
Vacation rentals in Santa Rosa Island
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Top-rated vacation rentals in Santa Rosa Island
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Popular amenities for Okaloosa Island vacation rentals
Okaloosa Island house rentals

Destin Retreat: Oceanview Poolside Luxury Condo

Walk/Free Shuttle to Beach, Resort Pool, Huge Home

Private home close to military bases and beaches

FWB Vacation House-TV in rooms Free Wi-Fi & Grill

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Vet-Owned 3BR Home Near Beach & Base|Pet-Friendly!

#1 4BR HUGE PET Friendly Home w/ your own pool!

Cozy Coastal Retreat | Near Destin &Okaloosa Beach
Okaloosa Island beach vacation rentals

Keeler Island Princess Okaloosa Island Beachfront

Beauty & The Beach near Gulf Beaches & Bay

“Sandy Thongs” Beachfront Oasis Amazing Gulf View

Sunshine and beach time /Okaloosa Island

Fall Deals-Direct Beach FRONT-Lazy River-Views!

Destin West Villa #V502 Beach Vacation Awaits

Beachfront! Newly remodeled! Right on the beach!

On the Gulf 2 Bed, 2 Bath Third Floor Condo
Okaloosa Island cottage rentals

Cheeks On The Beach-30% Discount for Fall stays!

Two blocks to the beach! Bikes included!

Gardner's Cottage - Fenced Yard, Bring Your Boat

PaPa Cantina Beach Cottage Old Florida style home

"Quirky Cottage"

One Block to Crystal Beach + Pool + King Bed + Convenient Location

Beach Cottage South of 30a -Steps to Beach & More!

Beachside Bungalow~Location~Steps to Beach & Pool
Quick stats about vacation rentals in Santa Rosa Island
Total rentals
2.7K properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
60K reviews
Family-friendly rentals
2K properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
2.5K properties have a pool
Your guide to Santa Rosa Island
Introduction
If you’re visiting Okaloosa Island, don’t forget to pack a swimsuit. The three-mile-long barrier island, just south of Fort Walton Beach, is between the Choctawhatchee Bay and the Gulf of Mexico on Florida’s Emerald Coast. You practically live at the beach here, spending days pedaling around on a cruiser, stretching out on powder-soft white sands, and sitting down to a seafood dinner fresh from the turquoise gulf waters. But while the beaches here are beautiful — much of the island is protected land — there’s plenty to do besides relax. Kayak or paddleboard on the bay or boat over to Crab Island, a sandbar with a festive atmosphere. Shop and dine on the boardwalk, or visit the area’s theme parks, water parks, and museums. Then cap off the day by enjoying a brilliant sunset on the beach.
The best time to stay in a vacation rental in Santa Rosa Island
It’s almost always beach weather on Okaloosa Island. Summer is hot, humid, and the most popular time to book one of the condos here, with daytime temperatures around 90 degrees Fahrenheit and nights only slightly cooler. But repeat visitors tend to agree that spring and fall are the best times to visit, when the crowds are thinner and temperatures are in the mid-70s and upper 80s — you may even want to pack a light jacket for evenings. Expect an isolated thunderstorm or two, especially during hurricane season, which starts in June and lasts through late October or November. Winter is sunny but cooler, with temperatures in the mid-60s. However, it doesn’t last long, and the 70-degree days usually return in the middle of March.
Top things to do in Santa Rosa Island
Okaloosa Island Pier
Anglers come to the Okaloosa Island Pier, which juts 1,262 feet into the Gulf of Mexico, to sight-cast in the clear waters. There’s gear rental here, and, for a small license fee, you can fish for Spanish mackerel, whiting, tuna, and bluefish. The pier also draws birders and is a lovely place for a stroll or to watch the summer fireworks displays.
The Boardwalk on Okaloosa Island
The oceanfront boardwalk features beach access, picnic pavilions, shops selling beach apparel and water toys, ice cream and candy stores, and several large, open-air seafood shacks and burger bars.
Gulf Island National Seashore
A national treasure, the Gulf Island National Seashore stretches 160 miles from Cat Island, MS, to Okaloosa Island and is split into 12 areas. The final section, just west of the Okaloosa Island hub, is a beautiful small beach on the Choctawhatchee Bay with calm waters that are great for swimming and water sports.
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Okaloosa Island?
Yes! Work meets play with ease at over 1,740 vacation rentals in Okaloosa Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Okaloosa Island?
Experience the best of Okaloosa Island with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Okaloosa Island?
Four-legged friends are welcome in Okaloosa Island. Choose from more than 170 vacation rentals for guests traveling with pets.
Are there Okaloosa Island house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 house rentals with pools in Okaloosa Island, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Okaloosa Island?
Okaloosa Island has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Okaloosa Island have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Okaloosa Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Okaloosa Island have free parking?
Absolutely! We offer over 60 house rentals with free parking in Okaloosa Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Okaloosa Island have a gym?
Absolutely! We offer over 10 house rentals with a gym in Okaloosa Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Okaloosa Island have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Okaloosa Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Okaloosa Island?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with free parking, over 10 homes with a gym, over 20 homes with self check-in, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Rentals with outdoor seating Santa Rosa Island
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- Rentals with an accessible height bed Santa Rosa Island
- Rentals with beach access Santa Rosa Island
- Rentals with a washer and dryer Santa Rosa Island
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- Family-friendly rentals Santa Rosa Island
- Rentals with a patio Santa Rosa Island
- Pet-friendly rentals Santa Rosa Island
- Rentals with pools Santa Rosa Island
- Townhouse rentals Santa Rosa Island
- Condo rentals Santa Rosa Island
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- Waterfront rentals Santa Rosa Island
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- Fitness-friendly rentals Santa Rosa Island
- Beach house rentals Santa Rosa Island
- Villa rentals Santa Rosa Island
- Destin Harbor Boardwalk
- Crab Island
- Princess Beach
- Frank Brown Park
- James Lee Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Gulfarium Marine Adventure Park
- Eglin Beach Park
- Raven Golf Club
- Pensacola Dog Beach West
- Camp Helen State Park
- Fort Walton Beach Golf Course
- Walton Dunes Beach Access
- Wayside Park, Okaloosa Island
- Fred Gannon Rocky Bayou State Park
- Shipwreck Island Waterpark
- Seacrest Beach
- Gulf World Marine Park
- The Track - Destin