Holiday rentals with a pool in Santa Rosa Island

The image displays a direct view from the private balcony overlooking the sandy beach and the Gulf of Mexico. The soft white sand stretches into the distance, meeting the calm waters with varying shades of blue and green under a clear sky.

4.88 out of 5 average rating, 181 reviews

Relaxing Gulf Front Couple's Retreat*Beach Service

Welcome to Okaloosa island! Come experience gorgeous Direct Beachfront unobstructed views! This studio has everything you need for a fabulous beach getaway! Private balcony. Just seconds to beautiful beach & Gulf. 2 Chairs & Umbrella have been purchased for you w/ full beach service$50/day value (Mar-Oct)for a beautiful beachy day! 4 min drive to dining. Lg pool. LVP flooring*2022*Couch*2022*Premium foam mattress*2022 Spotless w/Low Cleaning Fee! Must be 22 years old to book w/ proof of ID

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!

A light-filled studio features a spacious bed with soft linens and decorative pillows. A comfortable sofa is positioned nearby, and sliding glass doors lead to an outdoor area with views. Light tile flooring complements the warm yellow walls, adding to the inviting ambiance.

4.89 out of 5 average rating, 166 reviews

Ground floor! Waterfront condo at Pirates Bay!

Clean, updated waterfront condo at Pirates Bay in FWB! Excellent ground floor, walkout unit. We have smart locks, allowing for easy self check-in. The patio sits just off the resort pool and just steps to the marina and BBQ grills. Pirates Bay is a wonderful waterfront resort community and the west facing unit allows beautiful sunset views over looking the Santa Rosa Sound. Perfect location for everything in Ft Walton Beach and Destin! Public beach access on Okaloosa Island is a short drive!

A light and airy living space features a comfortable seating arrangement with a sectional sofa adorned with patterned throw pillows. A large tufted ottoman sits in the center, complemented by a textured area rug. Soft lighting illuminates the room, enhancing its inviting ambiance.

4.93 out of 5 average rating, 290 reviews

Oceanfront 3BR/3BA Condo | Steps to Sand & Surf!

Experience the Gulf in a Newly Remodeled Condo! This family-friendly ground-floor unit offers ultimate convenience. The master bedroom has ocean views, a king bed with a pullout trundle. The second bedroom has a king bed with a trundle, and the third has a queen bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

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.

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

4.95 out of 5 average rating, 133 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.

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.

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

Home in Santa Rosa Beach

4.82 out of 5 average rating, 161 reviews

Santa Rosa Beach Canopy House with heated pool

Superhost

The outdoor area features a large pool with a colorful flamingo float, surrounded by lounge chairs. A shaded pergola provides a dining area, with a grill and additional seating nearby. Lush greenery and a wooden fence create a private, relaxing atmosphere.

4.92 out of 5 average rating, 149 reviews

Seas The Moment-Free golf cart-Hot Tub-PrivPool

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

Home in Fort Walton Beach

A waterfront property featuring a private pool surrounded by a spacious yard. A large dock extends into the water, offering areas for seating and easy access for fishing or boating. Lush greenery and palm trees frame the picturesque setting, enhancing the overall outdoor appeal.

4.94 out of 5 average rating, 70 reviews

Waterfront ~Home~ Private ~Pool & Deep dock~ boats

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!

4.99 out of 5 average rating, 100 reviews

Home in Santa Rosa Beach

Fresh Fun Interior | New Golf Cart | Heated Pool

4.91 out of 5 average rating, 128 reviews

A spacious living area is illuminated by natural light, featuring a curved sectional sofa and a glass coffee table adorned with magazines. A sleek fireplace adds a focal point, while a modern dining area and kitchen are visible in the background.

Home in Destin Harbor

Harbor Central Penthouse

Apartment rentals with a pool

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

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.

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.

4.98 out of 5 average rating, 45 reviews

Gulf Front #2002 ETW 3King /3Bath Renovated

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

A private balcony offers stunning views of the Gulf, featuring two turquoise chairs and a table with two cocktails. The tranquil beach and rolling waves can be seen beyond the white railing, with umbrellas lined up along the shoreline.

4.96 out of 5 average rating, 135 reviews

Star Of The Sea

A bright living area is showcased with large floor-to-ceiling windows offering panoramic views of the Gulf. Comfortable seating is arranged around a coffee table, with soft furnishings featuring beach-themed patterns. A ceiling fan adds a touch of coastal charm to the space.

5 out of 5 average rating, 6 reviews

Waterscape- $Million Views from Wrap-Around Balcon

A balcony features two high-back chairs, facing the beach and ocean. Soft waves roll onto the sandy shore, with beach chairs and umbrellas visible in the distance. The clear blue sky and gentle clouds create a serene backdrop.

4.82 out of 5 average rating, 118 reviews

Beachfront! Sand-Sun-Surf on Fort Walton Beach FL

Other holiday rentals with a pool

A balcony view showcases bright blue outdoor chairs and a small table. Below, a spacious pool is surrounded by lush greenery and palm trees, with marina access visible in the background. The serene waters of Santa Rosa Sound reflect the cloudy sky.

4.99 out of 5 average rating, 70 reviews

Soundside Waterfront Condo

A spacious living area includes a leather sofa and coffee table, with a large TV positioned on a wood cabinet. A 7' slate pool table occupies one corner. Large glass doors lead to a balcony, providing natural light and views of the surroundings.

5 out of 5 average rating, 53 reviews

Pool Table, Lazy River & AmazingViews! Destin West

A serene beachfront view showcases the tranquil Gulf of Mexico with gentle waves lapping at the shore. A wooden walkway extends from the condominium to the beach, bordered by soft sand and coastal grass under a clear blue sky illuminated by sunlight.

5 out of 5 average rating, 30 reviews

It's a Shore Thing - Gulf Front - Pets Allowed!

An aerial view captures the expansive Waterscape Resort, featuring multiple engaging pool amenities surrounded by lush palm trees. The ocean's vibrant blue water is visible in the background, with clusters of nearby buildings housing vacation rentals.

5 out of 5 average rating, 13 reviews

Waterscape A202-Emerald Vista-2bd+bunks Ocean View

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

5 out of 5 average rating, 48 reviews

The house is illuminated at night, featuring a two-story design with white siding. Palm trees surround the property, enhancing the tropical ambiance. A welcoming front porch is highlighted, showcasing the inviting architecture and tranquil atmosphere.

Home in Miramar Beach

SUGAR SUGAR steps to beach, pool, shops & dining!

Superhost

5 out of 5 average rating, 3 reviews

Beachside Bliss Haven ~ Corner unit

A beachfront balcony features two turquoise chairs positioned for unobstructed views of the ocean. The calm waves and expansive sky create a serene backdrop, highlighting the natural beauty of the coastal environment.