Holiday rentals with a pool in Glades

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.

4.96 out of 5 average rating, 28 reviews

A marina is depicted with multiple boats moored along a calm waterway. Clear blue skies reflect on the water's surface, while palm trees line the background, adding greenery to the scene. The image conveys a sense of tranquility and leisure.

Flat in Naples

Serenity Studio: Waterfront & Wildlife Everglades

Steps away from your studio, sit by the bay to watch manatees, dolphins, and schools of fish. Drive down the road to explore Everglades boardwalks and state parks. Go shelling at the world renowned Ten Thousand Islands, just a 20 minute boat ride from the onsite marina. Relax at the spatial 9 foot pool. Bring your racquets to play tennis or pickleball. Check out the golf courses minutes down the road. Take a break and unwind at this peaceful oasis! Just a short drive from Marco Island amenities.

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.

A modern living area is highlighted by a spacious sofa and two accent chairs, complemented by a large flat-screen TV. Natural light pours in through sliding glass doors, which open to the balcony. A dining table sits in the corner, enhancing the open layout.

5 out of 5 average rating, 130 reviews

Beach Across the Street! Balcony in the ❤️of Marco

A modern 1 bed 1 bath condo nestled in the heart of Marco Island and packed with everything you need for an unforgettable and effortless trip. Enjoy the convenience of beach access right across the street and JW Marriott a block away! Perfectly located on the main strip with popular restaurants like Da Vinci's and Marco Prime, shops, grocery stores, and major convention centers just down the road. Wind down your day watching breathtaking western exposure sunsets from your own private balcony...

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 bright living area is furnished with comfortable sofas and a coffee table. Light blue walls enhance the spaciousness, while a ceiling fan circulates air. A large television is mounted on the wall, and glass doors offer a view of the outdoor pool area.

4.97 out of 5 average rating, 151 reviews

Beachy Chic house Free bikes/SUPs Less mile beach

Beautifully renovated beach house walking or short bike ride to everything you need to enjoy Marco Island's beautiful weather. New, designer furnishings decorated in beachy chic. 3 bed, 2.5 bath. Great location 7/10 mile from Tigertail beach. 3 min bike ride or short walk to beach. Beautiful large pool and screened lanai for al fresco dining. Walking to many restaurants. Everything you need for fun at in the sun: Bikes, umbrella, cooler, beach towels. Enjoy paradise at your own pool home!

4.93 out of 5 average rating, 14 reviews

A bright living space is characterized by high vaulted ceilings and natural light filtering through the windows. A cozy, dark sofa is paired with a small dining table and two stools. Decorative accents include a lamp and a patterned table runner, enhancing the inviting atmosphere.

Cabin in Everglades City

Everglades Fishing Cabin

Escape to the heart of the Everglades in this serene waterfront cabin. This 1 bedroom 1 bath cabin is designed for anglers and nature lovers, with a private dock, fish cleaning station, and plenty of space to store your gear. No boat? No problem! Enjoy activities like shoreline fishing, air boating , kayaking or kick back and float in the heated pool. Whether you're a seasoned fisherman or just looking for a peaceful escape, this cabin offers the perfect blend of adventure and relaxation.

4.89 out of 5 average rating, 150 reviews

A well-maintained entrance is framed by a landscaped area featuring a pink flowering tree and small shrubs. The pathway, made of pavers, leads to an archway, while a garage door is visible to the right, complementing the modern architectural style.

Guest house in Ave Maria

Cozy, private two-room suite

A cozy, modern space in a family-friendly town. This two-room apartment with private entrance is in walking distance of the University, restaurants, shops and a Publix grocery store. Equipped with kitchenette. Smart tv in living area. A queen-sized bed with a full bathroom and a walk-in closet. Twin air mattress and Pack ‘n play available. Amenities in town include a waterpark with waterslides and swimming lanes, playgrounds, walking and bike trails, tennis and pickleball courts.

Superhost

A two-story house features a light blue exterior with multiple windows. The inviting pool, illuminated in green, is surrounded by a paved patio. Comfortable lounge chairs and a dining table can be seen adjacent to the pool, providing ample space for relaxation and outdoor dining.

Holiday home in Collier County

4.82 out of 5 average rating, 22 reviews

4-bedroom house with pool steps from the dock!

Bring your boat and experience Big Cypress, the Everglades and 10,000 islands in luxury! We have parking for 6+ cars and a carport for your boat or kayak trailer. You can also have access to a dock with a lift upon request. All beds have extremely comfortable mattresses and smooth bamboo sheets that let you sleep like you are at home. Bring the whole family for tons of fun in the sun. Relax with open living space inside or lounge by the pool. Guaranteed not to disappoint!

A screened-in outdoor area features a clear blue inground pool alongside a jacuzzi, both surrounded by stone pavers. Lush greenery is visible beyond the enclosure, providing a serene backdrop. Comfortable seating awaits for relaxation in this private oasis.

4.93 out of 5 average rating, 136 reviews

Venetian Photoshoot - La Dolce Vita

Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

Apartment in Everglades City

A spacious building with a modern design is flanked by palm trees under a clear blue sky. The entrance is marked by a covered area, with a parking lot visible in the foreground, offering ample space for vehicles.

4.81 out of 5 average rating, 199 reviews

Everglade Isle Palms Condotel w/ Pool & Boat Ramp

It’s island time! Welcome to your home base for exploring the Florida Everglades. With all the comforts of home, our Condotel will be your ideal vacation spot. Explore Everglades National Park, the 10,000 islands, airboat tours, and more! Bring your boat or rent one for saltwater, brackish, & freshwater fishing- all from this unique & pristine area. Located in the heart of town, you’ll be in walking distance of several restaurants, ice cream parlors, and the grocery store.

The illuminated pool glistens in a tranquil setting, adorned with floating yellow lily candles. Lounge chairs with striped towels are positioned beside the water, while soft lights provide ambiance around the area, creating a serene space for relaxation.

4.97 out of 5 average rating, 143 reviews

Top-rated luxury pool home in prime location

💰No nickel & diming — AirBnb & cleaning fees in nightly rate! 🏠Newly renovated & professionally designed 👙Amazing pool and outdoor kitchen (including grill, pizza oven, fridge)! 🏖️4 mins to beach 🌊Beach chairs, umbrellas, beach wagon & bikes 🐶Low pet fee; we love our 4-legged guests! ✅Fully stocked chef’s kitchen 🛌🏽Super comfortable beds for ultimate comfort and sleep 💻 High speed internet with dedicated workspace 😊24/7 local & professional host support!

Popular amenities for Glades rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An inviting outdoor space showcases a curvy swimming pool surrounded by several sun loungers. Lush palm trees provide shade, while views of the canal and dock area are visible in the background, creating a serene waterfront atmosphere.

5 out of 5 average rating, 21 reviews

Total Haven on Marco Island

4.98 out of 5 average rating, 113 reviews

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.

Home in Naples Park

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

An aerial view captures the home's screened-in patio alongside a peaceful canal, framed by palm trees. A wooden boat dock extends into the water, featuring lounge space. Lush greenery enhances the serene atmosphere, while the home’s roof is visible, showcasing a warm, inviting design.

5 out of 5 average rating, 42 reviews

Book Your Holiday Stay in Marco Island

An expansive lanai features a shimmering pool with a waterfall-edge spa and in-pool loungers. The outdoor space is surrounded by a screened enclosure, providing views of well-kept greenery. A comfortable seating area and dining space are visible in the background, enhancing the outdoor living experience.

5 out of 5 average rating, 23 reviews

Pool Home Minutes to the Beach

4.97 out of 5 average rating, 203 reviews

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.

Home in Naples Park

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

A screened enclosure surrounds a private saltwater pool, featuring a clear water surface and two sun loungers positioned at the edge. Large windows in the background reveal a view of a spacious living area, enhancing the indoor-outdoor connection.

4.94 out of 5 average rating, 17 reviews

3 bed home w/ beautiful pool in tropical paradise

A modern single-story home is showcased with a sleek facade and an inviting entryway. A well-maintained driveway leads to a garage, with green landscaping and carefully arranged plants adorning the front. Large windows allow natural light to fill the interior space.

4.98 out of 5 average rating, 96 reviews

Flamingo Paradise 4 min walk from Beach Access.

5 out of 5 average rating, 24 reviews

Paradise Point with Private Pickleball Court

Apartment rentals with a pool

A tranquil waterfront view captures the shimmering water reflecting hues of orange and pink during sunset. Several boats are docked at a nearby marina, framed by lush palm trees and the soft glow of lights along the pathway.

4.98 out of 5 average rating, 107 reviews

Riverside Paradise!

An open living area features a comfortable, light-colored couch paired with two wooden chairs. A flat-screen TV hangs above a modern electric fireplace, which adds warmth. Large glass doors provide a view of the waterfront, while soft curtains frame the serene scene.

4.95 out of 5 average rating, 183 reviews

Amazing New Seaside Condo-5 fl View -Best Building

Aerial view showcases a beachfront condo complex with multiple buildings surrounded by palm trees. The sandy beach and ocean are visible in the background, with lounge chairs arranged along the shore. A heated pool and landscaped areas can be seen within the property, contributing to a serene coastal setting.

4.94 out of 5 average rating, 168 reviews

Marco Beach Ocean Resort 707

4.9 out of 5 average rating, 164 reviews

A serene beach scene captures the golden hues of sunset over calm waters. Several wooden posts are visible in the sand, while a figure holds a child on one of the posts. Another individual is seen photographing the moment, adding a sense of warmth to the atmosphere.

Apartment in Old Naples

Studio- Olde Naples, 2 blocks to beach Studio unit

Apartment in Fort Myers Beach

4.82 out of 5 average rating, 113 reviews

Gulf Views & Sunsets | Estero Beach Tennis 206C

A serene beach scene captures a person walking along the shoreline. Soft white sand meets gentle turquoise waves under a bright blue sky dotted with clouds. The horizon stretches into the distance, creating a sense of openness and tranquility.

4.91 out of 5 average rating, 174 reviews

Seahorse, By The Beach

4.91 out of 5 average rating, 120 reviews

Beachfront condo. Stunning views. Amazing sunsets!

4.91 out of 5 average rating, 163 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

Other holiday rentals with a pool

The open living and dining space is illuminated by natural light, featuring a neutral palette and modern furnishings. Floor-to-ceiling windows provide unobstructed views of the ocean, while a cozy seating area and a dining table invite relaxation and enjoyment of the surroundings.

5 out of 5 average rating, 17 reviews

November special: Beachfront unit w/amazing views

5 out of 5 average rating, 13 reviews

An aerial view of a large outdoor pool surrounded by palm trees and lounge chairs. Umbrellas provide shade over several seating areas, and vibrant landscaping enhances the tropical setting, complementing the pool's unique shape and inviting blue water.

Flat in Naples

Green Links Retreat

A single-story home is framed by lush greenery and colorful landscaping. A welcoming entryway is visible, featuring arched windows and a shaded porch. The driveway leads to a garage, with palm trees swaying gently in the breeze under a clear blue sky.

5 out of 5 average rating, 38 reviews

NEW Island Paradise With Private Heated Pool/Dock

4.95 out of 5 average rating, 41 reviews

A private balcony is showcased with a wooden table and two woven chairs, providing a view of palm trees and sunset colors in the sky. A ceiling fan is mounted above, and a decorative rug adds warmth to the space.

Flat in Marco Island

Best Waterfront Retreat 406

Sun loungers with colorful towels are positioned beside a private heated pool, featuring a pink flamingo float. A fruit platter and drinks are arranged on a tray, with lush greenery visible through the screened enclosure, offering a tranquil outdoor retreat.

4.91 out of 5 average rating, 46 reviews

Heated Pool | EV Charger | Minutes To The Beach

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

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,