Holiday rentals in Santa Rosa Island, Florida

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Top-rated holiday rentals in Santa Rosa Island, Florida

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

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

Guest favourite

Apartment 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 favourite

Home in Navarre

Navarre Vacation Escape

Tucked away in a quiet neighborhood less than 600 feet from Santa Rosa Sound and just minutes from the sugar-white sands of Navarre Beach, this clean, bright 3 bedroom, 3 bath getaway is your new happy place. Come see why Navarre is Florida’s best-kept secret! ✨ UPCOMING FALL HIGHLIGHTS ✨ Sept 12-13: Juana’s Good Time Regatta (Right on Navarre Beach!) Sept 25-27: Annual Pensacola Seafood Festival Oct 3-4: Navarre Fishing Rodeo Oct 11: 33rd Annual Charity Chili Cook-Off & Volleyball Tournament.

5.0 out of 5 average rating, 44 reviews

Top guest favourite

Flat in Pensacola Beach

Blue Heron Retreat w/ 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, 116 reviews

Top guest favourite

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, 167 reviews

Top guest favourite

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.

Apartment in Pensacola Beach

Beachfront Condo • Pool & Resort Perks

Welcome to Pensacola Perch, an 8th‑floor beachfront condo offering expansive views of Pensacola Beach—perfect for dolphin watching and catching the Blue Angels airshow. This modern 2BR/2BA condo sits in the highly sought‑after Emerald Isle gated resort, where guests enjoy premium amenities including direct beach access, two swimming pools, a hot tub, sauna, and a beachfront fitness center. From March–October, enjoy complimentary beach chairs and an umbrella from La Dolce Vita.

4.99 out of 5 average rating, 157 reviews

Top guest favourite

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.

Apartment 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.

4.89 out of 5 average rating, 359 reviews

Top guest favourite

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

Guest favourite

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, 156 reviews

Top guest favourite

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, 169 reviews

Top guest favourite

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 favourite

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.

Flat 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