This 2,000-square foot stunner has a saltwater pool, hot tub, two-car garage, three bedrooms and four bathrooms. There are bikes and beach accessories on site to take to the beach. Guest who is booking the reservation must be 26 years or older. There is a fee of $100/night per person for any guest over 7 in total up to a maximum of 9 guests. For example, if you have 8 guests, then the extra charge will be $100 per night. Please enter the exact number of guests before completing your booking.

A spacious outdoor area encompasses a newly heated pool, surrounded by tropical landscaping. Lounge chairs are positioned near the pool, while dining tables and colorful umbrellas provide shade. A BBQ grill is accessible, with additional seating visible under the covered patio area.

4.93 out of 5 average rating, 147 reviews

606 SeaRenity Resort • Designer Home w/Heated Pool

Welcome to 606 SeaRenity! This completely remodeled home features a SOUTHERN EXPOSURE, HEATED POOL & is surrounded by lush tropical landscaping! Located in the heart of the Vanderbilt Beach area meaning world class, white sand beaches are easily accessible by walking, biking or driving. Near the Ritz Carlton, Turtle Club & LaPlaya this home is sure to please. Supermarkets, Shopping, Dining & Nightlife including Mercato Shopping & Dining District, Naples best attractions just minutes away.

4.87 out of 5 average rating, 141 reviews

The screened patio area features a solar-heated pool surrounded by lush greenery. Comfortable lounge chairs are positioned alongside, and a gas BBQ grill is visible nearby. Floating pool toys and colorful cushions add a relaxed touch to the inviting atmosphere.

Bungalow in Naples Park

Little Treasure House minutes from Beach & Mercato

Enjoy a sun-soaked retreat in Naples Park! This inviting vacation home boasts a solar-heated pool, perfect for families, couples, or friends seeking a getaway or staycation. With easy access to Vanderbilt Beach (10 mins by bike) and the vibrant Mercato for shopping, dining, and entertainment, it's an ideal location. This cozy home away from home offers all essentials for a relaxing stay, just pack your sunglasses and bathing suit and immerse yourself in the quintessential Florida lifestyle!

A refreshing outdoor space features a newly designed pool with an attached heated spa, surrounded by a wrap-around sundeck. Several lounge chairs are positioned under palm trees, and a patio umbrella provides shade. A spacious home’s exterior is visible in the background.

5 out of 5 average rating, 41 reviews

Escape to Pool & Beach Paradise!

Unwind in the privacy of your very own tropical oasis in the heart of Naples Park/Vanderbilt Beach area. This sun-filled south facing home showcases a new pool w/heated spa w/wrap around sundeck for the ultimate relaxation. This zen-like 2 BR (Kings), 2 BA retreat is close to Vanderbilt Beach and Mercato is just minutes away! Newly renovated and beautifully decorated. Enjoy your morning coffee from the lanai, the perfect place to contemplate the ultimate decision: Beach or Pool Day?

A living area features a comfortable grey sofa adorned with decorative pillows, complemented by a dark accent chair. A modern coffee table sits centrally, with light streaming in from a nearby window. The space is enhanced by elegant artwork and fans overhead.

4.95 out of 5 average rating, 136 reviews

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

4.98 out of 5 average rating, 146 reviews

A serene pool area features a champagne-style hot tub connected to a shimmering pool, surrounded by a marble deck. A vibrant mural of a sea turtle decorates the wall, while lounge chairs are positioned nearby, inviting relaxation amidst lush tropical landscaping.

Home in Bonita Springs

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

Step into the luxurious 2BR 2BA oasis in the heart of Bonita Springs, FL. It promises a relaxing retreat just a few minutes from the pristine Bonita Beach, restaurants, shops, exciting attractions, and natural landmarks. The stylish design and a rich amenity list will leave you in awe. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Pool, Hot Tub, Swim-Up Bar, BBQ) ✔ Lounge Pool House ✔ Workspace ✔ Smart TVs ✔ Wi-Fi ✔ Parking See more below!

4.93 out of 5 average rating, 111 reviews

Vanderbilt Beach Fun • Pool, Bikes & Beach Gear

Sandbank Cottage – Your Perfect Beach Getaway! ☀️🏡 Enjoy a "stay"cation at Sandbank Cottage, just 1 mile from Vanderbilt Beach and within walking distance to malls, art museums, parks, and more! This family-friendly beach cottage features a private 86-degree heated pool, a lanai-screened porch, and an open-concept living space. The master en suite boasts a king bed, and we provide bikes & beach gear for your adventures! 🌊🚲 NEW & IMPROVED WIFI (Aug 2020)! 🚀No Pet Property

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.

4.99 out of 5 average rating, 153 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.

Popular amenities for North Naples rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 27 reviews

Great Location, Sleeps 8, Heated Pool!

5 out of 5 average rating, 34 reviews

The image features a shimmering heated pool surrounded by a screened-in patio. The inviting outdoor space is accented by comfortable lounge chairs and a scenic view of lush landscaping. A stylish interior is glimpsed through large windows, showcasing a modern aesthetic.

Home in Naples

"Granada"1.5 Miles to the Beach,10 Min to Downtown

4.98 out of 5 average rating, 54 reviews

A shaded outdoor patio area features navy blue cushioned seating and a dining table surrounded by tropical landscaping. A heated pool with a flamingo float is visible through the screened enclosure, alongside a gas grill and lounge chair, creating an inviting space for relaxation.

Home in Willoughby Acres

Naples Retreat with Heated Pool and Fenced Yard

A refreshing concrete pool, measuring 30 feet by 14 feet, is surrounded by a spacious paver patio. Two green lounge chairs sit on the pool's edge, while a small splash pad is also visible. Privacy fencing provides seclusion around the yard.

4.93 out of 5 average rating, 255 reviews

FAMILY FRIENDLY with CRIB**Heated Pool** Naples!!!

A private outdoor area features a newly constructed pool with clear water and a colorful float. Sun loungers are placed around the edge, with a shaded seating area under an umbrella. Lush greenery and a secured fence create a cozy and inviting environment.

4.97 out of 5 average rating, 38 reviews

Huge Game Room•Family Spot•Heated Pool•Near Beach

A private outdoor pool area features a rectangular pool surrounded by a spacious deck. Eight blue lounge chairs are positioned around the pool, and a square spa is integrated into the design. A barbecue grill is situated nearby against a white privacy fence, with tropical plants adding greenery.

4.93 out of 5 average rating, 94 reviews

664 Naples Beach Paradise Private Pool & Spa

4.93 out of 5 average rating, 43 reviews

An enclosed screened patio showcases a heated pool surrounded by tropical greenery. Outdoor furniture is positioned for relaxation, and a gas grill is visible along one side. The open concept allows views into the house, enhancing the inviting, airy atmosphere.

Home in Willoughby Acres

Lush Paradise: Heated Pool, Near Beach, Sleeps 10

4.91 out of 5 average rating, 104 reviews

Entire House with Heated Pool Near the Beach

Apartment rentals with a pool

Apartment in Bonita Beach

A spacious living area features comfortable black leather sofas and a light-colored armchair arranged around a glass coffee table. Large sliding glass doors provide access to the balcony, allowing natural light to fill the room. A textured area rug sits beneath the seating arrangement.

4.92 out of 5 average rating, 122 reviews

Bonita Beach and Tennis 1903

Apartment 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.

4.89 out of 5 average rating, 105 reviews

Beachfront fully equipped apartment

Apartment in Fort Myers Beach

4.83 out of 5 average rating, 118 reviews

Gulf Water Views + 2 bikes, beach gear weekly stay

Apartment in Bonita Springs

A row of modern condos is situated along a sandy beach, with palm trees lining the shore and the Gulf of Mexico visible in the foreground. The sky is partly cloudy, offering a serene coastal view.

4.81 out of 5 average rating, 119 reviews

Oceanview unit. Completely remodeled pool is open!

4.94 out of 5 average rating, 104 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.

Apartment in Park Shore

Lush tropical 1st floor getaway in Naples

4.92 out of 5 average rating, 132 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.

Apartment in Naples

Beautiful Pool 5m to the Beach Downtown & Shopping

Apartment in Bonita Springs

A bright living area features a comfortable seating arrangement with a neutral sofa and a reclining chair. A coffee table is positioned centrally, with a scenic view of the ocean visible through expansive sliding glass doors, leading to a balcony with outdoor seating.

4.97 out of 5 average rating, 148 reviews

Bonita Beach and Tennis 3907 - Ocean Views

Apartment in Bonita Springs

A scenic view showcases Bonita Beach, where the soft sand meets the calm blue waters of the Gulf. Lush palm trees line the beach, with a dining area set back from the shore. A vibrant building is visible, providing options for beachside refreshments.

4.9 out of 5 average rating, 102 reviews

Easy Breezy Too

Other holiday rentals with a pool

5 out of 5 average rating, 13 reviews

Apartment in Naples

Naples Luxurious Resort Retreat with Lazy River

A spacious Master Suite features a king-size bed with decorative pillows and a light grey upholstered headboard. A dark wicker sofa and wooden coffee table are positioned beside large sliding glass doors, leading to a patio area with views of the pool.

4.86 out of 5 average rating, 21 reviews

Mango House with Heated Pool 3 bedrooms 3 baths

4.96 out of 5 average rating, 23 reviews

The living area features a light-colored sofa with decorative pillows, a coffee table, and two lamps. A flat-screen TV is mounted on the wall, accompanied by a dining area with a round table and four chairs. Warm wooden flooring contributes to a welcoming ambiance.

Townhouse in Bonita Bay

Bonita Bay 2 Bed 2 Bath with Beach Shuttle Access

A single-story home is showcased with a light-colored exterior and a metal roof. Lush landscaping surrounds the entrance, featuring tropical plants and a palm tree. A driveway leads to the spacious garage, while blue skies provide a bright backdrop.

5 out of 5 average rating, 41 reviews

767 Naples Villa-Proudly managed by VacayNaples

4.97 out of 5 average rating, 32 reviews

A bright living area showcases comfortable seating arranged around a coffee table. Large windows allow natural light to fill the space, complemented by a bold floral accent wall. The fully equipped kitchen features a generous countertop with seating for four.

Flat in Naples

Beachy Escape: 2BR/2BA w./ Pool, Gym, and Theater

5 out of 5 average rating, 97 reviews

A heated pool is enclosed within a screened lanai, featuring a colorful beach ball floating on the water's surface. Sunlight filters through the mesh walls, illuminating the pool area and surrounding greenery, while lounge chairs are positioned nearby for relaxation.

Cottage in Naples Park

Beach House on pond w/ HEATED pool - sleeps 6

A spacious pool area features a pristine blue pool surrounded by white fencing. Two lounge chairs with soft cushions are positioned at the pool's edge, accompanied by colorful, woven side tables. Lush greenery is visible in the background, enhancing the serene atmosphere.

5 out of 5 average rating, 14 reviews

The Pop Hauz - Large Pool Home+MotherInLaw Suite