Holiday rentals with a pool in Crestview

A bright living area features large sliding glass doors providing direct views of the beach. The space includes a dining table set for four and a cozy seating arrangement. Light colors throughout create a spacious and airy feel, complemented by coastal-themed decor.

4.97 out of 5 average rating, 107 reviews

Incredible View | Beachfront | Hot Tub

PLEASE read listing for info on property improvement project ★ DIRECT 5th Floor View of the Beach ★ Outdoor Pool ★ Free Parking ★ Outside Tiki Bar ★ On-Site Spa ★ Upgraded FAST Wi-Fi ★ Gym ★ Smart TVs & Cable ★ Gas Grills ★ Hot Tub ★ Beach Chairs ★ Beach Shop & Restaurant On Site ★ Steps to SunDestins private beach SunDestin Unit 506 Please read the entire listing before booking Thank you!

Home in Panama City Beach

The image captures a wooden staircase leading down to a sandy beach. The ocean is visible with gentle waves, reflecting a soft sunset glow. Beach chairs are arranged in the distance, and the sky features a blend of light blue and warm hues.

4.96 out of 5 average rating, 143 reviews

Heated Pool, Bikes! Steps to Beach, Alys, Rosemary

The largest house in the upscale gated Sunset Beach Community with private beach. This 3 Bedroom/3 Bath home is located on the south (beach) side of 30A and a short walk to restaurants and shops at Rosemary, Seacrest Beach, and Alys Beach. Reverse floor plan with living area on second floor and abundant natural sunlight. Just a 90-second walk to the beach access + heated, gulf-front pool overlooking the ocean, reserved exclusively for Sunset guests! Includes 4 bikes + new outdoor tv + daybed!

Apartment in Bluewater Bay

The exterior of the building is presented with a warm-toned sunset sky as a backdrop. The structure features a central door framed by tall glass panes, flanked by balconies. Lush landscaping with palm plants is visible in the foreground.

4.9 out of 5 average rating, 202 reviews

Upgraded Studio on the Water, come relax!

Experience Mother Nature's artwork from sunrise to sunset when you live on Choctawhatchee Bay at Bayside #309! This unit is cute, cozy, and upgraded it has everything you need for a weekend get away in the beautiful community of Bluewater Bay. You are 10-15 mins from Destin without all the traffic and hustle. If you stay within the community there are many amenities in Bluewater within 5 minutes. Relax, open a glass of wine and sit out on your baloney with amazing water views and landscapes.

Apartment in Navarre Beach

A cozy bedroom features a spacious bed covered in a light blue quilt. Two matching pillows are positioned at the head of the bed. A large window offers views of the surrounding landscape, with a picture of a coastal scene displayed above the bed.

4.95 out of 5 average rating, 168 reviews

La Playa Esmeralda - Panoramic Sunset Views

Welcome to La Playa Esmeralda, a beautifully renovated 2nd floor studio. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 2 comfortable beds-1 regular and 1 Murphy bed, along with a coffee bar and fully equipped kitchen. You're just a 5 minute walk to the beach. Enjoy a dip in the pool, grilling in the gazebo and fish all night long on our large, private fishing pier, no fishing license required. Early check-in avail.

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, 193 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.

Townhouse in Navarre Beach

A spacious deck overlooks the calm waters of the Sound, framed by a clear blue sky. Two round, textured outdoor poufs are positioned near the railing, inviting relaxation while enjoying scenic views of the shoreline and distant piers.

4.97 out of 5 average rating, 122 reviews

Waterfront, beach, dock - your Salty Air Retreat!

Embrace island living in our little corner of paradise! This beautiful, family friendly home offers you the ultimate getaway with the clear, calm waters of the Sound right outside your door and the emerald green waters of the Gulf across the street. Swim, fish, and paddle board from your own backyard. Or just enjoy the view from your hammock as your kids build sandcastles on the private white sandy beach. Discover for yourself why Navarre Beach has been named "Florida's Most Relaxing Place"!

Apartment in The Village of Baytowne Wharf

This ground floor studio features a spacious bed covered in striped linens. A flat-screen television is mounted on the wall opposite, with a small dining table nearby. A balcony with views of the golf course can be accessed through sliding glass doors, offering natural light.

4.94 out of 5 average rating, 139 reviews

Sandestin Elation Studio - Baytowne - Golf Cart

Ground-floor studio in Sandestin Golf & Beach Resort with serene golf course and lake views. Steps from Baytowne Wharf’s dining and entertainment. Features a king bed, queen sofa bed, full bath, and kitchenette with microwave and mid-size fridge. Enjoy Wi-Fi, Netflix, resort tram access, and beach gear in garage storage. Golf cart available - please inquire about availability and fee. Perfect for a relaxing escape in the heart of Sandestin. And Yes! you may drive the golf cart to the beach.

Home in Fort Walton Beach

A large, inviting pool is surrounded by a spacious deck with lounge chairs, creating a perfect area for relaxation. The fenced backyard features palm trees and green grass, providing a serene setting. The cottage’s exterior can be seen in the background, complementing the outdoor space.

4.99 out of 5 average rating, 104 reviews

Beautiful renovated cottage. Big backyard w/ Pool

Unwind in this fully renovated cedar cottage for an unforgettable stay. Located just 3.5 miles from the powder-sand beaches of Okaloosa Island. The property features a large backyard with a pool and plenty of room for grilling, lounging by the pool or for kids to play. The interior is cozy and modern with comfortable sleeping arrangements and a fully-equipped kitchen. With prime location, fantastic outdoor amenities and cozy interior, this is the perfect place to call home during your stay!

A large, mickey-shaped pool is surrounded by lounge chairs and tropical landscaping. In the background, the waterway can be seen, framed by palm trees and extending toward the horizon under a clear blue sky.

4.9 out of 5 average rating, 441 reviews

Relaxing Soundside Condo - WataView!

Vacation or work at our comfortable waterfront kitchenette studio in the heart of Fort Walton Beach. The sugar white sand beaches are just a short drive away, and adventure awaits right at your doorstep on Santa Rosa Sound. Includes pool and marina! Boat slip (28 Ft) available! The unit has a queen bed and futon that lays down to a full size bed. It's very comfortable for small groups. We are real owner-hosts and strive to keep our unit spotless and well supplied for our cherished guests.

A bright living area features a spacious gray sofa, complemented by a blue and white decorative pillow. Large glass doors open to a private balcony with ocean views. A dining table with white chairs and a chandelier is visible, alongside a wall-mounted flat screen TV and coastal artwork.

4.85 out of 5 average rating, 277 reviews

Majestic Ocean Views, Oceanfront Condo, Renovated!

Located right on the beach, this spacious condo has breathtaking unobstructed Gulf views, updated floors and appliances and sleeps six. Decorated in soothing designer colors with a coastal feel, the unit has a bedroom with a comfortable king size bed, flat screen TV and private bathroom; two bunk beds in a hallway alcove, a 2nd bathroom with shower, and open concept full size kitchen with all new full size stainless steel appliances, dining area and living room with a sleeper sofa..

4.95 out of 5 average rating, 135 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 NEWLY BUILT LUXURY COTTAGE DESIGN BEACH HOUSE WITH PRIVATE/HEATED POOL* AND GOLF CART in the heart of Santa Rosa Beach off 30A. This beach house is nestled among the trees yet only minutes away from the white sandy beaches. Bask in the sun by day and wind down and relax in the outdoor areas surrounded by a peaceful wooded area by night. It is like stepping out of one world directly into another. Come and Relax and enjoy the peace and tranquility of this cozy retreat.

4.97 out of 5 average rating, 178 reviews

The image captures the nighttime view of a screened-in pool area, illuminated by blue lights. The architectural structure showcases a modern design, with clear visibility of the surrounding landscape featuring trees and grassy grounds. Soft lighting enhances the atmosphere, suggesting a serene outdoor space.

Tiny home in Pensacola

Tiny Home Pool View 25 Mins to Beachb

Welcome to our cozy tiny home located in my secured backyard, where a queen-sized bed promises a peaceful night’s sleep and our well-equipped kitchenette simplifies meal preparation. You will have free parking located in the backyard just steps away from the tiny home. Additionally, you’ll have the opportunity to gather around the outdoor fire pit for cozy evenings under the stars. Inside, unwind with a smart TV and stay connected with complimentary Wi-Fi.

Popular amenities for Crestview rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 140 reviews

A bright living area features a neutral sofa adorned with decorative pillows and a light textured throw. Two wicker chairs, a glass coffee table, and an artisan wood accent piece enhance the space. Natural light is welcomed through multiple windows, surrounded by plantation shutters.

Home in Inlet Beach

30A Beach Villa-Steps to PrivateBeach! Dogs,Bikes

4.92 out of 5 average rating, 108 reviews

A wooden walkway leads down toward the sunlit beach, where soft white sand contrasts with the vibrant blue water. Beach umbrellas and chairs are set up along the shore, with gentle waves lapping at the edge. Clear skies further enhance the coastal scene.

Home in Santa Rosa Beach

StayOn30A Renovated Beach Home-Across from Beach!

4.94 out of 5 average rating, 212 reviews

A modern retreat is showcased with a striking dark exterior and large glass windows. The wooden deck is complemented by outdoor seating, while lush greenery surrounds the home, creating a serene setting within the pine forest.

Home in Pace

The Pine House Pace, FL

4.96 out of 5 average rating, 199 reviews

A private heated pool is surrounded by a spacious concrete deck and lounge chairs. Tall palm trees provide shade, and an outdoor dining set sits under a large umbrella. The inviting home is partly visible in the background, bathed in warm sunlight.

Home in Destin

Walk to Beach · Private Heated Pool · Fenced Yard

4.99 out of 5 average rating, 102 reviews

Home in Sandestin

6-Seater Golf Cart with Bay, Lake & Golf View Home

Home in Fort Walton Beach

A serene outdoor space features a private pool enclosed by a safety fence. Colorful seating options are arranged on a decorative mosaic patio, complemented by an umbrella providing shade. Lush trees provide greenery in the background, enhancing the peaceful atmosphere.

4.92 out of 5 average rating, 191 reviews

#2 4BR HUGE PET Friendly Home Away from Snow!

4.99 out of 5 average rating, 100 reviews

Home in Santa Rosa Beach

New Interior | New Golf Cart | Pool | Beach

5 out of 5 average rating, 124 reviews

Home in Pensacola

Quiet & Cozy Family Home! Perfect Winter Stay!

Apartment rentals with a pool

A comfortable living area features a cozy gray couch with decorative pillows, complemented by a blue accent chair. A wooden coffee table sits on a light rug, and wall art depicting nature is displayed above. A dining table for four is positioned nearby.

4.97 out of 5 average rating, 376 reviews

Dog Friendly, 1 Bdr 1 Bath, Private Beach & Pool

A modern living area features a sleek fireplace and a large wall-mounted flat-screen TV. A comfortable dark sofa and a patterned armchair provide seating. Large sliding glass doors open to a balcony with ocean views, allowing natural light to brighten the space.

4.99 out of 5 average rating, 134 reviews

High-End Beachfront Condo w/Breathtaking Gulf View

Palm trees frame the view, which showcases a waterfront area with a private dock extending into the intercoastal waterway. Nearby, boats are moored at multiple docks, with buildings visible in the background. A grassy area leads to the water's edge.

4.97 out of 5 average rating, 325 reviews

Just For You In Fort Walton Beach

Two wicker chairs are positioned to face expansive windows displaying panoramic views of the Gulf. A glass table is situated between the chairs, enhancing the inviting and relaxed atmosphere. Natural light floods the space, creating a bright and airy environment.

4.95 out of 5 average rating, 105 reviews

Beachfront Panoramic Views Balcony Heated Pool

Apartment in Santa Rosa Beach

The living area features a spacious layout with a comfortable sofa and two armchairs positioned around a wooden coffee table. A dining area with four chairs is visible near a fully-equipped kitchen. Light fills the room through large windows, highlighting the king bed in the background.

4.98 out of 5 average rating, 135 reviews

Prime 30A Location/Pool/200 feet to beach/Wi-Fi

Apartment in Miramar Beach

A balcony features a round table with four high-backed chairs, all set against a backdrop of ocean views. The vibrant blue sky meets the water in the distance, while palm trees and buildings are visible below.

4.91 out of 5 average rating, 159 reviews

Miramar Beach Ocean View with Large Balcony

The living area features a light-colored sofa paired with a matching armchair, arranged around a white coffee table. A large television is positioned on a console, and floor-to-ceiling windows provide views of turquoise waters and the balcony. Soft curtains frame the windows.

4.85 out of 5 average rating, 237 reviews

Breathtaking views! 2024 updated condo in Destin

The living area features a light-colored sofa and a wooden coffee table, with a flat-screen TV on an entertainment unit. Natural light enters through sliding glass doors leading to a balcony with outdoor dining furniture, providing views of the bay.

4.91 out of 5 average rating, 106 reviews

Destin West, Bayside, 2 BR+ Bunk Room, sleeps 8

Other holiday rentals with a pool

4.97 out of 5 average rating, 77 reviews

The exterior of the unit features a welcoming front entrance with a white door and decorative signage. A well-maintained path of stones leads to the door, surrounded by colorful plants and mulch. A white wooden fence provides privacy, while natural greenery can be seen in the background.

Flat in Milton

Newly Remodeled 1 BR/1BA with Private Entrance

5 out of 5 average rating, 14 reviews

Flat in Destin

Make memories at 274

5 out of 5 average rating, 26 reviews

The exterior of the home showcases a single-story structure with a covered entryway and a two-car garage. Two chairs are positioned on the front porch. The surrounding yard features a neatly mowed lawn and is enclosed by a wooden fence in the background.

Home in Baker

The Mill House: Newly Installed Above Ground Pool!

Superhost

A large, inviting pool area is showcased, with crystal clear water reflecting the blue sky. Surrounding tropical landscaping and a community building with a peaked roof is visible in the background, enhancing the outdoor leisure environment.

Townhouse in Crestview

4.77 out of 5 average rating, 39 reviews

Cozy Poolside Escape

Superhost

Farm stay in Baker

5 out of 5 average rating, 3 reviews

Meant to Bee Farm

Superhost

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.

Flat in Fort Walton Beach

4.78 out of 5 average rating, 87 reviews

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

A balcony table with four wooden chairs is positioned overlooking the Gulf. The horizon merges the tranquil blue sea and sky, reflecting sunlight. The unobstructed view enhances the outdoor space, inviting relaxation while watching the waves below.

4.98 out of 5 average rating, 46 reviews

Pelican Beach 19th Floor 1 Br - on the Beach

A bright kitchen features modern stainless steel appliances and quartz countertops, with soft-close cabinets providing ample storage. The cozy living area includes a comfortable sofa and colorful decor, while the serene beachfront is visible through the window, where gentle ocean waves meet a colorful sky.