Holiday rentals with a pool in Crestview

Two beach chairs are set up beneath a colorful umbrella on a sandy shore, with soothing waves visible in the background. Towels are draped over the chairs, and a cooler is placed on the sand, creating a welcoming spot for relaxation by the water.

4.91 out of 5 average rating, 178 reviews

Sunrise Destination-Hot Tub&Heated Pool-Beach View

“Sunrise Destin-ation” is the perfect spot for your next Destin getaway! “5-10 minutes away from everything - from the Beach, across the street, to limitless restaurants. Prime location for a trip to Destin!” – Cordelra, ‘23.. Our cozy condo, with a king bedroom, a twin-bunk alcove, and a queen sleeper sofa accommodates up to 6 guests easily. Come indulge in our community pool (seasonally heated), hot tub, and enjoy being STEPS from 2 gorgeous public beach access points directly across the str

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, 169 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.

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

Beachfront Corner Condo in Destin - Panoramic Gulf Views Summer dates just released! Experience luxury in our Destin beachfront condo! This 3-bedroom, 2-bath unit offers panoramic Gulf views from the living area, kitchen, and master bedroom. Enjoy a renovated balcony, heated pool, tennis, basketball, pickleball, gym, and sauna. Beach chairs and umbrella included March-October. Convenient elevator and steps access. Book your Destin vacation rental now for an unforgettable beach getaway!

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, 328 reviews

Just For You In Fort Walton Beach

Free parking. elevator access, Aquamarine w/white décor. tile floors. studio with 1 queen bed, 2 smart TVs, intercoastal waterway view, off-street parking, 24-hour security, swimming pool, picnic/bbq area, cable TV, wifi, full bath, fully-equipped kitchen, microwave, convection oven. Balcony for viewing waterfront. Viewing area for sunset. No pets allowed. No service animals allowed due to guests' allergies which can cause physical reactions. NO CAMERAS ANYWHERE INSIDE THE CONDO.

Apartment in The Village of Baytowne Wharf

The pool area features a large, inviting swimming pool surrounded by palm trees and lounge chairs. The clear blue water reflects the sky, creating a serene atmosphere. The pool deck is accented by gentle landscaping, providing a lush, tropical feel.

4.95 out of 5 average rating, 124 reviews

Peaceful Waters in Baytowne Wharf with Pool

Create lifelong memories in the charming neighborhood of Baytowne Wharf located in the most desirable resort the Emerald Coast has to offer - Sandestin Golf and Beach Resort. From dipping in the sparkling waters of our swimming pools to digging in the sugar-like sand of the beach, your family and guests have access to wonderful amenities. This 1 bed/1bath condo with pull-out sleeper is perfectly situated to ensure everyone has an unforgettable experience. We look forward to hosting you.

Apartment in The Village of Baytowne Wharf

A spacious studio features a king bed dressed in blue and white striped linens. Soft lighting from bedside lamps creates a relaxed atmosphere. A sitting area with a chair sits beside a window, which allows natural light to filter through sheer curtains, offering views of the outdoors.

4.94 out of 5 average rating, 149 reviews

Sandestin Bahia 2nd floor - Baytowne Wharf Studio

Chic studio with bay views in Sandestin Golf & Beach Resort, steps from the Village of Baytowne Wharf. Perfect for a romantic getaway with sunset views, resort tram access, and walkable dining and nightlife. Features a king bed, queen sofa, stylish décor, and kitchenette with mid-size fridge, microwave, blender, and toaster. Enjoy Wi-Fi, Netflix, and beach gear stored in our private garage-level storage. Perfect for couples or small families looking to relax and explore Sandestin.

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.

4.98 out of 5 average rating, 193 reviews

A spacious outdoor area is enclosed with a framed structure, featuring soft blue and white lighting along the floor. Potted plants add a touch of greenery, while lounge chairs are neatly arranged within the space, providing a relaxing ambiance for outdoor gatherings.

Tiny home in Pensacola

Tiny Home Pool View 25 Mins to Beacha

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 in the backyard located 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.

4.99 out of 5 average rating, 153 reviews

Four Segway electric scooters are lined up on a patterned stone driveway. Each scooter features a sleek design with distinct colors, and sturdy wheels suited for various terrains. The garage door is visible in the background, highlighting the residential setting.

Townhouse in Watersound

Big Chill 30A | Scooters | Pool | Nearby Beaches!

Experience 30A luxury in this newly built, professionally designed townhome in Prominence. Just 5 min by bike or scooter to Gulf Lakes or Deer Lake beach access (PUBLIC). Located near Alys, Rosemary, pristine beaches, and top-rated local restaurants. - Fully-equipped Kitchen - 4 Segway Electric Scooters - 4 Beach Cruisers & Small Child Bike Trailer (Fits 2) - Beach Towels, Umbrella, Chairs, Sand Toys - Heated pool - Across from The BIG CHILL

A bright and airy living space features a comfortable sofa adorned with decorative pillows. A coffee table sits in front, complemented by a cozy throw. Large glass doors reveal a balcony with views of the pool, framed by palm trees and natural light.

4.76 out of 5 average rating, 191 reviews

Serene Waterfront Studio Fort Walton Beach Condo

Step inside and you'll find a bright and airy living space with a plush queen-size bed, comfortable seating area, and a flat-screen TV with cable. The kitchenette is equipped with everything you need to whip up a quick meal, including a mini fridge, microwave, and coffee maker. With the beach just a drive away, you'll have plenty of opportunities to soak up the Florida sun and enjoy the Gulf Coast's famous white-sand beaches.

Popular amenities for Crestview 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, 148 reviews

A two-story beach house displays a welcoming front porch, framed by palm trees and lush landscaping. A stone pathway leads to the entrance, and bicycles are positioned nearby, adding to the beach ambiance. The structure features light-colored siding and a variety of large windows.

Home in Santa Rosa Beach

Divine Beach Living at 'On Beach Time'

4.96 out of 5 average rating, 127 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

4.94 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

5 out of 5 average rating, 107 reviews

The exterior of a two-story coastal home is presented, featuring a white façade with ample blue accents. A covered porch extends along the front, showcasing large windows and doors. Lush green landscaping and a picket fence enhance the inviting entrance, complemented by an American flag gently waving.

Home in Destin

Private Pool - Golf Cart - Block to Beach - Destin

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, 193 reviews

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

4.96 out of 5 average rating, 120 reviews

A charming beach house exterior is showcased, with a well-maintained pool area surrounded by lounge chairs and a patio. A set of steps leads to a spacious deck area, featuring a seating arrangement with colorful cushions and nearby bicycles. Lush greenery surrounds the property.

Home in Santa Rosa Beach

30A 5 Min Walk to Beach/View/Private Pool/Family

Home in Fort Walton Beach

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.

4.89 out of 5 average rating, 132 reviews

Emerald Coast Retreat Near Destin

4.95 out of 5 average rating, 218 reviews

An outdoor area features a private saltwater pool illuminated in blue. Surrounding the pool are wooden lounge chairs and a covered seating area with soft lighting. The backdrop includes lush trees and a well-equipped outdoor kitchen, making it an inviting space for relaxation.

Home in Seacrest

Pet Friendly 30A Heated Pool Ocean View Beach 0.10

Apartment rentals with a pool

4.99 out of 5 average rating, 204 reviews

100 ft to sand, Corner unit, Hot Tub, Garden view

A table set for refreshments showcases a spread of crackers, cheese, fruits, and chilled water with lemon. In the background, the emerald waters of the Gulf are visible, with beach umbrellas dotting the shoreline under a partly cloudy sky.

4.99 out of 5 average rating, 107 reviews

Spacious, elegant, beachfront, w/office

Apartment in The Village of Baytowne Wharf

The expansive pool area features a zero-entry design, surrounded by lush palm trees and tropical landscaping. Sun loungers are arranged along the poolside, and the elegant Grand Complex building provides a scenic backdrop, all under a clear blue sky.

4.96 out of 5 average rating, 103 reviews

"Sweet & Salty" @ Sandestin’s® Baytowne Wharf

A large, inviting swimming pool features colorful floating lily pads and a rope bridge. Surrounding the pool are palm trees and lounge chairs, with poolside umbrellas providing shade. A colorful bar area is visible in the background, enhancing the resort's family-friendly atmosphere.

4.86 out of 5 average rating, 201 reviews

Waterpark Condo with Free Beach Setup & Aqua Pass

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, 139 reviews

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

The living area features a light-colored sofa adorned with colorful cushions, complemented by a patterned area rug. A ceiling fan is visible above, and large glass doors open to a balcony with a view of the beach. A wall art piece depicting a whale adds character to the space.

4.94 out of 5 average rating, 138 reviews

Beach front 2/2 with gulf view.

Apartment in Santa Rosa Beach

A spacious studio features a King size bed with a white quilt, positioned near a cozy seating area that includes a white sofa and striped accent chair. A modern kitchen island with a wooden countertop and stainless steel appliances is visible. Natural light enters through large mirrors and windows, highlighting rustic wooden beams overhead.

4.89 out of 5 average rating, 114 reviews

Beach Retreat 30A Seagrove

Apartment in Santa Rosa Beach

A wooden staircase leads down to the expansive sandy beach. The calm turquoise water stretches into the distance, with several blue umbrellas arranged on the shore, providing shade. The clear sky enhances the serene beach atmosphere.

4.92 out of 5 average rating, 210 reviews

1/ Br/ 1 Ba condo @ Gulf Place! ~Private beach ac

Other holiday rentals with a pool

4.97 out of 5 average rating, 78 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

Apartment in Bluewater Bay

A serene waterfront view is presented, showcasing calm waters under a clear blue sky. Lush green grass and well-kept shrubs frame the scene, leading to a wooden dock extending into the bayou, offering an inviting spot to relax and enjoy the surroundings.

4.84 out of 5 average rating, 50 reviews

* The Dock Condo * Waterfront zen in Bluewater

5 out of 5 average rating, 27 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

Farm stay in Baker

5 out of 5 average rating, 3 reviews

Meant to Bee Farm

Flat in Fort Walton Beach

5 out of 5 average rating, 26 reviews

Top Floor Waterfront View Studio

A spacious living area is presented with a large reclining leather couch and a glass coffee table atop a neutral area rug. A wall-mounted television and a decorative round mirror adorn the walls, while light filters in through the sliding glass door leading to an outside space.

5 out of 5 average rating, 18 reviews

The Funky Monk

Flat in Fort Walton Beach

A boardwalk leads to a sandy beach, lined with umbrellas and beach chairs under a clear blue sky. Soft waves can be seen gently lapping at the shore, while people enjoy their day on the beach in the distance.

4.95 out of 5 average rating, 55 reviews

Gulf View Island Studio w/ Restaurant Nearby