Holiday rentals with a pool in Santa Rosa Island

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 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, 571 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.

A modern living area is showcased with a green sofa and two red armchairs, complemented by light wood flooring. A colorful wall art piece adds vibrancy, while a ceiling fan provides airflow. The open floor plan offers a view into the adjacent dining and kitchen area.

4.95 out of 5 average rating, 106 reviews

Free Chair Service-Beachfront 4th Floor

Beautiful fourth-floor balcony views of beachfront, barrier island chain, and sound area! Exceptionally convenient white-sands beach access and gorgeous emerald waters! Enjoy indoor/outdoor pool and on-site gym. This beach condo is not only fantastically located on the quieter end of Okaloosa Island, but also comes with modern, coastal-themed furnishings. Access the Destin and Fort Walton Beach attractions only a few miles down the street. Includes free chairs and umbrella on the beach!

A spacious living area features a light-colored leather sectional sofa and a circular wooden coffee table, complemented by a plush rug. Large sliding glass doors open to reveal views of the Emerald Coast, with outdoor seating visible on the patio.

4.97 out of 5 average rating, 144 reviews

One Step to the Beach!

"One Step to the Beach" Highlights: - Beachfront Condo at Surf Dweller - First Floor - Pull Up to the Front Door and Unload - Free “Platinum” Beach Service: 2 Beach Chairs, Umbrella + Kayak / Paddleboard access (Mar-Oct) - Two Parking Spaces - 1 King Bed - Master Suite - 2 Queen Beds - Second Bedroom - Cable + Streaming - WiFi - Keurig and Drip Coffee Makers - Seasonal Heated Pool - Tennis/Pickleball Courts - Washer and Dryer in the Condo - Pack n' Play - Shopping / Restaurants Nearby

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

* Huge oceanfront lanai * Free beach service April 1-Oct 31 *Adult/Kiddie pool; tennis *Private office space in the condo *High chair/pack-n-play *Huge 1453 sq ft *Fully stocked kitchen incl. air fryer *Near Destin but WAY less crowded *South facing for sunrise & sunset (seasonal) & sometimes dolphins! *Open the door to your private lanai for REAL white noise of the ocean waves

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.

The image captures a sprawling resort pool area lined with palm trees, inviting lounge chairs, and winding waterways. A mix of tranquil pools is observed, with gentle steps leading into the water and vibrant blue shades reflecting the clear skies.

4.87 out of 5 average rating, 121 reviews

Waterscape 5th Flr -Closest 1 Bedroom to the beach

Enjoy the best courtyard and ocean views from this 5th-floor 1BR condo, the closest 1-bedroom unit to the beach at Waterscape Resort. 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, in-unit washer/dryer, and beach chairs with umbrella stored in the unit. Guests return year after year for the views, comfort, and resort amenities like pools, waterfall, and lazy river.

The image captures an expansive view of the tranquil Gulf of Mexico. Gentle waves roll onto a sandy beach, while a clear blue sky stretches above, dotted with soft clouds. The horizon blends seamlessly with the serene water, creating a calming seaside atmosphere.

4.94 out of 5 average rating, 188 reviews

Sunshine and beach time /Okaloosa Island

CHRISTMAS at the BEACH! Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). Fully furnished, ( USB port outlets, no carpet, stainless appliances, and keyless entry). A one minute walk to the white sand, wifi in the unit, 2 beach chairs, cooler, beach towels, and beach umbrella. Laundry onsite, Tom Thumb next door for items you might need. Everything for a great beach vacation! 683 Nautilus court

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

Islander 705 Studio condo with a beautiful Gulf view on Okaloosa Island. This 7th floor unit sleeps 2 and includes - 1 King bed - 1 sofa sleeper - 1 Full bathroom (glass shower) - Keurig Mini - 1 full kitchen with stove, refrigerator, microwave, dish washer Complimentary beach service 2 chairs and 1 umbrella included March - October! Enjoy amazing views of the Gulf & white sand beaches with the perfect sunset view from the balcony!

A panoramic view of the beach showcases soft white sands meeting the tranquil turquoise waters of the Gulf. Beach umbrellas and chairs line the shore, with a clear blue sky above enhancing the serene coastal landscape.

4.98 out of 5 average rating, 110 reviews

Island Princess 618 | Gulf Views & Beach Service

Experience the ultimate beach getaway at our renovated condo on stunning Okaloosa Island. This beachfront retreat features two spacious bedrooms, two modern bathrooms, and a rare oversized balcony perfect for soaking in the breathtaking views. Relax on the sugar-white sands and take in the emerald-green waters of the Gulf with complimentary beach service, including two chairs and an umbrella, provided from March 1st to October 31st.

A view of the Gulf can be seen through vibrant blooming flowers and palm trees. A wooden pergola is present in the background, with sun loungers visible at the pool area, creating a serene coastal atmosphere.

4.93 out of 5 average rating, 185 reviews

Sea Shell at Sunset Cottages - Beach Service Inc

Sea Shell condo is located in the 19 unit Sunset Cottages complex on Okaloosa Island in Fort Walton Beach, FL. “Gulf Side”, just over 200 steps from the sand, no roads to cross, relaxing on the beach in minutes! The Sea Shell has 2nd floor partial gulf views from the dining room window, and both balconies. Inside is a spacious 750 sq.ft. to lounge and relax including; large great room, large bedroom and bath, condo built in 2000.

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, 279 reviews

Okaloosa Island Top Floor 2BR Beach Condo

Welcome to the Islander unit 707, a cozy beachfront condo located on the seventh (top) floor of the Islander Beach Resort on Okaloosa Island. This charming two-beds, two-bathroom unit has everything you need for a comfortable and relaxing stay. Enjoy stunning views of the Gulf of Mexico from the private balcony or take a short stroll to the white sandy beach just steps away.

Popular amenities for Santa Rosa Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

4.82 out of 5 average rating, 161 reviews

Santa Rosa Beach Canopy House with heated pool

A private pool area is surrounded by lush palm trees and decorative murals. Two lounge chairs are positioned beside the pool, offering a relaxing space. Soft string lights illuminate the scene, enhancing the tranquil evening atmosphere.

4.94 out of 5 average rating, 109 reviews

Book Holiday! Private Beach, Heated Pool, 2 Kings!

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.

4.96 out of 5 average rating, 121 reviews

Sugar Sand Cottage at Destin Pointe

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.

4.96 out of 5 average rating, 197 reviews

Private Heated Pool! Walk 2 Beach!

A charming cottage stands under a clear blue sky, featuring a welcoming front porch with railings. A complimentary six-seater golf cart is parked in front, showcasing comfortable seating and a sleek design. Lush greenery and palm trees enhance the inviting atmosphere.

4.93 out of 5 average rating, 152 reviews

FREEGolfCart!/HEATEDPool!/Walktobeach! Sleeps 10!

The backyard features a private saltwater pool surrounded by lounge chairs and umbrellas for shade. A large swan float is positioned in the water, and a patio area includes a grill, enhancing the outdoor space for relaxation and entertainment.

4.98 out of 5 average rating, 123 reviews

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

A two-story home is surrounded by lush greenery, featuring a pastel exterior and decorative shutters. The entrance is framed by palm trees and well-maintained shrubs. A balcony above provides added charm, while the clear blue sky creates a welcoming atmosphere.

4.95 out of 5 average rating, 208 reviews

Destin's most adored home!

4.99 out of 5 average rating, 100 reviews

Fresh Fun Interior | New Golf Cart | Heated Pool

Apartment rentals with a pool

Apartment in The Village of Baytowne Wharf

A spacious studio is presented, featuring a comfortable sofa and a large bed with light linens. Natural light fills the room through a window, while a wooden coffee table is situated at the center. Ceiling fan and tasteful artwork add to the decor.

4.93 out of 5 average rating, 298 reviews

Cozy Coastal Baytowne Studio Amazing Amenities

4.97 out of 5 average rating, 103 reviews

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.

Apartment in Destin

Incredible View | On Beachside | Free Parking

A private balcony overlooks the Gulf, featuring a round table surrounded by six light-colored chairs. The area is designed for relaxation, with unobstructed views of the beach and water stretching into the horizon. The floor is finished in a cool, muted tone.

4.93 out of 5 average rating, 14 reviews

Nautilus 1601 - Gulf Front 2BD/2BA 6th Floor. Fr

The image captures a panoramic view from the balcony, displaying the bay on the left, the town of Destin in the center, and the beach on the right. Green rooftops of nearby buildings and palm trees are visible in the foreground, contributing to a coastal atmosphere.

4.85 out of 5 average rating, 234 reviews

Destin West V506 - Free Beach Service & Lazy River

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.

4.94 out of 5 average rating, 184 reviews

Beautiful Emerald Beach Condo

4.88 out of 5 average rating, 64 reviews

Beach Side 1/1 Condo Paradise

The living area is equipped with a large sectional sofa and a coffee table, offering a comfortable space for relaxation. Floor-to-ceiling sliding doors provide access to the balcony, allowing natural light to fill the room. A flat-screen television is positioned on a media console, enhancing entertainment options.

4.96 out of 5 average rating, 84 reviews

Island Paradise on Okaloosa Island

A serene waterfront view features calm waters bordered by a grassy area. A black metal bench is positioned on the shore, providing a place to sit and enjoy the scenery. A dock is visible in the distance, enhancing the tranquil atmosphere.

4.83 out of 5 average rating, 166 reviews

Penthouse/Intercoastal waterway/pool

Other holiday rentals with a pool

Apartment in Miramar Beach

4.97 out of 5 average rating, 30 reviews

Casa brezza estiva beach view

A private rooftop space features a hot tub and two chairs, offering expansive views of the beach and ocean. The surrounding area is paved with light-colored tiles, and the railing provides a barrier while allowing unobstructed sightlines of the water.

4.85 out of 5 average rating, 41 reviews

Destin West Villa PH01 ~ Penthouse w/ Hot Tub

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.

Apartment in Destin

4.88 out of 5 average rating, 8 reviews

Gulf Front, Private Balcony, Heated Pool & Hot Tub

Flat in Fort Walton Beach

An open-concept living area features a light-colored sofa adorned with throw pillows, overlooking a modern kitchen with stainless steel appliances. A spacious dining table with blue barstools is positioned near a decorative blue accent wall, while a wall-mounted TV adds to the contemporary decor.

4.96 out of 5 average rating, 45 reviews

Waterfront Getaway w/ Pool Access – Bluefish #6

A private balcony is presented with a table and two cushioned chairs, overlooking the sandy beach and tranquil waters of the Gulf of Mexico. A clear blue sky complements the serene beach setting, providing a picturesque environment for relaxation.

4.95 out of 5 average rating, 42 reviews

314 Island Princess - Beach, Pool, Spa, Balcony!

A spacious balcony offers a stunning view of the ocean and sandy beach. Outdoor seating is provided, featuring a lounge chair and decorative cushions. The horizon displays soft waves, and people can be seen enjoying the beach along the shoreline.

4.95 out of 5 average rating, 80 reviews

"SeaGlass" - Oceanfront with expansive balcony.

A bright living area features a comfortable blue and white striped sofa, accompanied by a patterned armchair. A television is mounted on the wall, and large glass doors open to a private balcony, allowing natural light to fill the space.

5 out of 5 average rating, 35 reviews

Beach Retreat

Two green beach chairs are positioned on the white sandy beach, facing the calm, emerald waters of the Gulf. The clear blue sky stretches above, complementing the serene beach environment.