Holiday rentals with a pool in Santa Rosa Island

A panoramic beachfront view showcases a stretch of white sand leading to calm, clear waters. Chairs are arranged along the beach, and a refreshing swimming pool is visible in the foreground. The scene is framed by a balcony railing, enhancing the coastal experience.

4.84 out of 5 average rating, 109 reviews

Sea Oats*Beachfront View!2Bdr/2Bath, Sleeps 6

-Full beachfront view on the 4th floor with a balcony -2Bdr/2Bath: 1 king size, 2 twin size, 1 pull-out sofa-sleeps 6. 2 full bathrooms -Fully equipped kitchen -Free Wi-fi,Smart TV -Beach service (seasonal) -Outdoor swimming pool -Communal jacuzzi -Fresh linens,towels,essentials -Washer/Dryer -Grilling area -Communal workout room -Close to dining and shopping/peer -2 free parking spots -Close to Gulfarium -Close to Destin/Crab Island *By booking you agree to Short Term Property Rental Agreement

A bright studio room features a spacious bed with decorative pillows and a cozy blanket. A comfortable sofa is positioned nearby, and a small dining area is visible. Large sliding glass doors open to a balcony, allowing natural light to fill the space.

5 out of 5 average rating, 118 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 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

Welcome to "The Star Of The Sea", Island Princess #312. Enjoy Gulf front views of the aqua blue waters of the Gulf with its sugar sand beaches from our beautifully decorated condo. Private balcony with access from family room and Master Bedroom. Fully stocked kitchen to prepare fabulous meals while taking in the views of the Gulf from the kitchen and dining area. Both master suites boast of comfort and access to private baths with full shower and tub amenities. Flat screen TV's in every room.

A serene twilight view captures the sky filled with clouds reflecting subtle shades of orange and blue. The marina lights twinkle along the water's edge, while the horizon highlights an array of colors as day transitions into night.

4.97 out of 5 average rating, 194 reviews

Waterfront Studio • Santa Rosa Sound • Sunsets

Enjoy breathtaking views of the Santa Rosa Sound and marina from your private top-floor balcony in this waterfront studio. Whether you're sipping coffee at sunrise or watching vibrant sunsets each evening, this spot delivers unforgettable costal charm in a quiet, peaceful setting. Perfect for couples or solo travelers, the studio features a full bath with tile shower, well-equipped kitchenette and sparkling pool. Gulf beaches are a just a short drive away. Free parking and easy self check-in.

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, 197 reviews

Sunshine and beach time /Okaloosa Island

Plan your SUMMER at the BEACH! SNOWBIRDS message us for a monthly rate (Oct-Feb). Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). (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 scenic view of the Gulf of Mexico is captured from a private balcony. The image showcases soft waves and sandy beachfront lined with umbrellas and beach chairs. Tropical palm trees frame the foreground, while a well-maintained pool area is visible below.

4.81 out of 5 average rating, 139 reviews

Cheery Condo-Free Beach Service-Direct Ocean View!

Let your cares literally drift away in this relaxing, kid-friendly, beautifully decorated condo with a King bed w/bath + twin/twin bunk area w/bath - Queen LR sleeper sofa. Enjoy stunning views of the Gulf of Mexico and pool area from your private balcony. We invite you to enjoy your special vacation at this perfect Emerald Coast paradise. Free beach service (2 chairs and umbrella) is INCLUDED! (March 1-Oct 31). *Note - Okaloosa County Tourist Tax of 6% will be applied to this booking.

A view showcasing a lazy river surrounded by lush palm trees and a spacious pool area. The ocean is visible in the background, with several lounge chairs scattered throughout the landscape. Modern resort buildings are positioned in a welcoming arrangement, enhancing the tropical atmosphere.

4.83 out of 5 average rating, 102 reviews

DestinWest Pelican Bayside, Lazy River, Hot Tub.

Master bedroom with bathroom, bunk room with bathroom (the bunk room has one bunk bed and no door), sofa sleeper. Balcony with lazy river and bay view. You will find everything here from Lazy River, seven pools (one heated, one with waterfall), hot tubs, zero entry pool, gym, bbq area. Next door is an arcade with virtual reality, bar and food. You have access to swim and play in both the ocean and the bay. It is a short walk to the Okaloosa boardwalk for shopping, restaurants and fun

A light blue bedroom features a spacious bed dressed in a colorfully patterned quilt. Accents include two bedside tables with lamps, a stylish chair, and a window that allows natural light to brighten the space. Decorative beach-themed art complements the serene atmosphere.

4.96 out of 5 average rating, 126 reviews

Retreat by the Sea at Seacrest Condo

Welcome to Retreat by the Sea. This studio is at Seacrest Condominiums located directly on the beach on beautiful Okaloosa Island in Fort Walton Beach six miles from Destin. Relax on the balcony and enjoy the beautiful views of the Gulf and amazing sunrises and sunsets. You have direct access to the beach and all the amenities that the condo has to offer including indoor/outdoor pool, gym and bbq area. This amazing studio also has a kitchenette, mini-refrigerator and private laundry.

A balcony features a dining table set with two glasses and a bottle, overlooking the beach. Lounge chairs and umbrellas are visible on the sandy shore, with the Gulf of Mexico's turquoise waters in the background, highlighting direct beach access.

4.95 out of 5 average rating, 146 reviews

Lovely beach-front condo with free beach setup.

As soon as you enter our 3rd floor beachfront condo, you will leave all your cares behind and unwind while enjoying a direct view of the Gulf of Mexico. You can walk to the beach straight out of the building, no need to cross any roads. Many updates done in March 2021: brand new queen size sleeper sofa bed, brand new stainless steel refrigerator, range, dishwasher and microwave, brand new furniture, new paint, new flooring, and brand new TV's. We have Netflix and high speed WiFi.

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, 123 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.

A round glass table is surrounded by four comfortable chairs on a private balcony. The beach extends below, with soft white sand meeting the calm turquoise water. A pier can be seen in the distance under a clear blue sky.

4.96 out of 5 average rating, 120 reviews

Beachfront-Top Floor-West Corner-Free Bch Bch+ Gym

If you’re wanting a vacation where you can sit on your private balcony and enjoy colorful sunsets, sweeping views of the gulf, dolphins playing in emerald green water, seagulls floating by on warm tropical breezes, you need look no further! Welcome to the best of Destin West Gulf Front! This top floor, direct gulf-front condo corner condo offers the perfect vacation spot for that special vacation time. FREE BEACH SERVICE and FITNESS ROOM PROVIDED!

4.97 out of 5 average rating, 101 reviews

Beachfront condo with views

Gulf Dunes 105 – Gulf‑Front & Beachfront Feel the island vibes in this updated 1‑bed, 1.5‑bath condo on Okaloosa Island! Sleeps 6 with king bed, hallway bunks, and sleeper sofa. Enjoy a private balcony with Gulf views, direct beach access, pool, and free beach service (Mar–Oct). Walk to the Boardwalk for food and fun. Perfect for couples and small families. Heated pool 84–85 degrees (Nov–Mar).

Popular amenities for Santa Rosa Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An open living space features a well-equipped kitchen and a cozy seating area. A balcony offers views of the lake, while the bedroom showcases light-colored bedding against a colorful accent wall. Nearby, the ocean and beach properties can be seen along the waterfront.

4.83 out of 5 average rating, 120 reviews

Destin - Beach and Gulf View - 5A

4.94 out of 5 average rating, 109 reviews

Destin Retreat: Oceanview Poolside Luxury Condo

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.

4.93 out of 5 average rating, 113 reviews

Spring Break! 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, 128 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.

4.97 out of 5 average rating, 202 reviews

Walk to Beach · Private Heated Pool · Fenced Yard

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.

5 out of 5 average rating, 107 reviews

Private Pool - Golf Cart - Block to Beach - Destin

4.96 out of 5 average rating, 152 reviews

The exterior of the Mediterranean home is displayed, featuring stucco walls and ornate architectural details. Lush palm trees and manicured landscaping frame the property, while a scenic road runs alongside. The inviting entrance showcases a balcony with decorative elements, enhancing the overall elegance of the design.

Home in Miramar Beach

Oceanview | Pool | Private Beach | Golf Cart

4.91 out of 5 average rating, 141 reviews

Home in Mary Esther

Emerald Oasis: Hot Tub + Sleeps 18 + Pool+ Grill

Apartment rentals with a pool

An aerial view of a beachfront pool area is presented, showing a rectangular pool surrounded by white lounge chairs and shaded areas. The sandy beach is visible just beyond the pool, with a wooden boardwalk leading to the shore.

4.96 out of 5 average rating, 105 reviews

Beach Penthouse on Okaloosa Island in FWB, FL

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, 43 reviews

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

A spacious studio unit features a comfortable bed with light bedding and decorative striped accents. A seating area includes a grey sofa and a small table set, overlooking large glass doors that open to stunning ocean views. A neutral color palette enhances the coastal ambiance.

4.97 out of 5 average rating, 98 reviews

Gorgeous Gulf Front condo with amazing views!

Superhost

A balcony view showcases the expansive Gulf of Mexico with calm waters and a clear sky. A round glass table is set with a cheese platter, fruit, and drinks. Two black wicker chairs frame the table, inviting relaxation while enjoying the scenic beachfront.

Apartment in Destin

4.85 out of 5 average rating, 150 reviews

19th Floor Pelican Beachfront with Ocean View

Superhost

A private balcony features a round table surrounded by four beige chairs. Beyond the railing, views of the sandy beach and emerald waters are visible, with umbrellas dotting the shoreline under a blue sky.

4.88 out of 5 average rating, 8 reviews

Nautilus 1306 Gulf Front 2 BR/2 BA 3rdFL. Free Be

A view from the balcony reveals a boardwalk leading to the beach, flanked by palm trees. The ocean is visible in the distance under a clear blue sky. Multiple parked cars are situated in the foreground, with a beachside building peeking through.

4.98 out of 5 average rating, 65 reviews

2 Bedroom Condo on the Beach at Okaloosa Island

An aerial view of a resort-style condominium showcases a large swimming pool surrounded by palm trees and lounge chairs. The multi-story building, featuring multiple balconies, is situated near the water, with the coastline visible in the distance under a clear blue sky.

5 out of 5 average rating, 42 reviews

Gulfside Gem V306 (Heated Pool & Hot tubs)

4.95 out of 5 average rating, 146 reviews

Beachside-Top Floor-Pools-Free Bch Svc & Gym

Other holiday rentals with a pool

A small outdoor table is set with two cups and a plate of fresh fruit and a bagel. In the background, a view of the Gulf of Mexico is visible, with tall grass and a palm tree framing the beachfront setting.

4.96 out of 5 average rating, 78 reviews

9 Unit Building, Private Pool, Gulf Front View

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, 57 reviews

Unit #6 Waterfront + Heated Pool and Spa Access

Flat in Fort Walton Beach

5 out of 5 average rating, 12 reviews

Island Princess 608 Gulf Front w/Beach Service

4.97 out of 5 average rating, 88 reviews

Stars & Sea•Beautiful Waterfront Condo•Sleeps 4

5 out of 5 average rating, 29 reviews

Top Floor Waterfront View Studio

4.95 out of 5 average rating, 103 reviews

The image shows a stunning beachfront view featuring a clear, turquoise sea and soft white sand. Colorful beach umbrellas and chairs line the shore, while elegant beachfront properties are positioned in the background, emphasizing the relaxed coastal atmosphere.

Apartment in Destin

308 Gulf Views • SUPER HOT Special Book May 1st

The rooftop terrace features a private hot tub with water gently rippling. Expansive views of the beach and bay are visible against a backdrop of dramatic clouds and the setting sun, casting soft golden light across the scene.

4.97 out of 5 average rating, 30 reviews

Destin West Villa PH04~ Hot Tub,on Rooftop Terrace