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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, 199 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, 193 reviews
Top guest favorite
Apartment in Pensacola Beach

Comfy 1 Bedroom with Pool at Sunset Harbor Condos

Cozy 1 bedroom, 2 bath unit on the 1st floor offers a view of the Santa Rosa Sound from the balcony. Your vacation starts the moment you walk in the door The sugar white sands of the beach and emerald waters of the Gulf are a short walk or 1 minute drive away. The pool is just outside the building near the outdoor grills. The kitchen is well equipped for cooking. The bedroom features a king size bed and TV. The primary bath has a tub/shower combo. You will love this quiet private community.

4.93 out of 5 average rating, 113 reviews
Top guest favorite
A modern kitchen is seen alongside a dining area with a table and stools. The open living space features a sofa and accent chair, with natural light filtering in from a large window. A cozy sleeping area is positioned in the background, adorned with soft decor.
Condo in Pensacola Beach

The Sandy Secret

Welcome to "The Sandy Secret" one of Navarre's Best Kept Secrets. You will love this newly renovated waterfront beauty. Here you will find the best amenities including: gated pool, private beach, gazebo with grills, gated pier, wifi, cable, elevators, and sooooo much more. The Sandy Secret has everything you are looking for in a vacation spot. Comfort, Style, and Priceless Views. Experience Navarre Beach like never before. See why it was voted The Most Relaxing Beach.

4.88 out of 5 average rating, 356 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.

4.95 out of 5 average rating, 264 reviews
Guest favorite
Townhouse in Pensacola Beach

Waterfront Home, Stunning Canal Views, Deck

Canal-front townhome with a private dock and an easygoing layout for coastal living. Enjoy calm water views and relaxed surroundings while staying within walking distance of Navarre Beach. • 3 BR | 2.5 BA | Sleeps 9 • Waterfront deck overlooking canal • About a 9-minute walk to beach • Open living area • Beach gear provided Thoughtfully arranged interiors and welcoming outdoor space make it ideal for a relaxed coastal stay close to both the canal and the Gulf.

4.9 out of 5 average rating, 154 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, 167 reviews
Top 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

Escape to our cozy, one-of-a kind rustic cottage at the Gulf of Mexico! Centrally located, we are just 6 miles from Pensacola Beach, 17 miles from Navarre Beach, and 10 miles from Downtown Pensacola. We offer a quiet, chill environment while being just minutes from shops, restaurants, beaches, nature trails and the zoo. The Backyard Cottage is lovingly placed in our shared yard, so please be respectful of our space that we have chosen to share.

4.9 out of 5 average rating, 119 reviews
Superhost
Home in Navarre

Retreat (access to bayfront property & kayaks)

Our house is your house. A relaxing retreat while vacationing on the Gulf Coast. Minutes from attractions like Navarre beach, this retreat offers a quiet escape away from the hustle and bustle in a family friendly neighborhood. Enjoy your mornings while relaxing on the back deck with your cup of coffee and glass of wine by the fire pit by night. Reach out for discounts on long term offers season stays.

4.81 out of 5 average rating, 156 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, 108 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.

4.95 out of 5 average rating, 111 reviews
Guest favorite
A panoramic view of the Gulf of Mexico stretches across the horizon, showcasing clear blue waters meeting a sandy shoreline. Sunlight glistens on the water, creating a serene atmosphere. A few figures can be seen enjoying the beach, enhancing the tranquil coastal scene.
Condo in Pensacola Beach

Welcome To Florida's Hidden Gem!

Sundunes 184 is a beautiful 8th floor end unit condo. The view from the balcony of the Gulf of Mexico is breathtaking. The owners thought of everything when they remodeled this unit from the updated kitchen, bathrooms, all the furnishing, even brand new TV's. This unit offers one queen bed and one full bed in addition to the sleeper sofa.

4.8 out of 5 average rating, 231 reviews

Popular amenities for Santa Rosa Island vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Santa Rosa Island house rentals

Top guest favorite
Home in Pensacola Beach

Kokomo Key - 2 minutes to Beach - Private Pool

4.97 out of 5 average rating, 135 reviews
Top guest favorite
Bicycles are parked in front of Snow's Surf Shack, showcasing colorful designs. The backdrop features a bright blue building with playful surf-themed artwork. Sunlight bathes the scene, highlighting the inviting atmosphere of this beach getaway.
Home in Navarre

Snow's Surf Shack

4.97 out of 5 average rating, 184 reviews
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*

4.95 out of 5 average rating, 164 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!

4.92 out of 5 average rating, 115 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

4.96 out of 5 average rating, 152 reviews
Top guest favorite
A spacious kitchen area is highlighted by dark wooden cabinetry and stainless steel appliances. The large granite countertop includes seating for four on wooden stools. Soft lighting from pendant fixtures creates a functional workspace, while a window allows natural light to brighten the space.
Home in Navarre

"At Home" near the beach

4.95 out of 5 average rating, 200 reviews
Guest favorite
A welcoming entryway features a decorative round mirror above a console table. A potted plant adds greenery beside the door. A wreath adorns the glass panel of the door, while natural light filters through nearby windows, illuminating the space.
Home in Gulf Breeze

Gulf Breeze getaway w/hot tub, minutes to beach

4.87 out of 5 average rating, 201 reviews
Top guest favorite
A spacious outdoor deck is set with a long table, accommodating multiple guests. Chairs and glassware are arranged neatly for dining. Lush green trees surround the area, offering a relaxed atmosphere, while a glimpse of water can be seen in the distance.
Home in Pensacola

Large Mid-Century Home w/Bay View & Ancient Trees

4.89 out of 5 average rating, 278 reviews

Other great vacation rentals in Santa Rosa Island, Florida

Guest favorite
A spacious living room is furnished with comfortable seating and features large glass doors that open to an ocean view. Soft lighting creates a relaxed environment. Tile flooring complements the coastal decor, and a ceiling fan is visible above.
Townhouse in Pensacola Beach

3-Level Gulf Front Townhome w/ Breathtaking Views

4.83 out of 5 average rating, 100 reviews
Top guest favorite
Townhouse in Pensacola Beach

Palms on the Canal -Kayaks Included! Navarre Beach

4.99 out of 5 average rating, 188 reviews
Top guest favorite
Guesthouse in Pensacola Beach

The Cedarwood 2 @Navarre Beach.

4.98 out of 5 average rating, 158 reviews
Guest favorite
Condo in Pensacola Beach

Pier Bliss

5.0 out of 5 average rating, 8 reviews
Top guest favorite
A private balcony offers sweeping views of the Gulf of Mexico and the long Navarre Beach Pier. The space features outdoor seating, with a lush green accent planter adding a touch of nature to the scene. The tranquil waters and sandy shores are visible beyond.
Condo in Pensacola Beach

Beachfront - Regency | Resort Pool | Sleeps 8

5.0 out of 5 average rating, 70 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
A serene waterfront view showcases a sunset over the water, with warm hues illuminating the sky. Silhouetted dock structures extend into the water, reflecting the vibrant colors. Soft clouds create a peaceful backdrop, enhancing the tranquil atmosphere of the setting.
Condo in Navarre

Waterfront, large balcony. 3 suites king bed

5.0 out of 5 average rating, 63 reviews
Top guest favorite
A spacious living area features a large flat-screen TV mounted above a sleek console, with a comfortable sectional sofa arranged around a round coffee table. Floor-to-ceiling sliding glass doors provide an unobstructed view of the waterfront, allowing natural light to illuminate the room.
Condo in Navarre

Waterfront 3 BDR/3 BA Designer Condo, Private Pier

4.94 out of 5 average rating, 83 reviews

Destinations to explore