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Vacation rentals in Santa Rosa Island, Florida

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Top-rated vacation rentals in Santa Rosa Island, Florida

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Guest favorite
Condo in Pensacola Beach

La Playa Esmeralda-Panoramic Sunset Views

Welcome to La Playa Esmeralda, a beautifully renovated 2nd floor studio. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 2 comfortable beds-1 regular and 1 Murphy bed, along with a coffee bar and fully equipped kitchen. You're just a 5 minute walk to the beach. Enjoy a dip in the pool, grilling in the gazebo and fish all night long on our large, private fishing pier, no fishing license required. Early check-in avail.

4.94 out of 5 average rating, 204 reviews
Top guest favorite
The outdoor pool is framed by a screened enclosure, providing clear views of the tranquil bay waters. Comfortable lounge chairs are positioned beside the pool, and potted plants add a touch of greenery. A wooden dock extends into the bay, enhancing the serene ambiance.
Home in Navarre

East Bay Hideaway — A Private Waterfront Escape

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

4.97 out of 5 average rating, 196 reviews
Top guest favorite
The exterior of a newly renovated beach home is showcased, featuring a large covered front porch with white railings. The landscape includes a gravel driveway bordered by greenery, and a tree provides shade. The house is painted in calming blue hues against a clear sky.
Home in Navarre

Beautiful spacious* 5 min Walk to Bay* EV charger*

Luxurious Beach Home is newly renovated, located in the heart of Navarre. Surrounded by grocery, shopping, attractions, and many great dining options. The bay is a 5 minute walk and it's a five minute drive to the Navarre Bridge where our sugar white sand beaches and beautiful water views for miles await you. This 3 BR each with a TV and 3.5 bathroom home features plenty of space for a family or couples to spread out, including a large back deck with grill and huge covered front porch.

4.95 out of 5 average rating, 166 reviews
Top guest favorite
Home in Pensacola Beach

Kokomo Key - 2 minutes to Beach - Private Pool

If you've been searching for Kokomo Key... Here it is—your tropical escape to the islands. White sand, turquoise waters… it’s got all the vibes of a place where time slows down and the only agenda is relaxation. Relax with the whole family at this peaceful beach house with a private pool, hammocks, unobstructed views of Santa Rosa Sound, and a 2-minute walk to the stunning Gulf beaches! We are pet-friendly, but please remember to let us know you are bringing your pets by checking the box!

4.97 out of 5 average rating, 138 reviews
Guest favorite
A bright living area features light blue sofas complemented by patterned cushions. A wooden coffee table sits in the center, topped with a decorative tray. A ceiling fan hangs above, and a large framed artwork depicting a beach scene is mounted on the wall.
Home in Navarre

Perfect Private Navarre Beach Getaway Near Destin!

Hello! 3 Bedroom 2 Bath Spacious Lux home right across the street from Navarre Beach. There is also a Queen size sleeper couch in the back room. Games for families and a projector screen to enjoy a movie night. Fully enclosed backyard with a Pergola and bar area, lase cornhole, speakers, firepit and grill. Whether you're at the beach or the house, you will have a great stay! Walking distance to many places! We can't wait to host you and your family! Please reach out with any questions.

4.92 out of 5 average rating, 117 reviews
Top guest favorite
The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.
Home in Milton

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

4.96 out of 5 average rating, 268 reviews
Top guest favorite
A single-story house is set in a lush yard featuring green grass and mature trees. The driveway leads to a two-car garage, with a circular flower bed showcasing a small palm plant in the foreground. Clear blue skies serve as a backdrop.
Home in Navarre

Starfish Beach House - Great Getaway

Welcome to the Starfish Beach House. Our home is a quiet retreat just one mile from Navarre Beach, voted one of Florida's top 10 beaches. You will have the run of this three bedroom two bathroom home which features a king size bed, a queen sized bed and two twin beds and tons of amenities. The home is also equal distance to Destin or Pensacola so you will enjoy easy access to a wide selection of what the Gulf Coast has to offer. ***Six Guests Maximum!***

4.96 out of 5 average rating, 152 reviews
Top guest favorite
A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.
Home in Pensacola Beach

Soundside Paradise

Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

4.98 out of 5 average rating, 168 reviews
Top guest favorite
Home in Navarre

Private Heated Pool, 10 Min to Navarre Beach

Escape to Your Private Heated Pool Oasis – 10 Min to Navarre Beach Relax in this spacious 3-bedroom home featuring a private screened-in heated pool (Mar 1–Dec 31) and fully fenced backyard. Located just a 10-minute drive to Navarre Beach in a quiet residential neighborhood, this home is perfect for families and groups (sleeps up to 11). Walk 3–4 minutes to Santa Rosa Sound, or drive to the white sands of Navarre Beach for the full Gulf experience.

4.91 out of 5 average rating, 135 reviews
Top guest favorite
The cabin is nestled among shady oak trees, featuring a wooden deck with seating and a hammock for relaxation. A charcoal grill is positioned nearby, and the surrounding area showcases a dirt path leading to a natural, serene environment.
Cabin in Gulf Breeze

Waterfront tiny Cabin/ Glamping

Quaint waterfront cabin! Peaceful surroundings, shady oak trees, hammock, boat launch, beautiful dock for enjoying the sunrise. Cabin has a loft with Japanese bed, Murphy bed, and futon. Bathroom has a toilet and shower. simple kitchenette with toaster oven, burner, sink, microwave, full fridge, and dishes. Television has DVD player no cable!, no WiFi!. Small dinette table w/4 chairs. A/C; NO PARITIES ALLOWED! Sleeps 4 comfortably

4.91 out of 5 average rating, 579 reviews
Top guest favorite
A spacious balcony provides views of the ocean and shoreline, with several outdoor seating options including two chairs and a table. The adjacent pool area is visible below, framed by the building's clean lines and expansive glass doors leading into the living space.
Apartment in Pensacola Beach

Wake Up to Waves Crashing! ~Beachfront Condo~

Be our guest in our 2 Bed/2 Bath condo located in Emerald Surf on beautiful Navarre Beach. Enjoy a Gulfside pool and boardwalk for private beach access. Each bedroom has a 32" TV and the living room has a 65” TV although we are sure you'll be too busy enjoying the amazing ocean views from the living room and balcony! Our unit is located on the 3rd floor which can be accessed by elevator or stairs. .

4.95 out of 5 average rating, 111 reviews
Top guest favorite
A classic waterfront home is shown from the outside, featuring a large front porch with white railings. Colorful kayaks and paddleboards are displayed on a wooden rack beside a grassy yard, surrounded by lush greenery. Ceiling fans hang above, providing comfort.
Home in Fort Walton Beach

3 Br Waterfront Florida Classic on the Bayou

Enjoy the comfort and beauty of classic old Florida at this beautiful waterfront home. Moments away from white sand beaches and downtown, you are in an oasis of relaxation here at the Florida Classic on the Bayou. This home was thoughtfully designed and cherished by a prominent local family and features rich Florida history and details. It is our pleasure to share this oasis with you.

4.96 out of 5 average rating, 113 reviews

Popular amenities for Santa Rosa Island vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Santa Rosa Island house rentals

Guest favorite
A covered deck is featured, showcasing a hammock and seating area. Potted plants line the wooden pathway, while large windows provide natural light to the interior. The surrounding greenery adds to the peaceful ambiance of the space.
Home in Navarre

Retreat (access to bayfront property & kayaks)

4.81 out of 5 average rating, 159 reviews
Top guest favorite
A private backyard features a heated pool surrounded by landscaped areas with palm trees and flowers. A covered porch provides shaded seating options, while lounge chairs invite relaxation by the water. A securely fenced area enhances safety and privacy.
Home in Navarre

Good times & tan lines! Only 5 miles to the beach!

4.93 out of 5 average rating, 241 reviews
Top guest favorite
A single-story beach home features a light blue exterior with a welcoming porch. The front yard is landscaped with low-maintenance plants and a driveway leading to a two-car garage. In the background, neighboring homes can be seen among the grassy area.
Home in Navarre

Gorgeous Navarre Home 3 Bd2 Bth

4.97 out of 5 average rating, 295 reviews
Top guest favorite
A two-story beach house is showcased with a welcoming entrance featuring white steps leading to a covered porch adorned with flowing curtains. Palm trees and lush greenery frame the property, while a garage is visible underneath the home.
Home in Pensacola Beach

The Purple Sunset-200ft to Beach w Pool

4.96 out of 5 average rating, 164 reviews
Superhost
A private pool is surrounded by a spacious patio, featuring palm trees and lush landscaping. The pool's clear water reflects the sky, while a nearby canal offers a serene view with docked boats in the distance.
Home in Pensacola Beach

Beachie-Private Pool!

4.84 out of 5 average rating, 122 reviews
Top guest favorite
A custom upright piano converted into a bar is displayed, featuring blue lighting and an array of glassware. A colorful art piece hangs above the piano, alongside a unique lamp atop a wine barrel. The modern decor enhances the inviting atmosphere.
Home in Navarre

1.5 mi to Beach-New Pool! Smart home-Modern Decor!

5.0 out of 5 average rating, 135 reviews
Guest favorite
The living room features two comfortable leather sofas positioned around a central coffee table. A large wall-mounted television displays a cozy bookshelf scene. A neutral-toned area rug covers the floor, and a floor lamp provides soft lighting. Decorative items add a homey touch.
Home in Gulf Breeze

Great Gulf Breeze Getaway Near Pensacola Beach

4.88 out of 5 average rating, 152 reviews
Top guest favorite
The exterior of the three-story beach home is showcased, featuring a large, inviting pool surrounded by lounge chairs. A spacious deck is visible, with the front of the house displaying double gables and multiple balconies. Lush landscaping is present around the pool area.
Home in Pensacola Beach

Private Pool, Steps to the beach, Golf cart

4.97 out of 5 average rating, 34 reviews

Other great vacation rentals in Santa Rosa Island, Florida

Guest favorite
A rustic patio space is designed with wooden walls and a comfortable seating area, featuring a chair and a loveseat. A hanging plant adds greenery, while stone-paved paths and decorative plants enhance the natural setting. Sunlight filters through the trees, creating a warm ambiance.
Tiny home in Gulf Breeze

The Backyard Cottage

4.9 out of 5 average rating, 122 reviews
Top guest favorite
A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.
Condo in Pensacola Beach

Beachfront Condo • Pool & Resort Perks

4.99 out of 5 average rating, 156 reviews
Top guest favorite
A private balcony is featured with two woven chairs and a wooden table, overlooking expansive views of the Gulf waters. The open glass doors allow natural light to fill the space, highlighting the coastal ambiance and serene colors of the sea and sky.
Condo in Pensacola Beach

Tide Together on the Gulf at Beach Colony East

5.0 out of 5 average rating, 40 reviews
Top guest favorite
Home in Pensacola Beach

The Surf Club at Navarre Beach

5.0 out of 5 average rating, 48 reviews
Guest favorite
A row of newly constructed townhomes is presented, featuring a light blue exterior and symmetrical design. Each unit has a garage with a modern door. A spacious driveway is paved with concrete and bordered by small white stones, enhancing the clean and organized appearance.
Home in Gulf Breeze

E-Sea Breeze

4.96 out of 5 average rating, 67 reviews
Guest favorite
An aerial view captures the arrangement of buildings surrounding a central pool area, with clear views of nearby high-rises and the beachfront. The vibrant turquoise waters of the Gulf contrast with sandy beaches, illustrating the proximity to beautiful coastal scenery.
Home in Pensacola Beach

Spacious 4BR Coastal Home | Steps from Beach

4.92 out of 5 average rating, 38 reviews
Top guest favorite
Home in Gulf Breeze

Coastal Family Retreat | Pool, Fire Pit & Playset

5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Navarre

Navarre Peaceful Oasis

4.98 out of 5 average rating, 44 reviews

Destinations to explore