Holiday rentals with outdoor seating in Naples

4.99 out of 5 average rating, 142 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.

An inviting collage showcases various areas of the Naples Holiday House. Bright outdoor seating is paired with an umbrella, while the living space features comfortable seating and coastal decor. A cozy dining area invites meals al fresco, and serene beach views complete the relaxing atmosphere.

4.95 out of 5 average rating, 198 reviews

Home Close To Beach & Downtown Naples

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

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, 101 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.

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.

4.99 out of 5 average rating, 134 reviews

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

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 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, 164 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.

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, 132 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.

5 out of 5 average rating, 181 reviews

A bright living area is presented with a cozy sofa adorned with colorful cushions. A stylish coffee table sits on a soft area rug. A staircase leads to the loft bedroom, while two woven pendant lights hang from the ceiling, enhancing the space's beachy vibe.

Tiny home in Pelican Bay

BEACHYVibes TINY House Pickleball Ct Mile to Beach

Located less than one mile from the beach in the center of the city hustle, the minute you step inside our “Tiny House" the beachy vibe gently reminds you of why you came! The 12' living room makes the 400 sq ft space feel more expansive. Sailor’s knot rope tied around anchored cleats create a banister railing to the 6’2” spacious loft bedroom. Nestled below an eat-in kitchen and full bath. The stand alone new construction has a private entrance and luscious outdoor private patio.

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, 103 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..

A simple bedroom features a spacious bed with a light quilt. A nightstand with a lamp and an alarm clock is positioned beside the bed. A small dresser is visible, and natural light enters through the window, which is dressed in light curtains.

4.98 out of 5 average rating, 269 reviews

Bear Necessities - 1 Bdrm 1 Bthrm w/Kitchen/Lvrm

Relax and enjoy Florida indoors and outdoors in this "mini-apartment". You can watch for roaming wildlife and enjoy the tall pine trees, palm trees, and cypress trees from the patio. The "mini-apartment" is within walking distance of the canal where you can go bird watching and possibly see other wildlife. The apartment is outside of the busy hustle and bustle of the city but within driving distance of the beach. There are several restaurants with indoor or outdoor dining options.

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.

4.93 out of 5 average rating, 155 reviews

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.

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.

4.93 out of 5 average rating, 14 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, 111 reviews

The WaterSun Oasis - Luxury Private Pool & Spa

A clear blue pool features a spa area, bordered by decorative stone. Two lounge chairs are positioned alongside the water, offering a relaxing area. A dining table with multiple chairs is visible in the background, with a privacy fence and lush greenery completing the serene outdoor setting.

4.97 out of 5 average rating, 213 reviews

Last Minute Deals! Walk to beach! Jacuzzi & Pool

A spacious covered porch offers a view of a tranquil lagoon surrounded by tropical foliage. Comfortable outdoor seating is complemented by a small table, while vibrant flowers are arranged in a vase. Sunlight reflects off the water, enhancing the outdoor ambiance.

4.96 out of 5 average rating, 165 reviews

Tropical Cottage by the Sea- your own private home

Superhost

The exterior of a two-story house is framed by palm trees, showcasing a welcoming entry with steps leading up to a spacious deck. Lush green foliage surrounds the home, providing a tropical feel beneath a clear blue sky.

4.86 out of 5 average rating, 142 reviews

#Closest2Beach - 3BD/3BA Oasis by RITZ BEACH GOLF

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, 20 reviews

Modern Home in Naples w/ Heated Pool

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, 35 reviews

Mediterranean Inspired Villa with Private MiniGolf

A heated pool is surrounded by a manicured landscape, featuring reclining lounge chairs positioned for relaxation. A playful water slide rests at one end of the pool. Complimenting the scene, a clear blue sky and fluffy white clouds create a bright atmosphere.

4.94 out of 5 average rating, 49 reviews

NEW Villa Mare LUX Sleeps 12|Heated Pool|2 Masters

Apartment rentals with outdoor seating

5 out of 5 average rating, 12 reviews

Tropical Dream 2BR/2BA w./ Pool, Gym, and Theater

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, 243 reviews

Private&Romantic. Walk to Beach; Unwind in Jacuzzi

4.95 out of 5 average rating, 115 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

A cozy living area is presented, featuring a sectional sofa in a neutral tone and a round wooden coffee table. A wall-mounted television sits above a simple white fireplace. Natural light enters through a window, with a decorative mirror reflecting the space.

4.76 out of 5 average rating, 151 reviews

Bayshore Getaway

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, 112 reviews

Beach/Sunset Bay/Sunrise Relax/Island Living

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.

4.98 out of 5 average rating, 112 reviews

Cozy 1 Bedroom Villa - Beautiful Naples, Florida!

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.

4.89 out of 5 average rating, 106 reviews

13 Downtown Near Beach Free Heated Pool and Spa

4.93 out of 5 average rating, 162 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.

Condo rentals with outdoor seating

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, 165 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

The outdoor patio features two wooden lounge chairs with decorative cushions positioned around a small wooden table. Lush greenery and trees provide natural shade, while a picnic table is visible in the background, inviting outdoor gatherings.

4.92 out of 5 average rating, 124 reviews

5th Ave & Beaches 10 Minutes Away! 2 BD/2 BA

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

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 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

4.97 out of 5 average rating, 144 reviews

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.

Condo in Bonita Springs

Bonita Beach and Tennis 3907 - Ocean Views