
Vacation rentals in Santa Rosa Island
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Top-rated vacation rentals in Santa Rosa Island
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Vacation rentals for every style
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Popular amenities for Okaloosa Island vacation rentals
Okaloosa Island beach vacation rentals

Destin West Villa PH01 ~ Penthouse w/ Hot Tub

Retreat by the Sea at Seacrest Condo

Wow! Beachfront 1-min walk to Beach-Aqua Villa 106

"SeaGlass" - Oceanfront with expansive balcony.

Beach Haven l Beautiful Lagoon Pool & Ocean View

One Step to the Beach!

Beachfront Renovated Condo, Spectacular Gulf Views

Sunshine and beach time /Okaloosa Island
Okaloosa Island house rentals

Destin Retreat: Oceanview Poolside Luxury Condo

Private home close to military bases and beaches

Sugar Sand Cottage at Destin Pointe

Up to 40% off! Heated Pool, Pvt Beach, 2 King BR

Magnolia | TVs, Kid Friendly, Grill, & Beach!

Modern 3BR | Central | Vet-Owned | Pets Welcome!

Cap’s Cottage14B • Beachwalk • Pool • Beach Setups

VR, Arcade, Minutes to Everything!
Okaloosa Island cottage rentals

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

Two blocks to the beach! Bikes included!

PaPa Cantina Beach Cottage Old Florida style home

"Quirky Cottage"

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

Charming Beach Cottage- with beach service

It’s Just Darling

Grayton Beach!-Best beach access, bikes, dune lake
Quick stats about vacation rentals in Santa Rosa Island
Total rentals
2.7K properties
Nightly prices starting at
R706 ZAR 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 near Okaloosa Island's top attractions?
You're in luck! Stay at the heart of it all with our vacation rentals near Okaloosa Island's top attractions. We offer over 8,520 vacation rentals near McGuire''s Irish Pub of Destin, over 8,520 vacation rentals near HarborWalk Village, and over 6,890 vacation rentals near Gulfarium Marine Adventure Park, and so much more! Experience the best of Okaloosa Island right on your doorstep.
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.
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!
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 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 30 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.
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- Pet-friendly rentals Santa Rosa Island
- Rentals with a patio Santa Rosa Island
- Family-friendly rentals Santa Rosa Island
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- Beach condo rentals Santa Rosa Island
- Fitness-friendly rentals Santa Rosa Island
- Rentals with pools Santa Rosa Island
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- Rentals with a hot tub Santa Rosa Island
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- Condo rentals Santa Rosa Island
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- Rentals with beach access Santa Rosa Island
- Waterfront rentals Santa Rosa Island
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- Rentals with an accessible height toilet Santa Rosa Island
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- House rentals Santa Rosa Island
- Rentals with a washer and dryer Santa Rosa Island
- Rentals with a sauna Santa Rosa Island
- Rentals with a kayak Santa Rosa Island
- Rentals with outdoor seating Santa Rosa Island
- Destin Harbor Boardwalk
- Crab Island
- Princess Beach
- Frank Brown Park
- James Lee Beach
- Johnson's Beach, Gulf Islands National Seashore
- Navarre Beach Fishing Pier
- Blue Mountain Beach
- Grayton Beach State Park
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Raven Golf Club
- Eglin Beach Park
- Gulfarium Marine Adventure Park
- Fort Walton Beach Golf Course
- Pensacola Dog Beach West
- Walton Dunes Beach Access
- Camp Helen State Park
- Wayside Park, Okaloosa Island
- Fred Gannon Rocky Bayou State Park
- Shipwreck Island Waterpark
- San Carlos Beach
- Gulf World Marine Park
- Eglin Matterhorn Beach Access Point