Holiday rentals with a pool in Crestview

4.99 out of 5 average rating, 100 reviews

Home in Sandestin

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

• 2 Bed/2 Bath/Sleeps 8! (1 King, 1 King, 2 Queen Sleeper Sofas) • Includes 6-Person Golf Cart! • Stunning Bay/Lake/Golf Course Views! • Beautiful Upgrades Make You Want to Stay Forever! • Access to 2 Seasonally Heated Pools! • Located on the Beautiful Sandestin® Golf & Beach Resort! • Washer/Dryer, Cable, and WiFi Included! • Minutes to the Private Beach Access via Golf Cart! Rental and golf cart agreement must be signed within 5 days of booking. Must be 25+ to book & present for stay

Condo in Fort Walton Beach

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!

4.97 out of 5 average rating, 151 reviews

An open studio layout is presented with a spacious king-size bed and a comfortable sofa. A round table sits nearby, while large glass doors lead to a balcony with ocean views. Soft, neutral tones are used throughout, enhancing the serene atmosphere.

Condo in Sandestin

Zen Retreat ON Beach -Golfcart* Hot Tub, SanDestin

8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 3+ nts. NEW Pool & Hot Tub. West Elm furniture & King size bed w/ocean view. Sleek Kitchen w/dishwasher & Keurig. WiFi, 55” smart TV. Washer/dryer. Huge balcony to gaze @ the sea. Enjoy the beach, dining, shopping, trails, golf & entertainment all without leaving the resort. Tram pass & Gym. Perfect for honeymoon, baby moon, girls trip, solo travel or lil family vacay *no animals

4.95 out of 5 average rating, 217 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

SEARENITY is a 3 Bed/ 3 FULL bath single family home located on 30A in Old Seacrest. Enjoy beautiful ocean views and a 3 min/ 0.1 walk (map quest walking) to a quiet, gorgeous beach. Our PUBLIC Beach access is RARE. There is NO PARKING so it is always quieter than any other access points. All beach necessities provided. Secluded back yard with outdoor kitchen and private salt water pool (Heated off season). Well equipped kitchen with coffee bar/regular bar. Balcony with ocean views and sunsets.

4.99 out of 5 average rating, 161 reviews

A bright living area features a spacious white sectional sofa adjacent to a light wood coffee table. Floor-to-ceiling glass doors offer expansive views of the ocean and sky, enhancing the openness of the space. A dining set is visible on the balcony.

Condo in Perdido Key

MELODY OF THE SEA - ON THE BEACH- INCREDIBLE VIEWS

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! Beautifully remodeled and updated! This retreat has the rare double windows to enjoy stunning panoramic sunset views! On the beach (No roads to cross)! Resort has indoor heated pool & outdoor pool & hot tub overlooking the ocean. 2 fireplaces in the living room bedroom for those cozy mild winters. King size bed in the master... nautical bunkbeds with port holes & queen sleeper sofa in the main living areas. Reserve Your Time Away Today

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!

4.96 out of 5 average rating, 198 reviews

The living area features a comfortable gray sofa set, a white coffee table, and a ceiling fan. Natural light enters through sliding glass doors leading to a private patio. An open kitchen with wooden cabinetry and a dining area is visible, highlighted by bar stools at the counter.

Condo in Pensacola Beach

$0 clean fee! Beachside/pool view/king bed/jacuzzi

Perfect little place for couples or small families to get some R&R. This condo has a poolside view in a lovely little complex, and is just one building back from the beach - steps from paradise! The Gulf boasts some of the most beautiful beaches in the world, and this is the perfect location tucked away from the busy crowds but still close to restaurants, activities, live music, national parks, and a world class spa. The condo is well-equipped and recently updated in October 2022. Come enjoy!

A spacious living area is highlighted by a large chandelier and soft-colored furnishings. Floor-to-ceiling glass doors provide a direct view of the ocean, while a round table with decorative centerpiece sits in the foreground. A comfortable seating arrangement complements the serene coastal atmosphere.

4.96 out of 5 average rating, 503 reviews

Beach Paradise - Ocean View - Bonus Beach Service

Beach Service for daily set-up of umbrella & 2 chairs included. Available 3/1/26-11/30/26. Discounts for restricted balcony for construction until January 7th. New bathroom renovation complete. Enjoy the gorgeous ocean view in this spectacular 2 bedrooms + 2 full bathrooms condo (972 sqft). Steps from the private beach. Ranked as one of Destin's Top Resorts. Lagoon pool, ocean-front heated pool, gas grills, work-out room, tiki-bar, gated resort, free parking, WiFi, and 24-hr security.

Condo in Fort Walton Beach

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.

4.94 out of 5 average rating, 118 reviews

An open-concept living area is presented, featuring a combination of comfortable seating and a large Smart TV. Natural light floods through expansive glass doors, which lead to a private outdoor space. Light wood paneling and neutral tones contribute to a calm setting.

Townhouse in Sandestin

BellaVida-Sandestin® 2BR/3BA/Lake-Cart to Beach!

Welcome to BellaVida – your Sandestin® escape! This renovated 2BR/3BA gem sits on the water in a private Beachwalk Villas cul-de-sac, complete with a newer model 6-seat golf cart for exploring Baytowne Wharf, private beaches, pools, and Grand Boulevard. Enjoy a spacious, fully remodeled home with updated bathrooms, modern kitchen, full-sized washer/dryer, and unbeatable proximity to the best of Sandestin®. Perfect for a relaxing or adventure-filled getaway—book your dream vacation now!

Home in Fort Walton Beach

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, 304 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!

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.

4.95 out of 5 average rating, 133 reviews

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.

Popular amenities for Crestview rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 138 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

Superhost

4.82 out of 5 average rating, 161 reviews

Santa Rosa Beach Canopy House with heated 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

4.96 out of 5 average rating, 121 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

5 out of 5 average rating, 100 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

4.99 out of 5 average rating, 100 reviews

New Interior | New Golf Cart | New Year| You?

4.97 out of 5 average rating, 126 reviews

An outdoor pool area is enclosed by a screened patio, featuring a rectangular pool and a hammock for relaxation. Comfortable seating is arranged around a coffee table, with greenery adding a touch of nature. A bar with stools is visible, enhancing the outdoor experience.

Home in Pensacola

Poolside Retreat, Hot Tub, 5 min to beach

Condo rentals with a pool

5 out of 5 average rating, 219 reviews

Majestic Sun A711*Remodeled*Golf Cart*Heated Pools

Condo in Fort Walton Beach

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, 106 reviews

Spacious, elegant, beachfront, w/office

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, 103 reviews

Incredible View | On Beachside | Free Parking

Condo in Santa Rosa Beach

A modern studio space features an open layout with a comfortable sofa and a queen bed. The kitchen area is equipped with stainless steel appliances and bar seating for three. Soft blue accents are present throughout, offering a calm ambiance.

4.98 out of 5 average rating, 165 reviews

Modern Seagrove studio steps from the beach

Condo in Santa Rosa Beach

A clear view of the beachfront pool is presented, surrounded by lounge chairs. Beyond the pool, the private beach stretches along the shoreline, meeting the turquoise waters of the Gulf. The bright blue sky complements the vibrant scene, creating a tranquil atmosphere.

4.96 out of 5 average rating, 116 reviews

Beachfront 30A Private Beach Blue Mountain Paradis

4.99 out of 5 average rating, 216 reviews

A bright living area features light blue walls and large windows adorned with sheer white curtains. A white sofa is paired with a decorative coffee table at the center, while a cozy chair is positioned to the side. Natural light fills the space, creating a welcoming ambiance.

Condo in Seacrest

Updated KING 1 Bdrm Condo Balcony, Baby Gear, Pool

4.99 out of 5 average rating, 124 reviews

A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.

Condo in Pensacola Beach

Beachfront Condo With Pool & Resort Amenities

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

4.97 out of 5 average rating, 31 reviews

Condo in Miramar Beach

Summer breeze house beach view

Apartment in Fort Walton Beach

The inviting living area features a light-colored sofa paired with a patterned coffee table. A large television is positioned on a stylish media console. Natural light filters through nearby windows, highlighting decorative art and creating a warm, welcoming space connected to the dining area.

4.89 out of 5 average rating, 65 reviews

Gulf Island Getaway: 2-BR Beach Condo

A charming bungalow is presented with a light grey exterior and white trim. Two rocking chairs are positioned on the front porch, inviting relaxation. Lush green landscaping enhances the curb appeal. A small decorative sailboat accentuates the entrance, adding a subtle coastal touch.

5 out of 5 average rating, 86 reviews

Flip Flops in Paradise

5 out of 5 average rating, 33 reviews

A newly renovated inground pool is featured, showcasing crystal-clear water under a bright sky. Two reclining lounge chairs are situated partially submerged for relaxation. A large umbrella provides shade beside the pool, and a surrounding grassy area is bordered by a wooden fence and tropical plants.

Home in Navarre

Sandy Toes and Tiki Flows

Superhost

A spacious living area showcases a large wall-mounted television displaying a serene beach scene. Light-colored furniture includes a comfortable sofa and armchairs, complemented by a coffee table. Floor-to-ceiling windows provide expansive views of the ocean, accented by sheer drapes that allow natural light to enhance the space.

4.88 out of 5 average rating, 8 reviews

Gulf Front, Private Balcony, Heated Pool & Hot Tub

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.

Guesthouse in Milton

Rainbow Land Carriage House

5 out of 5 average rating, 7 reviews

The Firefly Poolside Cottage close to all of 30A