Holiday rentals with a pool in Naples

5 out of 5 average rating, 100 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🏖️

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, 108 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.

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, 207 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.

Superhost

5 out of 5 average rating, 3 reviews

*NEW Vanderbilt Drive - Dream Vacation Home*

Relax in this 4 bedroom + Pool house beachside retreat on coveted VANDERBILT DRIVE, just 1 mile from either Wiggins Pass, Vanderbilt Beach, and Mercato. Enjoy this newly renovated home with luxury finishes, quality furniture, and coastal decor. Located on Vanderbilt Dr! Walk out the front door and go for a jog, bike ride, or a coffee stroll. Come see why we maintain Superhost status across all properties and experience another one of our thoughtfully furnished and decorated retreats.

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, 135 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.

The image captures a luxury villa with a heated pool and spa, surrounded by palm trees. Lounge chairs and umbrellas are positioned around the pool deck, providing a relaxing area. An outdoor kitchen is visible, featuring a BBQ grill and refrigerator, ideal for al fresco dining.

4.98 out of 5 average rating, 106 reviews

Shiny Clean •Htd Pool •SPA •Sunny •BBQ •Bike2Beach

🌟Shiny clean, sunny, resort-style beach home 🪟4BR, 4 luxury bathrooms, poolside private shower ☀️All day sun pool deck w loungers/sun bed 🏊Heated pool(NO FEE) SPA/Hot tub ⛱️Beach gear, pool toys, full-size game arcade, Foosball 🏝️Close 2 beach. 4 beach bikes. 6 minute bike ride to beach 📶Outdoor movie theater, Instagrm wall, 5 LED TVs, 1Gbps Wifi, remote office setup 👨‍🍳Fully equipped chef's kitchen w bakeware, BBQ grill Washer/dryer, 2-car garage 🧳Ultra luxury awaits..

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, 151 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.

5 out of 5 average rating, 17 reviews

New! Blue Haven-Heated Salt Pool/Spa,Walk to beach

Blue Haven Haus is a professionally designed coastal retreat in Naples Park. The spacious interior features 3 bedrooms, including a primary suite with a king bed and en-suite bath, a 2nd king bedroom, a 3rd bedroom with two twin beds, and a full guest bath with a bathtub. Outfitted with a heated saltwater pool & spa, Smart TVs, beach gear & games. Luxurious touches meet laid-back style, steps from Vanderbilt Beach & Ritz-Carlton. House attendant on-call during your stay!

An outdoor kitchen and bar area is illuminated with soft lighting, showcasing a grill and ample counter space. The saltwater pool features calming purple lights, while seating stools are placed nearby, surrounded by lush tropical landscaping for a serene atmosphere.

4.97 out of 5 average rating, 114 reviews

The WaterSun Oasis - Luxury Private Pool & Spa

The WaterSun Oasis is a 3 bedroom, 2 1/2 bath home, perfect for family or friends to get away. Less than one mile from Vanderbilt Beach, this high-quality private house, equipped with a top-notch outdoor pool area, is packed with best-in-class amenities to set your experience apart from others. Located just 30-minutes from RSW International Airport and surrounded by multiple beaches, restaurants, shopping centers, night life and more. Book your stay today!

An inviting outdoor space features a heated pool beside a hot tub, while comfortable seating arrangements are visible. A dining area is adorned with modern green chairs, and sliding doors provide access to the interior. A pink inflatable flamingo adds a playful touch to the pool area.

4.96 out of 5 average rating, 118 reviews

2 Mstrs w Kings, Pets, Queen ensuite, hot tub, htd

The perfect home for a beach vacation just a 6 min bike ride to the beach and 2 master suites with king beds, walk-in closets, TVs, and private baths, 1 ensuite with a Queen bed, and the 4th bedroom with twin beds. Even a pool bath and outdoor shower! A large chef's kitchen with all Bosch appliances. Every space is designed for a group of 8-10 to gather. Bikes, towels, beach chairs, toys are all included! Great for large groups of 8-10 to gather and enjoy.

Popular amenities for Naples rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 60 reviews

A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.

Home in Cape Coral

Coastal Cowgirl - Heated Pool

4.92 out of 5 average rating, 25 reviews

Great Location, Sleeps 8, Heated Pool!

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.

5 out of 5 average rating, 33 reviews

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

5 out of 5 average rating, 15 reviews

An aerial view of the serene waterfront property showcases a south-facing pool and hot tub, framed by a screened-in lanai. The spacious dock features various seating arrangements, including loungers and a shaded area, all set against the tranquil canal backdrop, enhancing the outdoor experience.

Home in Cape Coral

Pool, Hot Tub, Kayaks, Dock & Canal w/ Gulf Access

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, 13 reviews

The Marquee of Naples

An enclosed lanai features comfortable seating arrangements, including a wicker coffee table and two upholstered chairs positioned on a patterned rug. A wall-mounted flat-screen TV is visible. Beyond the lanai, the pool and outdoor lounging area can be seen, surrounded by greenery.

5 out of 5 average rating, 20 reviews

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

An open-concept living area features a spacious sectional sofa with decorative cushions. A dining table with elegant chairs is visible, along with a modern kitchen displaying dark cabinetry, stainless steel appliances, and a large island with bar seating. Ceiling fans and recessed lighting enhance the ambiance.

4.93 out of 5 average rating, 88 reviews

Naples Home-Min to beach,shops,dining. Heated Pool

5 out of 5 average rating, 14 reviews

Luxe Sunset Splash, Epic Pool, Hot Tub, Beaches

Apartment rentals with a pool

A resort-style pool is surrounded by tropical palm trees, with waterfalls cascading from built-in rocky features. The clubhouse is visible in the background, featuring light-colored siding and large windows. Lounge chairs are scattered around the pool area, inviting relaxation.

4.93 out of 5 average rating, 164 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

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.

4.88 out of 5 average rating, 104 reviews

Beachfront fully equipped apartment

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

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.

4.8 out of 5 average rating, 116 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, 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

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

An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.

4.99 out of 5 average rating, 146 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Other holiday rentals with a pool

4.98 out of 5 average rating, 98 reviews

A dining area features a long wooden table set for eight, surrounded by sleek black chairs. A sideboard holds decorative items, and large windows provide a view of the outdoors, allowing natural light to enhance the minimalist decor.

Villa in Cape Coral

Luxury Canalfront Pool Retreat w/ Upscale Finishes

A heated swimming pool is surrounded by lush greenery, featuring palm trees and colorful plants. Several lounge chairs are positioned around the pool, and a blue umbrella provides shade. A waterfall feature enhances the tranquil setting.

5 out of 5 average rating, 36 reviews

Lovely 2-bedroom condo with pool

4.97 out of 5 average rating, 31 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

An outdoor dining area is highlighted by a large wooden table surrounded by woven chairs. Pendant lights hang above, casting soft illumination. A swimming pool with clear water is visible through a screened enclosure, complemented by lush greenery in the background.

5 out of 5 average rating, 42 reviews

Mediterranean Inspired Villa with Private MiniGolf

4.98 out of 5 average rating, 44 reviews

An open living area features a spacious arrangement of light-colored furniture, including a large leather sectional and armchairs. A modern fireplace and flat-screen TV are positioned on a textured feature wall. Natural light floods the space through expansive glass doors that overlook the pool area.

Home in Cape Coral

Villa Sunset Serenade II

4.94 out of 5 average rating, 83 reviews

Naples Oasis: Cozy 2B/2BA Home w/Pool 10 Min Beach

5 out of 5 average rating, 40 reviews

A spacious screened lanai features a private pool surrounded by lounge chairs. A BBQ grill is positioned nearby, and a glimpse of the indoor living area is visible through large glass doors. Lush greenery offers a natural backdrop to this relaxing outdoor space.

Villa in Naples

Salt Pool Oasis: 5 Miles to Beaches (4BD/3BA)

An open-concept living room features a spacious leather sectional sofa, a round coffee table with greenery, and a large flat-screen Smart TV displaying a tropical beach scene. Sunlight brightens the space, complemented by a ceiling fan and decorative potted plants.