A sandy beach path with wooden fences and tall grasses.

Santa Rosa Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Santa Rosa Island vacation rentals

1. 13th Floor OceanFront,Free Beach Chairs & Unbrella Service HeatedPool ArcadeGame

13th Floor OceanFront,Free Beach Chairs & Unbrella Service HeatedPool ArcadeGame
Navarre
10.0 out of 10, Exceptional, (39 reviews)
"Great trip!!!"
United States
Aimie B.
The price is CA $127
CA $425 total
includes taxes & fees
Oct 17 - Oct 18
13th Floor OceanFront,Free Beach Chairs & Unbrella Service HeatedPool ArcadeGame

2. Mermaid Hideaway at El Matador Unit 621!

Mermaid Hideaway at El Matador Unit 621!
Okaloosa Island
10.0 out of 10, Exceptional, (72 reviews)
"Great place to stay. The host was awesome! Very quiet and a nice short walk right beach! Definitely will be back again!!"
United States
Brent M.
Mermaid Hideaway at El Matador Unit 621!

3. Okaloosa Island. Great Location. 3 Min Walk to Beach. 6 Mile drive to Destin.

Okaloosa Island. Great Location. 3 Min Walk to Beach. 6 Mile drive to Destin.
Okaloosa Island
9.8 out of 10, Exceptional, (185 reviews)
"Wonderful place in a great location. Super easy check in and very clean."
United States
Jaime
The price is CA $106
CA $405 total
includes taxes & fees
Oct 11 - Oct 12
Okaloosa Island. Great Location. 3 Min Walk to Beach. 6 Mile drive to Destin.

4. Nautilus 2410 Gulf View 2BD/2BA 4th Floor. Free Beach Service 3/1-10/31

Nautilus 2410 Gulf View 2BD/2BA 4th Floor. Free Beach Service 3/1-10/31
Okaloosa Island
9.4 out of 10, Exceptional, (52 reviews)
"Nice Condo!!"
United States
Jodie W.
The price is CA $220
CA $706 total
includes taxes & fees
Oct 8 - Oct 9
Nautilus 2410 Gulf View 2BD/2BA 4th Floor. Free Beach Service 3/1-10/31

5. Okaloosa Island 1BR Condo by White Sand Beach

Okaloosa Island 1BR Condo by White Sand Beach
Okaloosa Island
9.6 out of 10, Exceptional, (26 reviews)
"For the price and location I think this is a great place to stay!! "
United States
Sara B.
The price is CA $89
CA $396 total
includes taxes & fees
Oct 26 - Oct 27
Okaloosa Island 1BR Condo by White Sand Beach

6. Unit #3 Waterfront + Heated Pool and Spa Access

Unit #3 Waterfront + Heated Pool and Spa Access
Okaloosa Island
9.6 out of 10, Exceptional, (7 reviews)
"It was amazing! The hosts were super helpful and friendly"
United States
Sam M.
The price is CA $161
CA $369 total
includes taxes & fees
Sep 27 - Sep 28
Unit #3 Waterfront + Heated Pool and Spa Access

7. Updated Gulf-Side Studio at Destin West with Free Beach Service for 2

Updated Gulf-Side Studio at Destin West with Free Beach Service for 2
Okaloosa Island
8.4 out of 10, Very good, (5 reviews)
"My husband and I stayed here and it was wonderful! We will be coming back! We came alone but next time we will bring the kids."
United States
Jillian B.
The price is CA $163
CA $518 total
includes taxes & fees
Sep 26 - Sep 27
Updated Gulf-Side Studio at Destin West with Free Beach Service for 2

8. 2 Bedroom Condo on the Beach at Okaloosa Island

2 Bedroom Condo on the Beach at Okaloosa Island
Okaloosa Island
9.8 out of 10, Exceptional, (36 reviews)
"Great view of the ocean…easy walk to the beach. Comfortable beds in both rooms and a spacious well-equipped kitchen. "
United States
Gabi I.
The price is CA $144
CA $572 total
includes taxes & fees
Oct 3 - Oct 4
2 Bedroom Condo on the Beach at Okaloosa Island

9. Okaloosa Island Castaway-Pets Allowed

Okaloosa Island Castaway-Pets Allowed
Okaloosa Island
9.0 out of 10, Wonderful, (17 reviews)
"Had a great time and was key location to beach, restaurants, and activities "
United States
Michael W.
The price is CA $107
CA $347 total
includes taxes & fees
Sep 30 - Oct 1
Okaloosa Island Castaway-Pets Allowed

10. Second-floor, airy condo with great views - close to dining & shopping

Second-floor, airy condo with great views - close to dining & shopping
Okaloosa Island
8.8 out of 10, Excellent, (29 reviews)
"we like this place, Thanks"
United States
Huonggiang N.
The price is CA $205
CA $482 total
includes taxes & fees
Oct 25 - Oct 26
Second-floor, airy condo with great views - close to dining & shopping

11. Seacrest 305 is a 2 BR Gulf front on Okaloosa Island, Sleeps 6

Seacrest 305 is a 2 BR Gulf front on Okaloosa Island, Sleeps 6
Okaloosa Island
10.0 out of 10, Exceptional, (3 reviews)
"Great location, and great condo with plenty of room for our family. I would definitely recommend. "
United States
Tommy
The price is CA $234
CA $667 total
includes taxes & fees
Oct 1 - Oct 2
Seacrest 305 is a 2 BR Gulf front on Okaloosa Island, Sleeps 6

12. Destin West Bayside Pelican 608 - Gorgeous bayside condo with lazy river and beach access

Destin West Bayside Pelican 608 - Gorgeous bayside condo with lazy river and beach access
Okaloosa Island
9.2 out of 10, Wonderful, (15 reviews)
"Enjoyed our stay! "
United States
Christel W.
The price is CA $205
CA $554 total
includes taxes & fees
Sep 29 - Sep 30
Destin West Bayside Pelican 608 - Gorgeous bayside condo with lazy river and beach access

13. Beautifully Remodeled Bay Front Condo

Beautifully Remodeled Bay Front Condo
Navarre
10.0 out of 10, Exceptional, (86 reviews)
"A great, efficient, clean place for our family of 4. Would highly recommend."
United States
Family S.
The price is CA $191
CA $420 total
includes taxes & fees
Sep 30 - Oct 1
Beautifully Remodeled Bay Front Condo

14. Kid-friendly! Lazy River~Skywalk over to beach!

Kid-friendly! Lazy River~Skywalk over to beach!
Okaloosa Island
9.4 out of 10, Exceptional, (36 reviews)
"Great property, spa"
United States
Grant A.
The price is CA $205
CA $608 total
includes taxes & fees
Sep 28 - Sep 29
Kid-friendly! Lazy River~Skywalk over to beach!

15. Sunny Happy Place by the Beach, Sleeps 6. Beach service March 1 to October 30.

Sunny Happy Place by the Beach, Sleeps 6. Beach service March 1 to October 30.
Okaloosa Island
9.6 out of 10, Exceptional, (30 reviews)
"Very close to the beach and a lot of other things close by, walking distance for majority of necessities."
United States
Hunter
The price is CA $264
CA $561 total
includes taxes & fees
Oct 8 - Oct 9
Sunny Happy Place by the Beach, Sleeps 6. Beach service March 1 to October 30.

16. V310 Cozy Gulf View Villa w/Private Balcony Washer/Dryer & Free Beach Chairs

V310 Cozy Gulf View Villa w/Private Balcony Washer/Dryer & Free Beach Chairs
Okaloosa Island
8.4 out of 10, Very good, (42 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was nice! I was sick the hole time I was there but I still enjoyed it!"
United States
Mike S.
The price is CA $167
CA $504 total
includes taxes & fees
Sep 27 - Sep 28
V310 Cozy Gulf View Villa w/Private Balcony Washer/Dryer & Free Beach Chairs

17. Summerwinds 403E Beachfront Vacation and ask about November Monthly Special

Summerwinds 403E Beachfront Vacation and ask about November Monthly Special
Navarre
9.8 out of 10, Exceptional, (112 reviews)
"Beautiful room with an awesome view."
United States
Lee H.
The price is CA $140
CA $657 total
includes taxes & fees
Sep 28 - Sep 29
Summerwinds 403E Beachfront Vacation and ask about November Monthly Special

18. V505 Beachside Villa Stunning Gulf & Bay Views Steps from Sugar-White Sands!

V505 Beachside Villa Stunning Gulf & Bay Views Steps from Sugar-White Sands!
Okaloosa Island
8.6 out of 10, Excellent, (37 reviews)
"Convenient and clean."
United States
christi c.
The price is CA $170
CA $508 total
includes taxes & fees
Sep 27 - Sep 28
V505 Beachside Villa Stunning Gulf & Bay Views Steps from Sugar-White Sands!

19. BeachFRONT!! 65" HD TV, WIFI, Netflix, and View!

BeachFRONT!! 65" HD TV, WIFI, Netflix, and View!
Okaloosa Island
9.8 out of 10, Exceptional, (113 reviews)
"Just as advertised! Awesome view and easy access to a pool and beautiful quiet beach just downstairs. We had an amazing time and would stay here again in a heartbeat."
United States
David P.
The price is CA $204
CA $485 total
includes taxes & fees
Sep 29 - Sep 30
BeachFRONT!! 65" HD TV, WIFI, Netflix, and View!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Santa Rosa Island Hotel Reviews

Find out more about Santa Rosa Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Santa Rosa Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia