House holiday rentals in Santa Rosa Island

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, 163 reviews

Three Forty Eight The Great Escape! (Pet Friendly)

The perfect location for a Florida getaway. Spacious house on a quiet street, in close proximity to; Choctawhatchee Bay, a public access beach (2 miles), Uptown Station and downtown Fort Walton Beach for shopping, dining, and libations. Destin is just a $15 Uber/Lyft ride across beautiful Okaloosa Island where you can enjoy all the festivities the famous HarborWalk has to offer. Kids and pets welcome, please inquire regarding long-term off-season rental. Thanks for looking, hope to see you soon!

A comfortable living area features a sectional sofa with a light throw draped over it. A coffee table sits in the center, accompanied by a large TV mounted on a wooden stand. Natural light pours in through two windows adorned with white blinds.

4.86 out of 5 average rating, 133 reviews

The Oasis! Charming 3BR Near All The Best Beaches!

We open our doors to our guests! Our home is filled with love, joy, and passion. You'll feel as if you were at an enchanted five-star resort, where all your stresses just magically melt away. Not to mention, Okaloosa Island and Destin are just under 10 miles away! Also perfectly centralized inbetween both Eglin and Hurlburt field. Perfect for families, travelers, couples, events, or anyone who loves the crystal blue waters & white sands of the Emerald Coast Your home away from home awaits!

4.95 out of 5 average rating, 116 reviews

Private Beach/King Beds/Ocean Views/Fire Pit

Get your feet sandy at the private beach! Escape to a lavish waterfront retreat nestled along the pristine shores of the Gulf of Mexico. Sea Esta #5 is a luxury 3-story townhouse that boasts breathtaking panoramic views and direct access to your own private slice of sandy paradise. Indulge in the expansive living space of our 4-bedroom, 4-bathroom townhouse where each floor is meticulously designed for both relaxation and entertainment...this will be a property you will never want to leave!

The living area features a comfortable sofa facing a large television mounted against a light-colored wall. An open kitchen with modern appliances is visible, complemented by a wooden island with seating for four. Warm wooden tones and elegant flooring enhance the space.

4.84 out of 5 average rating, 134 reviews

House 5 min to Beach, Fire Pit, Deck, Pickleball

Welcome to your perfect getaway, just 5 minutes from the beach, with shopping and waterfront dining at your doorstep. Unwind in this charming beach town rental that is perfect for entertaining with an outside deck equipped with a grill, TV and a fire pit. Explore Fort Walton Beach’s vibrant shopping scene, indulge in local flavors at nearby restaurants, nightlife after dark and return to relax in style. Everything you need is at your fingertips. Book now for an unforgettable coastal escape!

The backyard area features a private pool surrounded by lounge chairs and a paver patio. Palm trees add a tropical touch beside the home, which is illuminated against a twilight sky. A barbecue grill is visible, along with a seating area for outdoor relaxation.

4.97 out of 5 average rating, 138 reviews

Pool, Golf Cart, Fire Pit, & Walk to Beach

★ 3 story Destin home walking distance to Private Beach * 2500ft² / 230m² home * 3rd floor with 360° views and peekaboo views of the ocean * 3 min walk to the private beach and 6 min walk to Crystal Beach * Private pool + backyard oasis (fire pit and more) * 6-seater Golf Cart * Onsite parking for 5+ cars * 5 min drive to Destin Commons with Restaurants & Arcade * 10 min drive to Destin Harbor and 15 min drive to Crab Island * Fully stocked and equipped kitchen * Onsite washer + dryer

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, 149 reviews

Sugar Sand Cottage at Destin Pointe

This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.

5.0 out of 5 average rating, 118 reviews

Home in Mary Esther

Serenity on the Water-Dock/Water -No cleaning Fee

NEW DOCK AND WATERFRONT COMMON AREAS Peaceful, quiet retreat away from the condos and traffic. Beautiful views of the Santa Rosa Sound. Bring your boat. Water and dock access (only shared with the owners). Short boat ride from Crab or Spectre Islands. Close to shopping, food, Santa Rosa Island and Destin. This beautiful 2BR/2.5BA with great water views and water access. One street from a public boat launch. Convenient Boat parking Enjoy crabbing or fishing night or day.

4.82 out of 5 average rating, 144 reviews

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

This family fun home has a 2 story super fast custom water slide, large pool, (extra charge to heat pool) swim up bar, outdoor tiki hut bar with sink and gas grill, charcoal grill, fire pit, sandy beach, dock, boat slip, (no boat lift) paddle boards. Private suite with kitchen & bathroom on lower level with private access leading out to bay. bring your own fishing gear if you like to fish. Home is a labor of love and has brought so much joy to our family & hopefully to yours.

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, 142 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.

The outdoor area features a non-heated swimming pool surrounded by a concrete patio. A small table with chairs is positioned nearby, offering a space for relaxation. Lush greenery provides shade, and a seating area with chairs is visible on the lawn.

4.89 out of 5 average rating, 338 reviews

#1 4BR HUGE PET Friendly Home Away from Snow!

Modern house w/ 2 master bedroom suites with own bathroom and 2 additional rooms sharing a bathroom. Welcome to the emerald coast paradise! You have the best of both worlds, Okaloosa island and the night life are only less than 3 miles away, the beautiful sugar sand beaches are only couple miles away, and you have your own pool (non-heated) in the backyard if you just want to relax and get your tan on! Shopping outlets are near by! Great restaurants around to choose from!

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.

4.96 out of 5 average rating, 160 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 exterior of a spacious beach house is showcased, featuring a distinct blue roof and white siding. Lush palm trees surround the property, while a pool is visible in the fenced backyard, accompanied by a seating area. Ample parking is available beneath the house.

4.95 out of 5 average rating, 102 reviews

Destin Pointe | Private Pool + Hot Tub | 2 Beaches

• 🏖 2-min walk to 2 private beaches • 💦 Private heated pool & hot tub • 🛏 Sleeps 10 | 3 king bedrooms + bunk room • 🌊 3 community pools, including Gulf-front infinity pool • 🚲 4 bikes + 2 paddleboards • 🏖 Beach service, chairs, toys & wagon included • 🔒 Gated Destin Pointe community • 🎣 Walk to snorkeling & fishing • 🍽 Minutes to restaurants & shopping • 🚗 Parking for 4 vehicles • 👶 Pack 'n Play • 🔥 Gas grill • 🏝 No busy roads to cross to reach the beach

Popular amenities for Santa Rosa Island house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view displays the gated community and its proximity to the coastline. The layout includes a mix of residential homes and palm trees, with a clear path marked for the gated beach access leading to the expansive sandy beach and ocean.

4.89 out of 5 average rating, 103 reviews

5 Min Walk to Private Beach | Luxury Remodel

A two-story white house is depicted with a paver driveway leading to the entrance. A 6-seater golf cart is parked in front, surrounded by green landscaping including palm trees. The home presents a welcoming facade, featuring a covered porch and multiple windows.

4.96 out of 5 average rating, 137 reviews

All you need! Location | Golf Cart | Walk to Beach

A private backyard oasis is highlighted, featuring a heated saltwater pool and an inviting fire pit surrounded by oversized Adirondack chairs. The space is enhanced by bistro string lighting, and a colorful flamingo float rests near the pool, creating a warm atmosphere for relaxation.

4.98 out of 5 average rating, 130 reviews

Pet-Friendly-Pvt Heated Pool-Hot Tub-Fire Pit-6min

4.84 out of 5 average rating, 123 reviews

Summer Specials *Fully Loaded* Pool & Hot Tub

A charming beach house with a light-colored facade is framed by greenery. A paved driveway leads to the entrance, flanked by two beach cruiser bikes and a small outdoor seating area with a table. Sunlight filters through the trees, enhancing the inviting appearance.

4.95 out of 5 average rating, 211 reviews

Small Waves-30A beachhouse w golf cart/neighb pool

4.89 out of 5 average rating, 157 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

4.93 out of 5 average rating, 55 reviews

The multi-level home features a light-colored exterior with a rooftop and covered porches. Bright red doors create a striking contrast against the white facade. A private heated pool is visible beneath the home, surrounded by palm trees and outdoor seating on the porch.

Home in Okaloosa Island

1 Fish 2 Fish, Private Pool Home, Pet Friendly

4.88 out of 5 average rating, 17 reviews

FWB Waters Retreat Min to DT, Boat Ramp, & Beach

Weekly house rentals

5.0 out of 5 average rating, 76 reviews

Magnolia Holiday House

4.75 out of 5 average rating, 4 reviews

Home in Okaloosa Island

Blue Heron Bay 205 Okaloosa Island Destin Florida

4.97 out of 5 average rating, 36 reviews

Gorgeous Views & Pristine Pool! Walk to downtown!

5.0 out of 5 average rating, 15 reviews

Bungalow One Eleven | FWB Coastal Retreat

4.96 out of 5 average rating, 54 reviews

An outdoor area is presented featuring a paved patio with ample space. A covered seating area with comfortable furniture is visible beside a BBQ grill. Lush greenery and a wooden fence provide privacy, enhancing the space's functionality for gatherings.

Home in Mary Esther

Secret Beach Luxury Hideaway. Home near beach.

A brick two-story building with a welcoming pathway made of pavers leads to the entrance. The front yard is landscaped with pebbles and bordered by greenery, providing a relaxed outdoor space. The entrance features a bright door complemented by a small seating area.

5.0 out of 5 average rating, 25 reviews

Sherm-Inn

The image displays a collage featuring four areas of the home: a cozy bedroom with soft bedding, a spacious living area with comfortable seating and ceiling fan, a relaxing bathroom with a soaking tub, and a modern kitchen with a large island and ample cabinetry.

4.86 out of 5 average rating, 59 reviews

Seabreeze • 3Bed 2Bath • Mins from Eglin/Hurlburt

A cozy living area is furnished with a light-colored sofa and a round coffee table made of wood. A dark furniture unit holds a large flat-screen TV. Soft natural light enters through glass doors, and a large mirror reflects the space, enhancing the inviting ambiance.

4.97 out of 5 average rating, 62 reviews

BRAND NEW! Spacious Coastal Getaway #4

Private house rentals

A spacious backyard features a private pool surrounded by a grassy area, with lounge chairs positioned for relaxation. A covered patio offers seating for guests, while a large tree provides shade. The home structure is positioned nearby, enhancing the outdoor retreat.

4.85 out of 5 average rating, 52 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

A spacious screened-in patio presents a serene view of the waterfront. Comfortable seating arrangements are complemented by a dining table, while natural light illuminates the terracotta floor. The outdoor scenery features lush greenery and a distant dock, enhancing the tranquil atmosphere.

4.91 out of 5 average rating, 11 reviews

Jet Ski Adventure - Family Getaway

An airy open-concept living area features a modern kitchen with sleek cabinetry and a spacious island. Floor-to-ceiling sliding glass doors frame panoramic ocean views and allow natural light to fill the room, while comfortable seating provides a cozy space to relax.

5.0 out of 5 average rating, 61 reviews

Luxurious Beachfront Suite

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.

4.95 out of 5 average rating, 82 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

The exterior of the home features a well-maintained front yard, lush with grass and mature trees providing shade. A paved driveway leads to a two-car garage, bordered by a fenced-in area that ensures privacy.

4.94 out of 5 average rating, 54 reviews

Boat House | Boat Ramp, Grill, 1mile to Beach!

The exterior of a multi-level property features a private swimming pool surrounded by lounge chairs. Large windows reflect natural light, while a rooftop deck is visible above. The home is set against a backdrop of sandy terrain and distant buildings, emphasizing its spacious design.

4.95 out of 5 average rating, 58 reviews

NEW•Sleep16•HeatedPool•Destin Beach•Rooftop Views!

A spacious contemporary property is set against a backdrop of coastal scenery. The exterior features a bright façade with multiple balconies. A private pool is visible beside well-manicured lawns, surrounded by pathways leading to the ocean view in the distance.

5.0 out of 5 average rating, 17 reviews

62 Blue View Lakefront Private Pool 5 Min to Beach