Holiday rentals with a pool in Crestview

5 out of 5 average rating, 114 reviews

Waterfront cozy condo with king bed & resort pool

Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

The image depicts a vibrant pool area surrounded by lush palm trees, extending toward the Gulf of Mexico in the background. Families are enjoying the water, with splash pads and colorful play structures visible. Sun loungers and umbrellas are placed around the pool deck.

4.92 out of 5 average rating, 183 reviews

Waterscape 4th Flr 1 Bedroom w Bunks on the beach

Relax in this beautifully decorated 1BR/2BA condo at Waterscape Resort with 4th-floor views of the courtyard, heated pool, and partial beach/ocean views. The master bedroom features a king bed and en-suite bath. Kids love the bunk beds with TVs. The unit also includes a sofa bed, stainless steel appliances, new flooring, in-unit washer/dryer, and beach chairs with an umbrella. Many repeat guests return for the bunk beds and resort amenities, including three pools, a waterfall, and a lazy river.

4.94 out of 5 average rating, 210 reviews

Home in Pace

The Pine House Pace, FL

Enjoy this UNIQUE retreat! Located on 3 acres of lush pines, this home is the perfect getaway for you or your family. With the romantic modern vibe of the house, you are sure to feel RELAXED, REJUVENATED and ready for whatever is next. Cool the day off in our backyard SITTING POOL, or read a book in our 7 ft SITTING WINDOW. Watch the pines sway through our living room observing windows or have friends over for dinner at our outdoor dining area! No matter the reason, the Pine House is for you!

4.98 out of 5 average rating, 123 reviews

A spacious living area features a large sectional couch and a coffee table, with high ceilings accentuated by ceiling fans. Natural light floods in through multiple large windows, illuminating the adjoining kitchen and dining space, where a modern dining table awaits.

Home in Santa Rosa Beach

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

This is your 30A Florida escape, where relaxation meets adventure and every amenity imaginable. Guests rave about our extras! This pet friendly home has a fenced-in backyard, private pool (heated upon request), smart TVs with streaming apps, games room, sports gear (rackets, bicycles, and more)—perfect for families. Minutes from Sandestin Miramar Beach, Santa Rosa Golf Club, you're close to the area's top beaches, dining, world-class golf courses, and scenic trails. All that’s missing is you.

Townhouse in Santa Rosa Beach

A bright living area is showcased with natural wood flooring and warm lighting. Comfortable seating is arranged around a spacious coffee table, complemented by a textured area rug. A dining area with light chairs is visible in the background, enhanced by a decorative light fixture.

4.97 out of 5 average rating, 103 reviews

Luxury Townhouse in Santa Rosa Beach - The Zen Pad

Top Reasons to Book this 30A Luxury Townhome: * Few minute walk to the beach access point: Directly across 30A * Beautifully renovated in 2024 * Spacious and Peaceful * 3 Balconies * 2 Pools, Tennis / Pickle Ball Courts, Fishing Ponds, BBQ area, etc. * 25+ miles of hiking trails just steps away * Perfectly located near the beach, trails, shopping, grocery, dining, & more! * Great for families or individuals * Fast Wifi for remote work or streaming * Voted as Guest Favorite AIRBNB!

Apartment in The Village of Baytowne Wharf

A spacious studio features a king bed adorned with neutral linens and an array of decorative pillows. Natural light flows through sliding glass doors that lead to a private balcony, while a comfortable queen sofa is positioned nearby, offering additional seating.

4.9 out of 5 average rating, 262 reviews

Stylish Coastal Baytowne Studio Amazing Amenities

Enjoy a stylish experience at this centrally-located studio on the Sandestin Resort right in the heart of the action of Baytowne Wharf Village. Newly renovated Welcome to paradise! Unit is located on the 5th floor of Pilot House allowing quick walking access to entertainment, food and pool. Only 10 minutes from the beach without ever leaving the Resort, Including Free Tram! The unit offers a King bed with luxury linens. Comfortable queen sofa that will fit two more guests or children.

The landscaped grounds feature a grassy area bordered by palm trees, leading to a mickey-shaped pool. The backdrop includes a waterfront view with boats visible, along with the multistory building where the studio units are located.

4.88 out of 5 average rating, 572 reviews

Cozy Soundside Condo - WataView2!

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.

Apartment in The Village of Baytowne Wharf

A spacious studio layout is illustrated, featuring a king size bed with blue bedding and a cozy sofa in a warm blue tone. Bright natural light filters in through large windows, with a dining area set near the kitchenette and a decorative rug adding color to the space.

4.94 out of 5 average rating, 160 reviews

Serene Condo w/ Shared Pool, Hot Tub & Bch Access

Sleeping up to 4 guests, this premium studio provides you with everything you will need for a perfect beach vacation while indulging in the luxurious resort life. Sandestin Golf and Beach Resort features over 7 miles of beaches, a pristine bay front, 4 championship golf courses, 15 world-class tennis courts, a 226-slip marina, a fitness center, a spa, and celebrity chef dining. Enjoy the fun and entertainment at The Village of Baytowne Wharf with shops, restaurants, playgrounds & more!

5 out of 5 average rating, 119 reviews

A golf cart is parked on a paved path, featuring comfortable seating for up to four passengers. The background is filled with palm trees and a pergola, with a sunset sky displaying shades of orange and purple.

Townhouse in Watersound

Prominence 30A: NEW Golf Cart, Bikes, Pool

Southern Bliss has the sophistication of a modern beach house with a coastal vibe. This 3B/2.5B home is a short walk to the resort style pool and The Big Chill (aka The Hub) to enjoy restaurants, shops, shows, movie nights and concerts. Minutes to the beach using the golf cart or bikes provided is an added bonus! This stunning home will guarantee your vacation needs are met. Enjoy the fully equipped kitchen, new furniture/decor, comfortable beds, beach gear, and washer/dryer!

4.97 out of 5 average rating, 180 reviews

A charming beach house with a light-colored facade is framed by greenery. A paved driveway leads to the entrance, flanked by two beach cruiser bikes and a small outdoor seating area with a table. Sunlight filters through the trees, enhancing the inviting appearance.

Home in Santa Rosa Beach

Small Waves-30A beachhouse w golf cart/neighb pool

Small in stature but grand in design, this 30A beach house will wow you. Access to neighborhood pool, gym, & the beautiful white sand beaches a few blocks away. Small Waves is set in the Blue Mountain Beach area, which is well-known for its charm, its restaurants, & its famous ice cream shop. We have an EV car charger for electric cars (no extra fee) plus access to an electric golf cart (extra fee). Bedroom has a king size bed & twin bed & there are also 2 twin beds upstairs.

4.95 out of 5 average rating, 134 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.

5 out of 5 average rating, 121 reviews

Home in Pensacola

Cozy Winter Relaxing! Pensacola Poolside Retreat!

Discover this inviting 3BR, 2BA family-friendly retreat in beautiful Pensacola, designed for up to 6 guests. Relax in your own private pool oasis, enjoy the spacious interior, and cook with ease in the fully equipped kitchen. Located only minutes from Pensacola Beach, local attractions, and Navy bases, it’s the perfect spot to unwind and explore. Join the 100+ guests who left 5-star reviews—they love the peaceful vibe and unbeatable convenience!

Popular amenities for Crestview rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 109 reviews

A screened-in pool area features a clear, blue pool surrounded by a spacious deck. Lounge chairs are positioned around the pool for relaxation. Lush palm trees and greenery are visible in the background, offering a glimpse of the outdoor environment.

Home in Pensacola Beach

Fun, sun, sand, and rest. Enjoy your stay with us.

Home in Fort Walton Beach

An outdoor view of the home showcases a private pool surrounded by lounge chairs and a covered patio. Soft lights illuminate the area, highlighting the inviting atmosphere as dusk settles, with a colorful sky reflecting off the water.

4.94 out of 5 average rating, 36 reviews

* NEW * 3BR Pool & Hot Tub l 10 min to Beach

5 out of 5 average rating, 25 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!

4.96 out of 5 average rating, 25 reviews

A heated pool with a gentle curve is framed by a spacious patio and an expansive gazebo. Several bar stools line the outdoor seating area, providing a space for relaxation. Lush grass surrounds the area, complemented by a sun umbrella and palm trees under a clear blue sky.

Home in Navarre

Heated Pool, Gazebo & Fire Pit. 3 Miles to Beach!

4.99 out of 5 average rating, 100 reviews

Home in Sandestin

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

4.92 out of 5 average rating, 24 reviews

A comfortable living area features a light gray sofa and matching loveseat, both adorned with soft pillows. A wooden coffee table rests on a textured area rug, with natural light filtering through a sheer curtain by a window. A potted plant adds a touch of greenery.

Home in Navarre

Bungalow (w/ pool and access to bayfront property)

4.94 out of 5 average rating, 17 reviews

An open-concept living area features a dining table with matching benches and a kitchen island with bar seating. Modern light fixtures hang above, and a television is mounted on the wall. Light wood flooring complements the contemporary aesthetic, creating a welcoming space.

Home in DeFuniak Springs

North End Retreat | 3 Bed 2 Bath

5 out of 5 average rating, 12 reviews

A shaded patio area features a picnic table and several lounge chairs arranged around a blue in-ground pool. A privacy fence surrounds the yard, while a pink umbrella is seen towards the back. A wooden deck is visible in the background.

Home in Crestview

PrivatePool/Oasis/WholeHouse/nearBeachesDestinFWB

Apartment rentals with a pool

A private balcony is featured, showcasing a round table with two chairs. The expansive view includes the Gulf waters and sandy beach under a partly cloudy sky with sunlight reflecting off the water.

4.94 out of 5 average rating, 177 reviews

Gulf View Studio condo Fort Walton Beach

Apartment in Pensacola Beach

A private balcony offers sweeping views of the Gulf of Mexico, showcasing the clear blue waters and soft sandy beach below. The horizon merges sky and sea, creating a serene coastal scene. Beach chairs and umbrellas are positioned along the shoreline, inviting relaxation.

4.98 out of 5 average rating, 211 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

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, 126 reviews

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

4.88 out of 5 average rating, 102 reviews

A serene bedroom features large floor-to-ceiling windows showcasing stunning Gulf views. A spacious bed is dressed in soft linens, and a TV is positioned on a wooden dresser. Natural light fills the room, complemented by light curtains and coastal decor.

Apartment in Sandestin

CostaVista-Sandestin®: Steps to Beach/Gulf Views!

A comfortable living area is presented with a light-colored sofa adorned with soft blue cushions. A wooden coffee table is centered in the space, featuring a decorative bowl and coaster items. Two floor lamps illuminate the room, enhancing the wall art depicting serene trees.

4.98 out of 5 average rating, 171 reviews

*Snorkeling Cove* beach-1st floor-*King bed/Suite

Apartment in Santa Rosa Beach

A modern living area features a large flat-screen TV displaying a sunset graphic. Cozy seating is provided by two light-colored armchairs and a dark sofa. The space includes an open kitchen with white cabinetry and stainless-steel appliances, along with a textured area rug beneath a coffee table.

4.98 out of 5 average rating, 181 reviews

Great Stay on 30A - Studio in Seagrove

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.

4.92 out of 5 average rating, 281 reviews

Okaloosa Island Top Floor 2BR Beach Condo

A bright living area is shown, featuring a spacious gray sofa and a wooden coffee table. Large sliding glass doors provide unobstructed ocean views, while a ceiling fan circulates air above. A small dining table with chairs complements the relaxed coastal decor.

4.99 out of 5 average rating, 258 reviews

Beachfront! Newly remodeled! Right on the beach!

Other holiday rentals with a pool

Apartment in Miramar Beach

4.97 out of 5 average rating, 31 reviews

Summer breeze house beach view

4.97 out of 5 average rating, 75 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, 20 reviews

A well-constructed carriage house features a spacious front porch with black railings and rocking chairs. The overhang creates a shaded area, while the driveway leads to the garage beneath. Lush trees surround the house, complementing the gravel pathway and landscaped areas.

Guest house in Milton

Rainbow Land Carriage House

5 out of 5 average rating, 8 reviews

The exterior of the three-story beach home is showcased, featuring a large, inviting pool surrounded by lounge chairs. A spacious deck is visible, with the front of the house displaying double gables and multiple balconies. Lush landscaping is present around the pool area.

Home in Navarre Beach

Private Pool, Steps to the beach, Golf cart

The living area features a spacious sofa adorned with decorative pillows. A coffee table sits in front, and natural light floods in through large windows with blue curtains. The open layout connects to a modern kitchen with bar seating and a welcoming decor element above.

4.93 out of 5 average rating, 54 reviews

Gone Coastal 2BR1BA Mins 2 emerald coast beaches!

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

4.76 out of 5 average rating, 38 reviews

Cozy Poolside Escape

Superhost

Farm stay in Baker

5 out of 5 average rating, 3 reviews

Meant to Bee Farm

A spacious living area features a large 75" smart TV beside a cozy brown sofa. Floor-to-ceiling sliding glass doors open to a private balcony, showcasing expansive views of the Gulf of Mexico. Two wooden chairs on the balcony invite relaxation.