Book Holiday Homes in Santa Rosa Island

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Featured Holiday Homes in Santa Rosa Island

5 bed/3 Bath sleeps 19 Guests! Private Pool and steps to the Gulf!

5 bed/3 Bath sleeps 19 Guests! Private Pool and steps to the Gulf!

Pensacola Beach
With a stay at this vacation home in Pensacola Beach (Toilla Segunda), you'll be a 5-minute walk from Pensacola Beach Beaches and 5 minutes by foot from Opal ...
5 bed/3 Bath sleeps 19 Guests! Private Pool and steps to the Gulf!
Beachside Haven: Spacious 6-Bedroom Retreat Just Steps from the Sand

Beachside Haven: Spacious 6-Bedroom Retreat Just Steps from the Sand

Pensacola Beach
With a stay at this vacation home in Pensacola Beach (Villa Primera), you'll be steps from Pensacola Beach Beaches and 15 minutes by foot from Pensacola Beach ...
Beachside Haven: Spacious 6-Bedroom Retreat Just Steps from the Sand
Beautiful Cozy Beach Cottage, 1 block to beach, west of hotels, easy access

Beautiful Cozy Beach Cottage, 1 block to beach, west of hotels, easy access

Pensacola
With a stay at this vacation home in Pensacola Beach (Toilla Segunda), you'll be steps from Pensacola Beach Beaches and 15 minutes by foot from Opal Beach.
Beautiful Cozy Beach Cottage, 1 block to beach, west of hotels, easy access
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2 bedroom, walk to the Beach! Sleeps 6, outdoor games and yard space!

2 bedroom, walk to the Beach! Sleeps 6, outdoor games and yard space!

Fort Walton Beach
With a stay at this vacation home, you'll be centrally located in Fort Walton Beach, within a 5-minute walk of Fort Walton Beaches and Okaloosa Island ...
2 bedroom, walk to the Beach! Sleeps 6, outdoor games and yard space!
The Palms by Scenic Stays-Beautiful home residing in the heart of Navarre FL

The Palms by Scenic Stays-Beautiful home residing in the heart of Navarre FL

Navarre
When you stay at this vacation home in Navarre, you'll be on the beach, a 1-minute drive from Navarre Beach and 5 minutes from Opal Beach.
The Palms by Scenic Stays-Beautiful home residing in the heart of Navarre FL
Southern Breeze 4 - Gulf Front Townhome

Southern Breeze 4 - Gulf Front Townhome

Navarre
With a stay at Southern Breeze 4 - Gulf Front Townhome in Navarre, you'll be on the beach, a 4-minute walk from Navarre Beach and a 4-minute drive from Opal ...
Southern Breeze 4 - Gulf Front Townhome
Emerald Shores: Steps from the Gulf, Navarre Beach

Emerald Shores: Steps from the Gulf, Navarre Beach

Navarre
With a stay at this vacation home in Navarre (Sugar Beach), you'll be a 1-minute drive from Navarre Beach and 6 minutes from Opal Beach.
Emerald Shores: Steps from the Gulf, Navarre Beach
6 bedroom 5 bathroom Home with Private Pool

6 bedroom 5 bathroom Home with Private Pool

Pensacola Beach
Located in Pensacola Beach (Toilla Segunda), this vacation home is steps from Pensacola Beach Beaches and a 2-minute drive from Opal Beach.
6 bedroom 5 bathroom Home with Private Pool
Ultimate Family Home!   Game Porch / No Stairs / Pets / Pool / Tesla Charger

Ultimate Family Home! Game Porch / No Stairs / Pets / Pool / Tesla Charger

Pensacola Beach
With a stay at this vacation home in Pensacola Beach (Villa Segunda), you'll be within a 5-minute walk of Pensacola Beach Beaches and Opal Beach.
Ultimate Family Home! Game Porch / No Stairs / Pets / Pool / Tesla Charger
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Santa Rosa Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Santa Rosa Island vacation homes are the perfect way for you to wing it.

Holiday houses in Santa Rosa Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Santa Rosa Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Santa Rosa Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Santa Rosa Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Santa Rosa Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Santa Rosa Island Holiday Homes essential information

Accommodation
519 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
5 bed/3 Bath sleeps 19 Guests! Private Pool and steps to the Gulf!, Beachside Haven: Spacious 6-Bedroom Retreat Just Steps from the Sand, Beautiful Cozy Beach Cottage, 1 block to beach, west of hotels, easy access, 2 bedroom, walk to the Beach! Sleeps 6, outdoor games and yard space!, The Palms by Scenic Stays-Beautiful home residing in the heart of Navarre FL, Southern Breeze 4 - Gulf Front Townhome, Emerald Shores: Steps from the Gulf, Navarre Beach, 6 bedroom 5 bathroom Home with Private Pool, Ultimate Family Home! Game Porch / No Stairs / Pets / Pool / Tesla Charger

Top trending hotels in Santa Rosa Island

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Miracle Strip Parkway Southeast, 1500, Fort Walton Beach, FL
Fully refundableReserve now, pay when you stay
With a stay at The Island Resort at Fort Walton Beach in Fort Walton Beach, you'll be on the beach, a 4-minute walk from Boardwalk on Okaloosa Island and 7 minutes ...
The Island Resort at Fort Walton Beach
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd, Fort Walton Beach, FL
Fully refundableReserve now, pay when you stay
When you stay at Wyndham Garden Fort Walton Beach Destin in Fort Walton Beach, you'll be on the beach, within a 5-minute walk of Fort Walton Beaches and Okaloosa ...
Wyndham Garden Fort Walton Beach Destin
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road, Pensacola Beach, FL
Fully refundableReserve now, pay when you stay
With a stay at Surf & Sand Hotel in Pensacola Beach, you'll be 0.5 mi (0.8 km) from Pensacola Beach Gulf Pier and 6.7 mi (10.7 km) from Fort Pickens.
Surf & Sand Hotel
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Hampton Inn Pensacola Beach

Hampton Inn Pensacola Beach

2.5 out of 5
2 Via De Luna Drive, Pensacola Beach, FL
Fully refundableReserve now, pay when you stay
With a stay at Hampton Inn Pensacola Beach in Pensacola Beach (Plaza Primera), you'll be steps from Pensacola Beach Boardwalk and 3 minutes by foot from Pensacola ...
Hampton Inn Pensacola Beach
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.