Vacation rentals with a pool in Mary Esther

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.

A private heated pool is framed by a spacious patio area, featuring a floating swan inflatable. Surrounding the pool are lounge chairs and a shaded area enhanced by string lights, creating an inviting outdoor space. The fenced yard offers a backdrop of trees and open sky.

4.94 out of 5 average rating, 199 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

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.

Apartment in Fort Walton Beach

A spacious bedroom features a comfortable bed with blue and white striped bedding, complemented by a large round pillow. Two accent chairs are placed nearby, and large windows allow natural light to fill the room. A modern bathroom is accessible through a door.

4.82 out of 5 average rating, 106 reviews

Luxury Pool/SPA/BEACH, 1BR w/Dol Views, Full KITCN

The Crow’s Nest is part of the Manor on the Bay, a large home transformed into multiple rental units. The full property is also avail for rent. This pvte 2nd story space bosts nautical design elements. Sip coffee on your balcony while watching the dolphins play. With options to cook in the well appointed galley kitchen or check out our local sea food spots, you wont leave here hungry. What I love: ✔ stunning views ✔ pvte space ✔ HUGE luxury spa w/pool & beach ✔ Dolphins! ✔ Book what you need

4.96 out of 5 average rating, 101 reviews

An aerial view captures a beachside community with a blend of buildings and green spaces. The soft, white sand stretches along the shoreline, dotted with colorful umbrellas and beach chairs, providing a visual representation of the beach access available for guests.

Villa in Destin

Sandpiper Cove 8140! 500 ft to the Beach!

Free beach setup which includes 1 reserved umbrella and 2 chairs between March 1st and October 31st! 1,100 feet of private beach access owned by Sandpiper Cove! 4 beach towels are provided with unit 8140! 1 of the 5 pools is in the back terrace; steps away from the back porch of the villa! 1 restaurant, 1 beach side bar, a pitch and putt golf course, tennis and pickleball courts all on site. Minutes from several local attractions! About 17 miles from the Destin-Fort Walton Beach Airport!

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

This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.

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, 338 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 balcony view showcases bright blue outdoor chairs and a small table. Below, a spacious pool is surrounded by lush greenery and palm trees, with marina access visible in the background. The serene waters of Santa Rosa Sound reflect the cloudy sky.

4.98 out of 5 average rating, 99 reviews

Soundside Waterfront Condo

Our sunny waterfront condo on the Santa Rosa Sound makes a great home base for your Okaloosa Island, Destin, Hulburt & Fort Walton Beach experience! Minutes from downtown FWB dining & shopping, boat rentals to Crab Island and Gulf of Mexico, and the numerous Okaloosa Island beaches and Boardwalk. There are two large pools, outdoor BBQ area, and over a 1/4 mile of docks for fishing, boating, or just walking to see the spectacular views and sunsets of the waterway.

4.98 out of 5 average rating, 164 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

4.97 out of 5 average rating, 111 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

4.97 out of 5 average rating, 138 reviews

The backyard area features a private pool surrounded by lounge chairs and a paver patio. Palm trees add a tropical touch beside the home, which is illuminated against a twilight sky. A barbecue grill is visible, along with a seating area for outdoor relaxation.

Home in Destin

Pool, Golf Cart, Fire Pit, & Walk to Beach

4.96 out of 5 average rating, 160 reviews

The newly built cottage features a two-story design with light-colored siding, surrounded by lush greenery. A golf cart is parked nearby on a gravel path, adding convenience for exploring the area. Sunlight filters through the trees, creating a serene atmosphere.

Home in Santa Rosa Beach

Luxury 30A Cottage w/ Private Pool and Golf Cart

A spacious screened-in lanai is showcased, featuring a gathering area with a circular seating arrangement. A gas fireplace adds warmth, while soft lighting illuminates the saltwater pool outside, creating a calming ambiance. Colorful lounge chairs line the pool for relaxation.

4.99 out of 5 average rating, 104 reviews

Salt Pool & Spa, Heat Opt, Cali King Bed, Beach 4M

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, 103 reviews

Covered Lanai | Private Pool | Minutes to Beach!

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.

4.97 out of 5 average rating, 104 reviews

Heated Salt Pool, 3 Kings, Near Beach.

4.89 out of 5 average rating, 124 reviews

NEW ~Sundancer~*Huge Pool *Hot Tub *Game Room*

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

4.6 out of 5 average rating, 10 reviews

Home in Mary Esther

Private Water Access | Heated Pool | Kayaks

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, 309 reviews

Okaloosa Island Top Floor 2BR Beach Condo

The image displays a direct view from the private balcony overlooking the sandy beach and the Gulf of Mexico. The soft white sand stretches into the distance, meeting the calm waters with varying shades of blue and green under a clear sky.

4.89 out of 5 average rating, 213 reviews

Relaxing Gulf Front Couple's Retreat*Beach Service

4.88 out of 5 average rating, 598 reviews

Cozy Soundside Condo - WataView!

4.92 out of 5 average rating, 133 reviews

Beachfront Condo | Gulf Views | Okaloosa Island

A well-appointed studio condo features a spacious bed adorned with a coastal-themed blanket. Nearby, a love seat and a dining area with contemporary lighting elements are visible. Light, neutral wall colors create a calm atmosphere, complemented by tasteful decor, including ocean-themed accents.

4.84 out of 5 average rating, 308 reviews

B103 Coastal Connection at Pirates Bay

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, 284 reviews

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

4.96 out of 5 average rating, 584 reviews

An open living area features a modern chandelier above a glass dining table, with comfortable seating arranged around a large window. The expansive view showcases the ocean and balcony, complemented by soft beige and turquoise decor.

Condo in Destin

Ocean Paradise - Beach view - Bonus Beach Service

4.88 out of 5 average rating, 356 reviews

A modern kitchen is seen alongside a dining area with a table and stools. The open living space features a sofa and accent chair, with natural light filtering in from a large window. A cozy sleeping area is positioned in the background, adorned with soft decor.

Condo in Pensacola Beach

The Sandy Secret

Other vacation rentals with a pool

Vacation home in Fort Walton Beach

A serene outdoor space features a heated pool reflecting the evening sky in shades of pink and purple. Cozy white lounge chairs are positioned nearby, and a patio area with ambient lighting is visible, enhancing the atmosphere. A hot tub and fire pit are also present.

4.91 out of 5 average rating, 184 reviews

Coastal Escape: Heated Pool, Hot Tub, Grill!

4.89 out of 5 average rating, 38 reviews

Condo in Mary Esther

Peaceful Bay Retreat | Water Access, Pool & Dock

4.96 out of 5 average rating, 72 reviews

Townhouse in Mary Esther

Waterfront Sound Tri-level TH

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

4.65 out of 5 average rating, 196 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

4.89 out of 5 average rating, 47 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!

4.87 out of 5 average rating, 30 reviews

Condo in Mary Esther

Comfy 2BR Dockside Retreat