Holiday houses in Santa Rosa Island

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Top-rated holiday rentals in Santa Rosa Island

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

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Guest favourite

Condo in Navarre

4.9 out of 5 average rating, 143 reviews

Steps to the Beach / Sleeps 4 w/ King BR & 2 BA

Renter must be 25 years or older & residing in the unit for the entire length of the reservation. Add'l guest of all ages welcome. No local rentals (<75 miles) 1st Floor/ King & twin bunks / Sleeps 4 Main bedroom w/ensuite bath/Full bath in hall Crib available w/request 2 Wall mounted TVs Fully equipped kitchen & washer/dryer Towels & sheeted beds. 4 beach towels & cooler Steps from the Santa Rosa Sound & Gulf/affordable vacation w/ pool (not heated), gas grills, outdoor dining & parking.

8 – 15 Nov

$1,358 AUD total

Guest favourite

Apartment in Gulf Breeze

4.96 out of 5 average rating, 142 reviews

Redfish Loft, private waterfront Apt. on East Bay

Light airy open floor plan " pet friendly " loft style apartment with private bedroom. Watch the blue herons & dolphins, sit on one of two private decks sipping coffee as you watch the sunrise on the Bay. Paddle the clear waters in our kayaks or bring your SUP. Cook your fresh catch on your private grill or visit a local seafood restaurant. Private, secluded, quiet neighborhood. Join us @ Fire pit that is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

23 – 30 Dec

$1,869 AUD total

Guest favourite

Guest suite in Gulf Breeze

4.9 out of 5 average rating, 143 reviews

East Bay Getaway

Welcome to East Bay Getaway, a private studio with modern conveniences you expect. This clean and comfortable room with private entry is attached to a home on more than an acre. It features a kitchenette, high-speed WiFi and a 32" Smart TV . Dedicated HVAC system. Plenty of outdoor space to enjoy and a bike/walk path is directly across the street. Ample parking for larger vehicles/boats. About a 20 min drive to Navarre Beach and Pensacola beach, with places to eat and shop only a few minutes.

28 Oct – 4 Nov

$1,093 AUD total

Guest favourite

Condo in Pensacola Beach

4.96 out of 5 average rating, 160 reviews

Gorgeous condo steps from beach!

“Welcome to Island Time” Escape to Pensacola Beach!! Beautiful renovated one bedroom condo w/ sleeper sofa on Sabine Bay. You are just across the street from Pensacola Beaches beautiful white sand and blue waters. Walking distance to restaurants & activities. Pensacola Beach is the ideal destination if you are looking for a wide variety of activities. Soak in the sun-drenched days while you enjoy your vacation the way it is supposed to be. Blue Angels wk. is open. Requires 7/9 to 7/14 stay.

26 Nov – 3 Dec

$1,889 AUD total

Guest favourite

Guesthouse in Milton

4.99 out of 5 average rating, 112 reviews

Charming Bayou Bungalow - walk to downtown Milton!

Enjoy visiting historic Milton while staying in our comfortable cottage, which is close to everything making it easy to plan your visit. Walk to downtown Milton for live music, festivals, breweries, restaurants. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop New Queen bed with comfy Serta mattress.

11 – 18 Jan

$1,279 AUD total

Guest favourite

Condo in Navarre

4.97 out of 5 average rating, 102 reviews

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, lighted, private fishing pier, where no fishing license is required.

22 Feb – 1 Mar

$1,704 AUD total

Guest favourite

Guesthouse in Navarre

4.97 out of 5 average rating, 355 reviews

Southern Wind Guest Cottage

Private guest cottage 100 feet from main house. Very quiet; parking 5 steps to entrance. Queen-size bed with mattress topper, sleeps 2. Full bathroom. Full refrigerator with ice maker, microwave, coffee maker, dining table with 2 chairs, new large screen TV receives 300 channels, WiFi, and Netflix. Heating and Air Conditioning controlled by guests. Keyless entry. Excellent location minutes from beach, 5 minutes from Wal-Mart Supercenter, and a few minutes from restaurants.

3 – 10 Mar

$1,075 AUD total

Guest favourite

Cottage in Pensacola

4.99 out of 5 average rating, 406 reviews

Pensacola Pelican Retreat

Beautifully remodeled and updated in the summer of 2017, this vintage 1943, one bedroom, one bath, full kitchen cottage home is located in classic East Pensacola Heights. This 570 sq foot home is located in a safe, family oriented, quiet neighborhood. Its palm tree shaded yard with large deck, gas grill, seating and hammock is conveniently located only minutes to interstate 10, Pensacola's Airport, downtown and beautiful, sugar white beaches and turquoise water.

8 – 15 Dec

$1,439 AUD total

Superhost

Home in Milton

4.79 out of 5 average rating, 151 reviews

*Waterfront Home w/Boat Dock, & Kayaks!

Read full description before booking! 25-30 minutes to the beach depending on traffic. Bring your boat and dock it in your back yard!! Sit on the porch and enjoy coffee in the morning listening to the birds and frogs nearby. The home is nestled in the quiet community of Escambia Shores. Surrounded by tall pines this relaxing home is perfect for a family vacation or honeymoon. Great fishing in the canal or off the dock! Or Kayak into the bay to fish!

14 – 21 Oct

$1,334 AUD total

Guest favourite

Cottage in Pensacola

4.99 out of 5 average rating, 142 reviews

Beach Vibes on Downtown’s Side

This eco-friendly cottage hosts a peaceful Gulf Coast theme on a quiet street, just blocks away from all the action. Located on the edge of downtown, you're never too far away from all Pensacola has to offer, and a quick jaunt to Pensacola or Perdido Beach. This home offers Excellent access to Wahoos Stadium, Sanders Beach, The Oar House, Pensacola Yacht Club, Pensacola Country Club, Joe Patti's, and Pensacola's Naval Air Station.

16 – 23 Aug

$1,407 AUD total

Guest favourite

Home in Gulf Breeze

4.88 out of 5 average rating, 173 reviews

Heart of Gulf Breeze only minutes to Pcola beach!

Your family will be close to everything when you stay at this centrally-located home. Private unit in a duplex located about 15 minutes to Pensacola beach, and 20 minutes to Navarre beach! Large fenced in back yard with table and chairs on patio. Wifi is available along with fire sticks to watch movies and TV shows. Full kitchen and coffee maker at your disposal!

27 Sept – 4 Oct

$1,212 AUD total

Guest favourite

Condo in Navarre

4.92 out of 5 average rating, 414 reviews

"Anchors Away" - Studio Condo w/ easy beach access

Well located studio apartment with full kitchen and bath. Awesome waterfront view, cozy dining and living space. Across the street from the beautiful white sands of Florida’s “Best Kept Secret” Navarre Beach. There is an Instagram: @anchorsawaynavarre with the best local restaurants and things to do while staying in Paradise.

2 – 9 Dec

$1,697 AUD total