Holiday rentals with outdoor seating in Naples

A welcoming living area features a white sectional sofa adorned with neutral pillows. A glass-top coffee table sits at the center, showcasing a decorative centerpiece. Large windows provide a view of the lush garden and private pool area through bright, natural light.

5 out of 5 average rating, 8 reviews

Paradise in the Park - Heated Pool

Welcome to your ideal Naples, Florida retreat! This charming vacation home offers everything you need for a perfect getaway. Nestled in a beautifully landscaped setting, the property features a private, heated saltwater pool. Located just a short bike ride away from the pristine Naples beaches. Shopping and dining options nearby. ***This is a 5 star property. I switched superhosts & my reviews did not transfer. I have guest coming back for 4th & 5th time. It's as great as it looks in photos

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.

Condo in Park Shore

Lush tropical 1st floor getaway in Naples

Whether you're looking for a family-oriented or quiet, romantic vacation, we've got you covered! Our unit is tucked away at the south end of our complex where the trickle of the waterfall outside your lanai is the perfect backdrop to enjoying your morning coffee or perhaps a vacation cocktail! Our unit is completely remodeled in an updated coastal-chinoiserie style that is a combo of classic and contemporary, but also livable (we have two young children). Perfect backdrop to your time in SW FL!

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, 136 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 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.

Superhost

A modern living area features a light-colored sofa draped with a textured throw. A glass coffee table sits in front, and large windows allow natural light to illuminate the space. Elegant decor includes a console table and a stylish wall mirror.

4.95 out of 5 average rating, 157 reviews

Private Paradise | Large, Peaceful Studio w Patio

This modern coastal retreat is a complete studio apartment with a direct, private entrance: Private outdoor sitting area w/ umbrella Smart TV w/ Netflix, Amazon TV, Disney+ Queen sized bed w luxury mattress Dresser & closet Workspace w/ wireless charging Walk-in marble tiled shower w/ full vanity Incl. Bath Amenities Kitchenette w/ fridge & freezer Keurig w/ complimentary coffee Induction cooktop Microwave Toaster Oven/Air Fryer Washer/Dryer Beach Towels, Chairs, Umbrella Parking for one car

A spacious stilt home features large windows that provide ample natural light. An outdoor deck with seating overlooks the canal, surrounded by palm trees. A boat dock is visible alongside smooth stone pathways leading to the house, creating a tranquil waterside setting.

4.99 out of 5 average rating, 166 reviews

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

4.94 out of 5 average rating, 70 reviews

Luxe Oasis: putting green, fire-pit, near beach

Welcome to your Naples Park escape! This modern 2-bedroom, 2-bath home blends comfort and fun with everything you need for a Florida getaway. Relax in the large private heated pool, practice your swing on the turf putting green, or unwind by the fire pit at night. With 4 complimentary beach bikes, BBQ grill, and optional concierge services, your group will enjoy the perfect mix of relaxation and adventure—just 1 mile from white-sand beaches and minutes to Mercato’s dining and nightlife.

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.

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, 150 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.

4.99 out of 5 average rating, 292 reviews

A cozy living area is highlighted with a light sofa and green accent chair, complemented by a glass-topped table. A large vibrant palm tree artwork adorns the wall, while a staircase leads to the upper sleeping area. Natural light fills the space through nearby windows.

Tiny home in Pelican Bay

TINY House BIG Living Pickleball Ct Mile to Beach

Located less than one mile from the beach in the center of the city hustle, step inside our “Tiny House" and ease into beach life! Gallery white walls, oversized art and 12' living room ceiling make the 360sf space feel more expansive. Sailor's knot rope tied around anchored cleats create a banister railing to the 5'6" loft bedroom nestled above a 6'2" kitchen and bathroom. The private entrance was designed for absolute privacy.

A private backyard features a heated in-ground pool and spa, surrounded by lush greenery. Four lounge chairs sit alongside the pool, inviting relaxation. A floating swan pool float adds a playful touch. The covered lanai offers shade and is perfect for outdoor gatherings.

5 out of 5 average rating, 32 reviews

Gulf Haven Hideaway: Naples 4BD Oasis - Pool + Spa

Gulf Haven Hideaway - Brand New Luxury Retreat Welcome to Gulf Haven Hideaway, a stunning 2024-built luxury home in Naples, FL! Located in the quiet Naples Park neighborhood, this 4-bedroom, 4.5-bathroom retreat is the perfect blend of modern design, comfort, and coastal charm. Just minutes from the beach and the vibrant Mercato shopping & dining complex, it’s ideal for families and groups looking to enjoy the best of Naples.

A backyard oasis features a heated pool surrounded by tropical landscaping. Lounge chairs are arranged around the pool, and a pink inflatable float adds a pop of color. An umbrella shaded seating area is visible nearby, contributing to the inviting outdoor space.

4.95 out of 5 average rating, 175 reviews

529 Whispering Palms Oasis | Private Heated Pool

NEW HEATED POOL creates your backyard Oasis! This 3 Bedroom, 2 Bathroom spacious home will book up fast. Located in the popular Naples Park neighborhood this home is between 2 world class beaches, Vanderbilt Beach & Delnor Wiggins Pass Beach. Mercato Shopping & Dining District is just a a quick 5 minute drive & Downtown Naples is just 15 minutes. 2 bicycles available for you to be at the beach in 5 minutes.

Popular amenities for Naples outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

The exterior of the two-story luxury retreat is showcased, featuring modern architecture with a clean facade. Surrounding the private pool, lush greenery and vibrant landscaping enhance the ambience. A sunset sky casts warm hues over the scene, providing a serene backdrop.

4.94 out of 5 average rating, 16 reviews

Naples Amore | Pool, Playground, Grill, EV, Arcade

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

4.93 out of 5 average rating, 67 reviews

A spacious open-concept living area is showcased, featuring a modern kitchen with an island and sleek cabinetry. Large glass doors provide abundant natural light and views of the outdoors. Rustic wooden beams contrast with the contemporary décor, highlighting both elegance and comfort.

Home in Cape Coral

AquaLux Smart Home

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, 32 reviews

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

An inviting outdoor area features a heated pool surrounded by a screened enclosure. A floating pool toy is present in the water, while lounge chairs are positioned nearby. Sliding doors lead to the interior living space, enhancing the seamless indoor-outdoor connection.

4.94 out of 5 average rating, 18 reviews

Families-private heated pool & hot tub-pickle ball

5 out of 5 average rating, 6 reviews

Home in Willoughby Acres

Modern Naples Retreat w/Pool & Hot Tub Near Beach

A collage of images showcases the property's features, including a spacious interior with a living area, a heated saltwater pool and spa, two private pickleball courts, and a lush, green exterior. Each element highlights the abundant space and recreational opportunities available.

4.96 out of 5 average rating, 83 reviews

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

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

Apartment rentals with outdoor seating

Superhost

A single-story home features a light exterior with a welcoming front entrance and a garage. Lush palm trees and manicured shrubs frame the property, while a clear blue sky enhances the peaceful setting.

Apartment in Naples Park

4.88 out of 5 average rating, 244 reviews

Private&Romantic. Walk to Beach; Unwind in Jacuzzi

4.95 out of 5 average rating, 123 reviews

A modern bathroom features sleek tile walls and a glass shower enclosure. A floating vanity is positioned next to a round mirror, and a compact toilet is included. Decorative elements include a small plant and textured bath mat, enhancing the space's contemporary design.

Apartment in Fort Myers

Blackstone Villa

Apartment in Bonita Beach

A quaint outdoor seating area features white Adirondack chairs arranged around a circular table. Lush greenery surrounds the space, while a serene waterfront is visible in the background, showcasing a calm waterway lined with palm trees and distant homes.

4.97 out of 5 average rating, 113 reviews

Beach/Sunset Bay/Sunrise Relax/Island Living

4.97 out of 5 average rating, 118 reviews

A light-filled living area features a spacious beige sofa and a comfortable lounge chair. A coffee table sits in front, with decorative items placed on it. A dining table for four is visible, accompanied by abstract wall art and soft lighting from ceiling fans.

Apartment in Naples

Cozy 1 Bedroom Villa - Beautiful Naples, Florida!

4.89 out of 5 average rating, 106 reviews

A private pool is surrounded by a spacious deck, featuring two white lounge chairs positioned under a large umbrella. Lush greenery and palm trees are visible in the background, complemented by a fenced yard that adds to the secluded atmosphere.

Apartment in Naples

13 Downtown Near Beach Free Heated Pool and Spa

4.99 out of 5 average rating, 134 reviews

A sunset view features a wooden pier stretching over waves, with silhouettes of people gathering at the end. Warm hues of orange and yellow illuminate the sky, creating a serene backdrop against the gently rolling ocean.

Apartment in Naples

Beach Vacation Getaway

4.93 out of 5 average rating, 165 reviews

A bright and airy room features a spacious bed adorned with decorative pillows. A large window allows ample natural light and offers a view of the waterfront. Light-colored walls and furnishings create an inviting ambiance, enhancing the serene atmosphere of the space.

Apartment in Cape Coral

Suite with lake view.

Superhost

Apartment in Bonita Springs

4.89 out of 5 average rating, 137 reviews

1st Floor Freshly Updated Kit W&D 3 Miles to Beach

Condo rentals with outdoor seating

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.

4.88 out of 5 average rating, 104 reviews

Beachfront fully equipped apartment

A wooden pier extends into the ocean, supported by numerous vertical posts. Two structures with thatched roofs are visible at the end of the pier. Gentle waves lap at the shoreline, reflecting the sunlight, with a clear sky above.

4.95 out of 5 average rating, 168 reviews

Sea Shell Villa 1

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

A personal patio space features four wooden lounge chairs arranged around a small table. Lush greenery and palm trees surround the area, complemented by a serene view of the pond and a clear blue sky above.

4.95 out of 5 average rating, 118 reviews

2.5 miles to Beaches & 5th Ave

A tranquil evening scene features palm trees silhouetted against a colorful sunset sky. Reflections of dusky hues are visible on the calm water, while lights from nearby structures softly illuminate the surroundings.

4.89 out of 5 average rating, 101 reviews

The Perfect Resort for the Vacation You Want

4.93 out of 5 average rating, 109 reviews

A bright living and dining area features a white dining table set with blue accents. A comfortable light-colored sofa is positioned nearby, inviting relaxation. Large sliding glass doors provide views of the balcony and surroundings, allowing natural light to fill the space.

Condo in Park Shore

Park Shore Resort Beautiful Top Floor 2 Bed 2Bath

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, 47 reviews

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

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.