Holiday rentals in Santa Rosa Island

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Top-rated holiday rentals in Santa Rosa Island

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Guest favourite
Apartment in Fort Walton Beach
4.82 out of 5 average rating, 101 reviews

Destin West Penthouse Bay, Roof Top terrace

This fresh looking/newly remodeled Sandpiper PENTHOUSE Condo offers the best of two worlds. It offers breath taking, direct-shot views of the pristine Choctawhatchee Bay , Lazy River and Zero entry & seasonally heated Water Fall pool. The Hot tubs, New Marina and BBQ pits are right below your two balconies. This is a 1 Bedroom with Bunk Room and 2 baths Penthouse condo on the Bay side of Destin West. The views from the roof-top floor blow away the condos on the lower floors. On site Marina!

Guest favourite
Flat in Fort Walton Beach
4.87 out of 5 average rating, 153 reviews

*Perfect location | Charming beach retreat*

Located a short three minute drive to the beautiful white sand beaches of the emerald coast, and only two minutes from downtown. This bright and well kept condo is the perfect escape that you've been waiting for! Fully stocked with extra towels, beach chairs, and all the standard cookware for your family beach getaway. Our condo was created for your relaxation, enjoyment, and affordability being our highest priorities. Extended stay guests are welcome with huge weekly discounts. No pets policy.

Top guest favourite
A spacious pool area is surrounded by palm trees and lush greenery. Two distinct pools are visible, with lounge chairs arranged on the deck. The soft blue water reflects sunlight, providing a refreshing atmosphere for relaxation.
Apartment in Fort Walton Beach
4.97 out of 5 average rating, 193 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.

Top guest favourite
Apartment in Fort Walton Beach
4.9 out of 5 average rating, 205 reviews

Destin West Villa #V502 Beach Vacation Awaits

Newly updated beach-side 5th floor unit. Renovated bathroom with a large walk in shower. It has one of the best views in the Florida panhandle. A 180 degree view of the emerald waters of the Gulf of Mexico, the Okaloosa Island sand dunes, Destin and Choctawhatchee Bay. Your unit is Gulfside. You are steps away from the white sandy beach, 7 different pools and many restaurants and fun activities to walk to. Relax in the lazy river pool, sunbathe at the beach or spend your day being adventurous.

Top guest favourite
Townhouse in Fort Walton Beach
4.95 out of 5 average rating, 200 reviews

Beauty & The Beach near Gulf Beaches & Bay

Relax in this calm/stylish getaway within walking distance to the gulf beaches. Our home sits next to the boardwalk only a 5 min walk to the beautiful white sands of the Gulf plus 1 min walk to the bay! Near restaurants/bars and fun family activities You’ll love the location/convenience of Okaloosa Island near beach access #1 Destin- 10 min drive Ft Walton Convention Center-5 min drive Downtown Ft Walton -10 min walk FWB Pier -10 min walk ✈️ Destin / Fort Walton Airport - 20 min drive

Guest favourite
A spacious bedroom features a king-size bed dressed in soft linens, accompanied by two bedside lamps. Large glass doors provide access to a balcony, allowing natural light to brighten the room. A comfortable chair is positioned nearby, enhancing the inviting atmosphere.
Flat in Fort Walton Beach
4.97 out of 5 average rating, 149 reviews

Beach condo with Gulf view, heated pool and gym!

Enjoy your time at peaceful Heron's Shore at seacrest condominiums. You will love the soft white sand beach and the warm emerald waters that are accessed via the boardwalk. The pool is heated when the weather is cool. Get you exercise on the beach or in our Gym. Use the elevator to bring your luggage to our 4th floor suite and park your vehicle in the underground parking. Dine at nearby restaurants or BBQ. Visit Crab Island & just have a wonderful time at Heron's Shore on Okaloosa Island.

Guest favourite
A clear view of the beach and ocean can be seen from the balcony, with lounge chairs and umbrellas set up along the shoreline. A spacious pool area, filled with sun loungers and palm trees, is visible below, complementing the scenic ocean backdrop.
Apartment in Fort Walton Beach
4.95 out of 5 average rating, 110 reviews

DestinWest G405 Kid-friendly/oceanview/Lazyriver

[new patio furniture] Destin West Resort Gulfside 405 (2mins to the beach and pool) ~ 1 Bdr + 1 bunkroom with 2 full baths, Sleeps 6 ~ great ocean view ~ free beach service: 2 chairs & 1 umbrella (seasonal: 3/1 - 10/31, 9am-5pm) ~ 1 King Bdr with a private bathroom ~ 1 bunk room (2 twin beds, each with its own TV) with a private bathroom ~ 1 Q pullout sleeper ~ pack n play ~ 4 smart TVs ~ full kitchen stocked with cookware (Keurig and a traditional coffee maker). ~ washer/dryer

Top guest favourite
A spacious living area features a sectional couch complemented by a round coffee table. Warm wood accents are highlighted by overhead pendant lighting. The adjoining kitchen showcases a large island with bar seating, while a dining area in the background is arranged with a large table.
Home in Ferry Park
4.99 out of 5 average rating, 115 reviews

Stunning updated 4 bedroom home. 8 mins from beach

Escape with family or friends to this stunning, fully renovated coastal home. Only a short drive from the Gulf Coast's pristine beaches, this cozy home offers all the comforts of home and conveniently located near downtown FWB. Walk up the street for public water access to view the bay. Ample parking in the driveway for your boat, trailer or RV. Enjoy the large fenced-in backyard, perfect for outdoor entertaining. Book now and experience the best of Florida's Emerald Coast.

Guest favourite
A bright living area features a comfortable sofa and armchairs, complemented by a wooden coffee table. Large glass doors provide access to a private balcony, showcasing ocean views. Soft natural light fills the space, enhancing the tile flooring and the neutral color palette.
Apartment in Fort Walton Beach
4.87 out of 5 average rating, 122 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.

Top guest favourite
A clear swimming pool is shown, with a depth marked as 3 feet. Surrounding lounge chairs are visible, along with several umbrellas providing shade. The well-maintained area is bordered by a white fence, with palm trees and buildings in the background under a bright blue sky.
Apartment in Destin
4.93 out of 5 average rating, 263 reviews

3 Min Walk to the Beach, Beach Svc, Sandpiper Cove

***Beach service at our private beach for 2 included**** A beautifully decorated studio condo that sleeps 4 comfortably. It includes a queen size bed and queen size sleeper sofa with a memory foam mattress. Not to mention a breakfast bar and 55” TV with surround sound. You can stand on the back deck and see views of the sugary white sand beaches that are right across the street from our place. Beach service at our private beach for 2 included from March-October.

Guest favourite
A bright living area features coastal-themed decor, including a soft beige sofa and armchair. Large glass doors open to a balcony with ocean views. Light cream walls are complemented by a colorful piece of art. A coffee table sits center stage, accompanied by a soft area rug.
Apartment in Fort Walton Beach
4.91 out of 5 average rating, 139 reviews

Ocean Views at Waterscape Resort!

Experience everything the stunning Emerald Coast has to offer while staying in our beautifully updated condo, with expansive ocean views including everything you need for a comfortable stay! Enjoy the Waterscapes resort amenities including direct beachfront access, beach chairs & umbrella, lazy river, zero entry pool, kids water play area, a separate heated pool for the cooler months, hot tubs, propane grills, a full gym, on site tiki bar, and free gated parking.

Top guest favourite
A dining area is set for four, featuring white plates and glasses atop a wooden table. In the background, large windows provide a view of the Gulf, while coastal-themed decor, including a lighthouse figurine, adds a touch of beach ambiance.
Apartment in Fort Walton Beach
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 holiday rentals

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$182 SGD$191 SGD$257 SGD$265 SGD$272 SGD$332 SGD$357 SGD$252 SGD$228 SGD$220 SGD$198 SGD$196 SGD
Avg. temp12°C14°C17°C20°C24°C28°C29°C28°C27°C22°C16°C13°C

Frequently Asked Questions

  • What are the best places to stay in Okaloosa Island?

    Okaloosa Island has a range of beachfront rentals, family homes, and cozy condos for travelers. Many stays sit near beaches, local parks, and dining, creating easy access to outdoor activities and Gulf Coast sunsets.

  • What are the best things to do in Okaloosa Island with kids?

    Families often explore the beaches, watch sea life at Gulfarium Marine Adventure Park, or play in waterfront parks. Interactive exhibits and open spaces around the island invite curious kids to learn and have fun.

  • What are some of the best things to do in Okaloosa Island?

    Swim or relax on the soft Gulf beaches, discover marine life at Gulfarium Marine Adventure Park, and stroll along Okaloosa Island Boardwalk for dining and shops. Outdoor enthusiasts frequently enjoy fishing, kayaking, and paddleboarding nearby.

  • How is the weather in Okaloosa Island?

    Okaloosa Island has mild winters around 44–63°F (7–17°C) and warm, humid summers reaching 75–92°F (24–33°C), with frequent rainfall in summer months. Lightweight clothes, sun protection, and rain gear work well for a visit.

  • What are the best places to visit in Okaloosa Island?

    Explore Okaloosa Island Boardwalk for dining and shops, walk sandy stretches along public beaches, and discover marine life at Gulfarium Marine Adventure Park. Locally rooted festivals sometimes highlight arts and Gulf Coast traditions.

  • What are some hiking trails in Okaloosa Island?

    Okaloosa Island has nature paths winding through local parks and beachside areas, where visitors enjoy birdwatching and coastal walks. Nearby reserves and waterfront boardwalks often feature gentle trails suitable for many activity levels.

  • What are some family activities we can do in Okaloosa Island?

    Pack a picnic for the beach, explore interactive exhibits at Gulfarium Marine Adventure Park, or try mini-golf near the Boardwalk. Families often enjoy paddleboarding and beach games on stretches of open sand.

  • What are some of the best day trip ideas from Okaloosa Island?

    Explore nearby nature reserves for hiking or birdwatching, visit vibrant markets in local coastal towns, or enjoy art galleries and seafood restaurants just outside the island. Beach parks and water activities are frequently suggested in the region.

  • Are there any pet friendly accommodations available in Okaloosa Island?

    Many places to stay on Okaloosa Island welcome pets. You can explore stays around local parks and neighborhoods that prioritize pet-friendly policies; be sure to check individual property guidelines for details.

  • What are some local tips for visiting Okaloosa Island?

    Bring reef-safe sunscreen, light layers, and comfortable shoes for beach walks and boardwalk exploring. Many visitors pack reusable water bottles and plan indoor activities in case of rain during humid months.

  • What is Okaloosa Island known for?

    Okaloosa Island is known for its white sand beaches, locally rooted marine wildlife experiences, and casual waterfront dining. Visitors frequently enjoy its family-friendly atmosphere, scenic boardwalk, and access to Gulf Coast nature.

  • What are the best hidden gems to explore in Okaloosa Island?

    Seek out quiet stretches of beach, local art installations around the Boardwalk, and smaller parks where pelicans and local birds can be spotted. Some visitors explore seasonal pop-up markets for regional crafts and flavors.

  • What are the best foods to try in Okaloosa Island?

    Fresh Gulf seafood is frequently suggested, including shrimp, oysters, and grouper. Locally inspired treats such as key lime pie and classic po' boy sandwiches are popular meal options at beachfront eateries.

  • What should I bring for a trip to Okaloosa Island?

    Pack lightweight clothing, swimsuits, reef-safe sunscreen, and a hat for sun protection. Beach towels, water shoes, and rain jackets are useful, especially in summer months when showers are frequent.

  • What is the nightlife in Okaloosa Island like?

    Okaloosa Island has laid-back nightlife, with casual bars, waterside restaurants, and seasonal events near the Boardwalk. Live music and relaxed patios often attract both locals and visitors for evening gatherings.

  • What are the most popular events or festivals in Okaloosa Island?

    Seasonal festivals around Okaloosa Island Boardwalk often feature local music, seafood, and art, while summer beach events bring communities together. Late spring and holiday weekends are common anchors for gatherings and entertainment.

  • Are there family friendly vacation rentals in Okaloosa Island?

    Many homes and condos on Okaloosa Island are set up for families, with easy access to beaches, parks, and local attractions. Features such as full kitchens and outdoor spaces are frequently available for group stays.

  • When is the best time to visit Okaloosa Island?

    Spring and early fall are often recommended for pleasant temperatures and slightly fewer crowds. Summers are popular for beach days, though humidity and rainfall increase, while winters are cooler but still inviting for outdoor walks.

Quick stats about holiday rentals in Santa Rosa Island

  • Total holiday rentals

    Explore 2,830 holiday rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 65,950 verified reviews to help you choose

  • Family-friendly holiday rentals

    2,010 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 190 rentals that welcome pets

  • Holiday rentals with a pool

    2,620 properties feature pools

  • Rentals with dedicated workspaces

    1,640 properties have a dedicated workspace

  • Wifi availability

    2,810 of Santa Rosa Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Free parking on premises, Beachfront and Self check-in across Santa Rosa Island rentals

  • 4.7 Average rating

    Santa Rosa Island stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Santa Rosa Island’s top spots include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park and Crab Island

Destinations to explore