Holiday rentals with a pool in Mary Esther

A generous balcony features a round table surrounded by four striped chairs, offering ocean views. Two blue lounge chairs are positioned beside the table. The expansive space allows for comfortable relaxation while overlooking the beach and turquoise waters.

4.93 out of 5 average rating, 288 reviews

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA

Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the BEACH. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.

4.94 out of 5 average rating, 202 reviews

Whispering Getaway, Heated Pool, Premier Game Room

Experience Coastal Comfort at Whispering Paradise Welcome to your premier getaway in beautiful Navarre, FL! This meticulously maintained 4-bedroom, 2-bathroom retreat is the perfect sanctuary for families and groups seeking both relaxation and adventure. Highlights of Your Stay: Private Amenities: Enjoy a secluded, heated pool and a fully equipped, climate-controlled game room. Modern Conveniences: Features include self check-in, 1000 Mbps Fiber Wi-Fi, stainless steel appliances, and onsite

The outdoor pool is framed by a screened enclosure, providing clear views of the tranquil bay waters. Comfortable lounge chairs are positioned beside the pool, and potted plants add a touch of greenery. A wooden dock extends into the bay, enhancing the serene ambiance.

4.97 out of 5 average rating, 192 reviews

East Bay Hideaway — A Private Waterfront Escape

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

Condo in Fort Walton Beach

A serene twilight view captures the sky filled with clouds reflecting subtle shades of orange and blue. The marina lights twinkle along the water's edge, while the horizon highlights an array of colors as day transitions into night.

4.97 out of 5 average rating, 217 reviews

Waterfront Studio • Santa Rosa Sound • Sunsets

Enjoy breathtaking views of the Santa Rosa Sound and marina from your private top-floor balcony in this waterfront studio. Whether you're sipping coffee at sunrise or watching vibrant sunsets each evening, this spot delivers unforgettable costal charm in a quiet, peaceful setting. Perfect for couples or solo travelers, the studio features a full bath with tile shower, well-equipped kitchenette and sparkling pool. Gulf beaches are a just a short drive away. Free parking and easy self check-in.

The outdoor area features a non-heated swimming pool surrounded by a concrete patio. A small table with chairs is positioned nearby, offering a space for relaxation. Lush greenery provides shade, and a seating area with chairs is visible on the lawn.

4.89 out of 5 average rating, 339 reviews

#1 4BR HUGE PET Friendly Home Away from Snow!

Modern house w/ 2 master bedroom suites with own bathroom and 2 additional rooms sharing a bathroom. Welcome to the emerald coast paradise! You have the best of both worlds, Okaloosa island and the night life are only less than 3 miles away, the beautiful sugar sand beaches are only couple miles away, and you have your own pool (non-heated) in the backyard if you just want to relax and get your tan on! Shopping outlets are near by! Great restaurants around to choose from!

A private pool is enclosed by a screened-in structure, allowing for a comfortable swimming experience. Colorful pool floats and lounge items are placed nearby, with a bright blue water surface reflecting light. Lush greenery is visible beyond the pool area, offering a sense of privacy.

4.92 out of 5 average rating, 302 reviews

Touch of Madagascar-Whole House

Free off-street parking. Entire house with pool (heating pool is no longer available). 3 mn walk to Shopping/restaurants. 15mn drive to Destin. 7 minute drive to beach. Decorated with original art from Madagascar, where the owner Yolande is from, and where Yolande's husband Clint worked for 24 years. Clint is a native of Ft Walton Beach and a Vietnam Combat Veteran. No pets allowed (even visitors' pets). NO CAMERAS HAVE BEEN INSTALLED ANYWHERE INSIDE THE HOUSE.

A spacious backyard features a heated pool surrounded by a stone deck. A shaded pergola offers seating, while blue Adirondack chairs are arranged near a fire pit. The area is well-lit with string lights, adding a welcoming touch to outdoor gatherings.

4.91 out of 5 average rating, 113 reviews

The Memory Maker - Heated Pool! 4BR Vacation Home

A cannonball into the pool and a family dinner outside. An evening by the fire roasting marshmallows and battling it out in a game of air hockey. Welcome to the Fort Walton Beach Memory Maker, where comfort meets fun and the best times are had. This four-bedroom amenity-packed home can sleep up to fourteen guests. Decorated with original hand-painted art (and ready for selfies), this property offers three queen beds, one king bed, and two full-size sleeper sofas.

Apartment in Okaloosa Island

A bright and airy living area features a light-colored sofa and matching armchairs arranged around a wooden coffee table. Coastal-themed artwork is displayed on the walls, and a flat-screen TV is mounted above a small console table. Natural light filters through sheer curtains.

4.83 out of 5 average rating, 111 reviews

Little Blue Gem

This charming condo is all about location, convenience, and fun. Just a 5-minute stroll to the beach, you’ll have your toes in the sand in no time.Step outside your back door, and the pool is right there waiting for you! Whether you’re lounging poolside or hitting the tennis courts, there’s always something to do. We’ve stocked this condo with everything you need—from pool toys to beach essentials, so just pack your swimsuit and get ready to relax and play!

4.98 out of 5 average rating, 166 reviews

A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.

Home in Pensacola Beach

Soundside Paradise

Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

A custom upright piano converted into a bar is displayed, featuring blue lighting and an array of glassware. A colorful art piece hangs above the piano, alongside a unique lamp atop a wine barrel. The modern decor enhances the inviting atmosphere.

5.0 out of 5 average rating, 132 reviews

1.5 mi to Beach-New Pool! Smart home-Modern Decor!

Joey’s place is a beautiful home in Navarre, Florida, less than 1.5 miles to the beach with a newly added pool (not heated) in June 2024! You'll have the home to yourselves (office & master closet locked). Close to restaurants and shopping, modern décor, smart home, garage parking. Pool added in June 2024. Extended Patio added in September 2024, 8 ft privacy fence added in December 2024. Mural painting on fence surrounding pool Fall 2026

Condo in Fort Walton Beach

4.96 out of 5 average rating, 114 reviews

Stars & Sea•Overlooking Pool & Sound•Sleeps 4

Kick back & relax in this calm, newly renovated ground-level condo on the Sound in Ft Walton Beach! ✨ Highlights: • 🌴 Waterfront views & stunning sunsets • 💦 Large resort-style pool • 🏖️ Minutes to beach access • 🍽️ Walk to local restaurants • 🚗 Easy parking & quiet community 🛏️ Queen bed w/Purple® mattress + Queen memory-foam sofa bed ☕ Kitchenette: Fridge • Air fryer/toaster • Microwave • Keurig •7.5 Miles to Destin

A spacious outdoor area features a large swimming pool, surrounded by a concrete deck. Lush greenery provides a natural backdrop, and a few lounge chairs are positioned nearby for relaxation.

4.91 out of 5 average rating, 151 reviews

Relaxing Pool Retreat Near Beaches & Destin!

Welcome to Our Happy Place! Whether you're planning a girls getaway, family beach vacation, couples retreat, or celebration weekend, Our Happy Place was designed to help you slow down, reconnect, and make lasting memories together. Perfect For: ✔ Girls Trips ✔ Family Vacations ✔ Couples Getaways ✔ Birthday Celebrations ✔ Parents Traveling with Teens ✔ Long Weekend Escapes ✔ Remote Work + Vacation Stays

Popular amenities for Mary Esther rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 140 reviews

Heated Pool-Fire Pit-Sun room -Near the Beach

4.96 out of 5 average rating, 149 reviews

The beach cottage features a welcoming exterior framed by palm trees and tropical foliage. A white picket fence surrounds the property, leading to a spacious porch with multiple steps. The home’s two levels and large windows create an open and airy appearance.

Home in Destin

Sugar Sand Cottage at Destin Pointe

4.91 out of 5 average rating, 133 reviews

Private Heated Pool, 10 Min to Navarre Beach

A heated pool is surrounded by a screened enclosure, offering a view of a spacious backyard with lush greenery. Two chairs are positioned nearby, inviting relaxation. The serene water reflects the natural light filtering through the enclosure.

4.91 out of 5 average rating, 103 reviews

Splash into serenity, pool, Sleeps 12

An inviting screened area features a heated saltwater pool surrounded by comfortable loungers and a dining set. A large umbrella provides shade for relaxation, while lush greenery offers a tranquil backdrop. Clear blue skies enhance the bright and airy environment.

4.96 out of 5 average rating, 107 reviews

Heated Salt Pool, 3 Kings, Near Beach.

A solar-powered swimming pool is enclosed within a netted structure, ensuring a bug-free environment. Colorful lounge chairs surround the pool, complemented by a shaded umbrella and a coffee table adorned with fresh flowers. Lush greenery is visible beyond the enclosure, enhancing the serene setting.

4.95 out of 5 average rating, 105 reviews

Covered Lanai | Heated Pool | Minutes to Beach!

4.6 out of 5 average rating, 10 reviews

Home in Mary Esther

Private Water Access | Heated Pool | Kayaks

A serene evening setting features a heated pool with a gentle curve, surrounded by a screened enclosure. A gas fire pit at the forefront glows, illuminating smooth stones and flames. Comfortable seating in the form of Adirondack chairs is positioned nearby, enhancing outdoor relaxation.

4.97 out of 5 average rating, 98 reviews

Heated Pool | Minutes to Navarre Beach | 2 Kings

Condo rentals with a pool

A sweeping view overlooking the beach showcases soft white sand and the Gulf of Mexico's gentle waves. Blue beach umbrellas are set up along the shore, with a designated swimming area visible. In the foreground, a swimming pool is bordered by palm trees and lounge chairs.

4.93 out of 5 average rating, 310 reviews

Okaloosa Island Top Floor 2BR Beach Condo

A spacious living area features a large sofa and a mounted television, along with soft blue lighting that creates a calming atmosphere. The decor includes a decorative wall unit and stylish accents, contributing to a welcoming environment for relaxation.

4.96 out of 5 average rating, 122 reviews

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach

A welcoming wooden sign is displayed at the entrance, painted in blue with white lettering that reads 'Welcome to the Beach House.' Decorative elements featuring seashells are included, emphasizing a vacation ambiance.

4.83 out of 5 average rating, 452 reviews

Condo across the street from the gulf

4.92 out of 5 average rating, 133 reviews

Beachfront Condo | Gulf Views | Okaloosa Island

4.93 out of 5 average rating, 130 reviews

Sublime Luxe Retreat + Free Beach Service

A serene beach scene captures the gentle waves lapping at the shore, reflecting the warm glow of the setting sun. The sky is painted in soft hues of orange and blue, creating a peaceful ambiance by the water.

4.87 out of 5 average rating, 195 reviews

2nd floor beachfront with amazing views

A spacious studio unit features a comfortable bed with light bedding and decorative striped accents. A seating area includes a grey sofa and a small table set, overlooking large glass doors that open to stunning ocean views. A neutral color palette enhances the coastal ambiance.

4.97 out of 5 average rating, 120 reviews

Gorgeous Gulf Front condo with amazing views!

A spacious and inviting living area showcases a large sectional sofa adorned with blue and white accents. Natural light fills the space through expansive sliding glass doors that offer a view of the Gulf. A ceiling fan provides a refreshing breeze while a coffee table and a patterned armchair complete the seating arrangement.

4.97 out of 5 average rating, 119 reviews

Condo With Serene Panoramic Views of the Gulf

Other holiday rentals with a pool

Apartment in Fort Walton Beach

4.88 out of 5 average rating, 125 reviews

B210 Pirates Plunder

4.89 out of 5 average rating, 38 reviews

Condo in Mary Esther

Peaceful Bay Retreat | Water Access, Pool & Dock

4.87 out of 5 average rating, 46 reviews

A well-appointed bedroom is presented, featuring a spacious bed with crisp white linens and a plush blue throw. Flanking the bed are two nightstands, each adorned with a lamp. Light-colored walls and closet doors create a serene setting.

Condo in Mary Esther

Emerald Coast Oasis

4.9 out of 5 average rating, 49 reviews

Two bright red kayaks are positioned on the sandy shore of a calm water body, partially surrounded by lush greenery. Beach towels and gear are sprawled across one kayak. The clear blue sky and distant trees enhance the serene waterfront setting.

Apartment in Mary Esther

Kayak Adventure. Dock, Pool, WiFi, Free Kayaks!

5.0 out of 5 average rating, 43 reviews

A community pool is set within a fenced area, featuring clear blue water and a gently sloping entry. Surrounding palm trees and shrubbery enhance the outdoor space. The pool area is bordered by a patterned brick patio, with lounge chairs positioned nearby for relaxation.

Townhouse in Mary Esther

Sound Beach Access w/ Water Views | 2BR/2.5 BA+W/D

4.87 out of 5 average rating, 30 reviews

A comfortable living space is observed, featuring a teal sofa and two light gray armchairs. Natural light fills the area through sliding glass doors that open to the waterfront patio. A decorative sign reading 'Relax' and a wall-mounted TV can be seen in the background.

Condo in Mary Esther

1st Floor 2br/1bth Dockside Condo near Hurlburt

4.65 out of 5 average rating, 198 reviews

A pool area is surrounded by trees, featuring a spacious deck with lounge chairs positioned around the clear water. The tranquil setting is complemented by a view of the bay, enhancing the outdoor experience.

Apartment in Mary Esther

Cozy Spot on the Bay with Island Views