Vacation rentals in Santa Rosa Island

A large, inviting swimming pool features colorful floating lily pads and a rope bridge. Surrounding the pool are palm trees and lounge chairs, with poolside umbrellas providing shade. A colorful bar area is visible in the background, enhancing the resort's family-friendly atmosphere.

4.86 out of 5 average rating, 211 reviews

Waterpark Condo with Free Beach Setup & Aqua Pass

Welcome to Waterscape A419! This is a 1292 sqft 2 bedroom, 2 1/2 bath condo with a private bunk room that sleeps 8 people plus a baby. Waterscape is one of the newest and most luxurious direct beachfront resorts in Fort Walton Beach/Destin area. Our Unit is located on the 4th floor with partial beach/ocean views as well as the bay view. The resort has great amenities: 3 amazing swimming pools, a relaxing LAY-Z™ River, 10 gas grills, poolside Tiki Bar, fitness center, and private pristine beach.

A generous balcony features a round table surrounded by four striped chairs, offering ocean views. Two blue lounge chairs are positioned beside the table. The expansive space allows for comfortable relaxation while overlooking the beach and turquoise waters.

4.93 out of 5 average rating, 279 reviews

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA

Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the BEACH. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.

4.98 out of 5 average rating, 128 reviews

Beachfront Bliss! Gulf Waves at The Palms #201

Nestled on shimmering Gulf shores, The Palms #201 invites you to unwind with jaw-dropping oceanfront views. This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat. Steps from the water, this guest favorite blends relaxation and rejuvenation for a home-away-from-home feel. From March through October, we provide complimentary beach service with two chairs and umbrella—a $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

A panoramic view showcases the pristine white sandy beach meeting the azure waters of the Gulf of Mexico. Beach umbrellas line the shore, while a wooden boardwalk leads through lush greenery, providing access to the beach and inviting relaxation in a serene environment.

4.9 out of 5 average rating, 246 reviews

NAUTILUS 2608, Sleeps 6, Amazing Views!

Amazing views of the Gulf of Mexico from this 2 bedroom 2 bath condo, sleeps 6. On the 6h floor of the beautiful Nautilus condominium, you will enjoy the wide balcony with incredible views. Fully equipped kitchen, all linen and beach towels included. Beach service from March 1st until Oct 31st (2 chairs & an umbrella) Additional beach chairs and umbrellas in the condo. Heated pool. Many restaurants in the area. Groceries 5 min away. Special rates snowbirds and military on TDY. 25 yr old min.

A bright living area features a light grey wall with natural lighting from large windows. Two cozy sofas, one in dark grey and the other in a mixed pattern, offer seating. A white coffee table sits in the center, complemented by a decorative rug and a fan overhead.

4.91 out of 5 average rating, 127 reviews

Beach Side- 2Br 2Ba 3bed | POOLS- GEM-BEACH!

Walk to the Beach at Sunset or Sunrise Every Day! 2 pools, indoor pool & outdoor pool next to the White Sand Beach Access, BBQ Area, elevator & fitness room amenity. Come and enjoy Fun & Sun at our condo by the beach! Gorgeous 2 Br 2 Ba condo is an amazingly nice & quiet like open air community on 2nd floor/elevator, balcony view looks over the neighboring county beach access and down the shoreline PERFECT for those summer fun & sunsets! Morning /Afternoon Walk on the 2 miles Santa Rosa Blvd.

Townhouse in Santa Rosa Island

An open living space features a large flat-screen television mounted on a white wall. A comfortable sectional sofa is positioned around a coffee table, complemented by decorative elements such as a plant and books. A sleek kitchen bar with stools enhances the layout, creating a welcoming atmosphere.

4.95 out of 5 average rating, 215 reviews

Beauty & The Beach near Gulf Beaches & Bay

Relax in this calm/stylish getaway within walking distance to the gulf beaches. My home sits next to the boardwalk only a 5 min walk to the beautiful white sands of the Gulf + 1 min walk to the bay/Sound 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

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.

4.94 out of 5 average rating, 126 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

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.

4.98 out of 5 average rating, 130 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.

Apartment in Santa Rosa Island

A spacious living area is highlighted by a blue bedspread on a queen-sized bed and a dark gray sofa. The kitchen area features white cabinetry and modern appliances. Colorful artwork adorns the walls, creating a light and cheerful atmosphere.

4.8 out of 5 average rating, 116 reviews

Our Happy Place

Pack your bags and head to Our Happy Place. Readily equipped with everything you will need for relaxation, fun or adventure. Our Happy Place is situated on the water where you can sit and watch boats go by, or fish from the shore. Take a dip in the community pool that offers plenty of lounger chairs and tables with umbrellas. Just across the street you will find a boardwalk to stoll down to the white sandy beaches where you can soak up the sun and Gulf of Mexico views.

4.78 out of 5 average rating, 131 reviews

Kid-friendly! Lazy River~Skywalk over to beach!

This is a beautiful one bedroom condo plus bunk area located on Bayside of Destin West! The unit comes equipped with a beach cart to make the short walk to the beach even easier! You will love the location of this unit! Freshly painted, with beautifully decor, plus beach towels (2) - you will feel right at home at our 'Salty sandpiper'. With a fully stocked kitchen, washer and dryer, and a lazy river pool - this condo is the perfect place for your beach getaway!

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, 116 reviews

Island Princess 618 | Beach Service Included

Experience the perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

Condo in Fort Walton Beach

4.97 out of 5 average rating, 103 reviews

Stars & Sea•Overlooking Pool & Sound•Sleeps 4

Kick back & relax in this calm, newly renovated ground-level condo on the Sound in Ft Walton Beach! ✨ Highlights: • 🌴 Waterfront views & stunning sunsets • 💦 Large resort-style pool • 🏖️ Minutes to beach access • 🍽️ Walk to local restaurants • 🚗 Easy parking & quiet community 🛏️ Queen bed w/Purple® mattress + Queen memory-foam sofa bed ☕ Kitchenette: Fridge • Air fryer/toaster • Microwave • Keurig •7.5 Miles to Destin

Popular amenities for Okaloosa Island vacation rentals

Free parking on premises

Beachfront

Self check-in

Gym

BBQ grill

Stay near Santa Rosa Island's top sights

Destin Harbor Boardwalk

433 locals recommend

Emerald Grande at HarborWalk Village

42 locals recommend

McGuire's Irish Pub and Brewery Destin

571 locals recommend

HarborWalk Village

562 locals recommend

Gulfarium Marine Adventure Park

570 locals recommend

Crab Island

359 locals recommend

Okaloosa Island beach vacation rentals

A scenic view of the beach at sunset, with the sun dipping below the horizon. Gentle waves lap against the shore, while silhouettes of people can be seen strolling along the sandy beach. The sky is tinted with soft orange and yellow hues, enhancing the tranquil atmosphere.

4.82 out of 5 average rating, 153 reviews

Keeler Island Princess #508 Okaloosa Island Bchfrt

4.87 out of 5 average rating, 151 reviews

A spacious living area is illuminated by large windows, offering views of the surroundings. Comfortable seating is arranged around a coffee table, and a television is positioned nearby. A dining area with a wooden table accommodates seating for six, complemented by a ceiling fan for added comfort.

Condo in Destin

Top-Floor Ocean View • Private Beach Access

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.

4.98 out of 5 average rating, 115 reviews

Spacious, elegant, beachfront, w/office

A bright living area is shown, featuring a comfortable seafoam green couch and accent pillows. A large television is mounted on the wall. A coffee table sits on a patterned blue rug, with a view of the water visible through sliding glass doors that lead to a private balcony.

5 out of 5 average rating, 106 reviews

Beach front Condo with Beach service!

4.98 out of 5 average rating, 120 reviews

Condo in Destin

Incredible Direct Ocean View|2 Pools|Beach Chairs

4.84 out of 5 average rating, 301 reviews

A bright living area features a spacious gray sofa, complemented by a blue and white decorative pillow. Large glass doors open to a private balcony with ocean views. A dining table with white chairs and a chandelier is visible, alongside a wall-mounted flat screen TV and coastal artwork.

Condo in Destin

Majestic Ocean Views, Oceanfront Condo, Renovated!

A scenic view captures the landscaped courtyard of the resort, featuring palm trees and a swimming pool. The background displays condominium buildings against a colorful sunset sky, providing a serene atmosphere. Soft lighting begins to illuminate the courtyard, enhancing the visual appeal.

4.87 out of 5 average rating, 106 reviews

Waterscape 3rd Floor 1 Bedroom - on the beach -

A spacious and inviting living area showcases a large sectional sofa adorned with blue and white accents. Natural light fills the space through expansive sliding glass doors that offer a view of the Gulf. A ceiling fan provides a refreshing breeze while a coffee table and a patterned armchair complete the seating arrangement.

4.97 out of 5 average rating, 110 reviews

Condo With Serene Panoramic Views of the Gulf

Okaloosa Island home rentals

4.96 out of 5 average rating, 141 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, 7 reviews

Its 5 o'clock here

A serene outdoor space features a private pool enclosed by a safety fence. Colorful seating options are arranged on a decorative mosaic patio, complemented by an umbrella providing shade. Lush trees provide greenery in the background, enhancing the peaceful atmosphere.

4.92 out of 5 average rating, 211 reviews

#2 4BR HUGE PET Friendly Home Away from Snow!

Home in Santa Rosa Island

4.57 out of 5 average rating, 14 reviews

Coconut Beach House A

4.83 out of 5 average rating, 116 reviews

1 BR Comfortable Central Location Emerald Elm

A spacious outdoor area features a large swimming pool, surrounded by a concrete deck. Lush greenery provides a natural backdrop, and a few lounge chairs are positioned nearby for relaxation.

4.9 out of 5 average rating, 145 reviews

Relaxing Pool Retreat Near Beaches & Destin!

A collage of the townhome is presented, showcasing a stylish dining area with a wooden table and plush seating, a modern living room featuring a wall-mounted TV, a uniquely designed bunk area with colorful wallpaper, and the exterior highlighting the driveway and garage area.

4.86 out of 5 average rating, 106 reviews

House in Ft Walton Beach near Okaloosa Island *TVs

A game room features a vibrant red pool table, positioned centrally under recessed lighting. Surrounding walls display decorative accents, including a mirror and wall art. A window provides natural light, while a television is mounted on an adjacent wall.

4.92 out of 5 average rating, 156 reviews

Three Forty Eight The Great Escape! (Pet Friendly)

Okaloosa Island cottage rentals

4.96 out of 5 average rating, 112 reviews

On 30A | King beds | 3 min to beach

4.96 out of 5 average rating, 317 reviews

A staircase with wooden railing leads to an upper level, complemented by a vibrant plant mural on the wall. The kitchen area features modern appliances, including a stove and refrigerator, with light cabinets and a tiled backsplash. Natural light brightens the open space.

Cottage in Destin

Two blocks to the beach! Bikes included!

A well-lit exterior reveals a charming cottage nestled among lush greenery. A wooden pathway leads to the entrance, accompanied by vibrant outdoor lighting and dense foliage, creating a serene and inviting atmosphere at dusk.

5 out of 5 average rating, 114 reviews

Historic Smith House, authentic cottage

Cottage in Fort Walton Beach

A cozy living area features sloped ceilings and abundant natural light from large windows. A plush sectional sofa is arranged around a circular coffee table, complemented by a patterned area rug. A single lamp provides additional lighting, enhancing the space's comfort.

4.91 out of 5 average rating, 287 reviews

"Quirky Cottage"

A two-story house with a classic design features a welcoming front porch with multiple white railings. Lush greenery surrounds the property, with palm trees visible. A brick pathway leads to the front door, while a white picket fence encloses the yard.

4.97 out of 5 average rating, 237 reviews

Beach Cottage South of 30a -Steps to Beach & More!

4.81 out of 5 average rating, 122 reviews

The cottage features a grey metal roof and a welcoming front entrance. Lush green hedges and a white picket fence frame the property, while a palm tree adds a tropical touch. A clear blue sky provides a bright backdrop.

Cottage in Miramar Beach

Charming Beach Cottage- with beach service

4.83 out of 5 average rating, 166 reviews

A welcoming entrance features a covered porch adorned with vibrant pink flowers and a birdhouse. Two white chairs are positioned beside a small table, inviting guests to enjoy the serene setting. A decorative wind chime adds a touch of charm to the doorway.

Cottage in Mary Esther

Nature's Nest Cottage on the Sound - Pets Welcome!

A charming beach cottage is featured, showcasing a light-colored exterior with a metal roof and a welcoming front porch. Lush greenery and colorful plants surround the property, while palm trees add a tropical touch. The driveway leads to the entrance, enhancing the inviting atmosphere.