A sandy beach path with wooden fences and tall grasses.

Santa Rosa Island Holiday Rentals

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Our top choices for Santa Rosa Island holiday rentals

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

2. #204- GULF FRONT, 2ND FLOOR! NOW BOOKING SPRING AND SUMMER! BCH SERVICE INCL.!

#204- GULF FRONT, 2ND FLOOR! NOW BOOKING SPRING AND SUMMER! BCH SERVICE INCL.!
Okaloosa Island
9.8 out of 10, Exceptional, (246 reviews)
"Perfect for a weekend getaway! Very clean and had everything we needed."
United States
Carlissa W.
The price is NZ$817
includes taxes & fees
28 Oct - 29 Oct
#204- GULF FRONT, 2ND FLOOR! NOW BOOKING SPRING AND SUMMER! BCH SERVICE INCL.!

3. 2400 Sq Ft | Sleeps 12 | 700ft Lazy River Retreat

2400 Sq Ft | Sleeps 12 | 700ft Lazy River Retreat
Okaloosa Island
9.8 out of 10, Exceptional, (114 reviews)
"This property was perfect for our crew! It was spacious, beautiful, and very welcoming. The beds were incredibly comfortable, and the decor was thoughtfully done. My favorite part of the property was definitely the balcony area — it was peaceful, relaxing, and absolutely beautiful. We truly enjoyed our stay and will definitely be back!"
United States
Anthony G.
2400 Sq Ft | Sleeps 12 | 700ft Lazy River Retreat

4. Gulf Front 2 bedroom Islander Beach 6007

Gulf Front 2 bedroom Islander Beach 6007
Okaloosa Island
10.0 out of 10, Exceptional, (49 reviews)
"The condo was very welcoming and cozy. Nice beach vibe and great colors. It felt comfortable and we had everything we needed. Great view and huge pool. Nice large balcony to enjoy sunrise and sunset with plenty of seating for family time. We really enjoyed our time here and would definitely look to come back for more memories."
United States
Audrey E.
Gulf Front 2 bedroom Islander Beach 6007

5. Beachfront Escape with Sixth-Floor Views, Free WiFi, Shared Pools, & Gym

Beachfront Escape with Sixth-Floor Views, Free WiFi, Shared Pools, & Gym
Okaloosa Island
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful Condo and Beautiful location. "
United States
Lori S.
The price is NZ$936
includes taxes & fees
2 Oct - 3 Oct
Beachfront Escape with Sixth-Floor Views, Free WiFi, Shared Pools, & Gym

6. Breathtaking views directly facing the Gulf! 3bd/3bath/6

Breathtaking views directly facing the Gulf! 3bd/3bath/6
Okaloosa Island
10.0 out of 10, Exceptional, (104 reviews)
"Property was clean and had a beautiful view! Host was very friendly and responsive"
United States
Dara B.
The price is NZ$877
includes taxes & fees
26 Oct - 27 Oct
Breathtaking views directly facing the Gulf! 3bd/3bath/6

7. Islander Beach Resort/Direct Gulf view from 4th Floor/Sleep 6/No Pets/No Smoking

Islander Beach Resort/Direct Gulf view from 4th Floor/Sleep 6/No Pets/No Smoking
Okaloosa Island
9.8 out of 10, Exceptional, (170 reviews)
"Great view, right on the beach! Perfect for our family of four."
United States
Ashley D.
Islander Beach Resort/Direct Gulf view from 4th Floor/Sleep 6/No Pets/No Smoking

8. Dec-Jan Specials! Summer Place 506- New Paint-Great Location-Spectacular Views!

Dec-Jan Specials! Summer Place 506- New Paint-Great Location-Spectacular Views!
Okaloosa Island
9.4 out of 10, Exceptional, (120 reviews)
"Property was great we had a great time! Property was clean and the views were spectacular"
United States
Joe S.
Dec-Jan Specials! Summer Place 506- New Paint-Great Location-Spectacular Views!

9. 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 NZ$834
includes taxes & fees
18 Oct - 19 Oct
Seacrest 305 is a 2 BR Gulf front on Okaloosa Island, Sleeps 6

10. 4th-floor beach-chic condo at waterscape - waterfall & lazy river

4th-floor beach-chic condo at waterscape - waterfall & lazy river
Okaloosa Island
9.6 out of 10, Exceptional, (15 reviews)
"Enjoyed the location"
United States
Jessie B.
The price is NZ$802
includes taxes & fees
21 Oct - 22 Oct
4th-floor beach-chic condo at waterscape - waterfall & lazy river

11. TURTLE WALK 3 BDR GULF FRONT 2026 Booking up Fast

TURTLE WALK 3 BDR GULF FRONT 2026 Booking up Fast
Okaloosa Island
9.8 out of 10, Exceptional, (45 reviews)
"Great views to wake up to everyday."
United States
Jerald W.
The price is NZ$1,039
includes taxes & fees
27 Oct - 28 Oct
TURTLE WALK 3 BDR GULF FRONT 2026 Booking up Fast

12. ETW 1001: Renovated 1st Floor Convenience with a Perfect Gulf View! 2BR/2B

ETW 1001: Renovated 1st Floor Convenience with a Perfect Gulf View! 2BR/2B
Okaloosa Island
9.8 out of 10, Exceptional, (222 reviews)
ETW 1001: Renovated 1st Floor Convenience with a Perfect Gulf View! 2BR/2B

13. Beachview Complex - Steps from the beach, Swimming pool, and Tennis Court

Beachview Complex - Steps from the beach, Swimming pool, and Tennis Court
Navarre
10.0 out of 10, Exceptional, (263 reviews)
"Great trip and short walk to the beach. Great location! Host very nice and attentive."
United States
Terry O.
The price is NZ$816
includes taxes & fees
13 Oct - 14 Oct
Beachview Complex - Steps from the beach, Swimming pool, and Tennis Court

14. Walk Out Your Door & Step Onto The Beach!

Walk Out Your Door & Step Onto The Beach!
Okaloosa Island
9.6 out of 10, Exceptional, (195 reviews)
"There was a strong musty smell however good place to stay"
United States
Brittany K.
The price is NZ$850
includes taxes & fees
11 Oct - 12 Oct
Walk Out Your Door & Step Onto The Beach!

15. Nautilus 2211 Gulf View 2 BR 2nd Flr, Sleeps 6, Free Beach Service 3/1-10/31

Nautilus 2211 Gulf View 2 BR 2nd Flr, Sleeps 6, Free Beach Service 3/1-10/31
Okaloosa Island
10.0 out of 10, Exceptional, (9 reviews)
"The room was very clean and just as pictured,fully stocked kitchen made meals easy. The view from master bedroom balcony was better than expected. Beach access was easy and the beach service was a added bonus with the extra chairs and cooler. Would 10/10 recommend staying here, with 3 kids it was an ease and very enjoyable."
United States
Justin D.
The price is NZ$879
includes taxes & fees
16 Oct - 17 Oct
Nautilus 2211 Gulf View 2 BR 2nd Flr, Sleeps 6, Free Beach Service 3/1-10/31

16. Beachfront Condo, 10 Steps to the Sand

Beachfront Condo, 10 Steps to the Sand
Okaloosa Island
10.0 out of 10, Exceptional, (97 reviews)
"Awesome place right on the beach…literally, 10 steps to the sand….and about a 2 minute walk across the beach and you’re literally standing in the water. My wife I stayed a full week here and we had an awesome time with the beautiful sunrises and sunsets, not to mention the white sands and emerald/turquoise water, it was just beautiful...so beautiful, we didn’t want to leave. The condo had nice decor, was clean and equipped with a fully loaded kitchen, clean bathroom and bedroom. Communication...
United States
Sidney
The price is NZ$622
includes taxes & fees
2 Oct - 3 Oct
Beachfront Condo, 10 Steps to the Sand

17. A305 Waterscape, Gulf Views; 2 K's, Bunks, Bch Service! Wonderful for Snowbirds!

A305 Waterscape, Gulf Views; 2 K's, Bunks, Bch Service! Wonderful for Snowbirds!
Okaloosa Island
9.8 out of 10, Exceptional, (233 reviews)
"View from the balcony was great. Could view the fireworks and ocean great!"
United States
Jordan W.
The price is NZ$1,006
includes taxes & fees
28 Oct - 29 Oct
A305 Waterscape, Gulf Views; 2 K's, Bunks, Bch Service! Wonderful for Snowbirds!

18. BEAUTIFUL GULF FRONT CONDO AMAZING VIEW NOW RESERVING OCTOBER 2026 - 2027;

BEAUTIFUL GULF FRONT CONDO AMAZING VIEW NOW RESERVING OCTOBER 2026 - 2027;
Okaloosa Island
10.0 out of 10, Exceptional, (137 reviews)
"Great stay. Unit is very nice/clean and the view of the beach is great. Would stay again."
United States
Chris F.
The price is NZ$728
includes taxes & fees
31 Oct - 1 Nov
BEAUTIFUL GULF FRONT CONDO AMAZING VIEW NOW RESERVING OCTOBER 2026 - 2027;

19. Top floor! Complimentary beach chairs! Amazing view!

Top floor! Complimentary beach chairs! Amazing view!
Navarre
9.4 out of 10, Exceptional, (142 reviews)
"Amazing property with amazing views!"
United States
Nick B.
The price is NZ$691
includes taxes & fees
25 Oct - 26 Oct
Top floor! Complimentary beach chairs! Amazing view!

20. Salty Soul- Waterfront w 2 Kings! Minutes to the Gulf. Pool,Beach gear,W&D.

Salty Soul- Waterfront w 2 Kings! Minutes to the Gulf. Pool,Beach gear,W&D.
Okaloosa Island
10.0 out of 10, Exceptional, (14 reviews)
"Salty Soul was a beautiful condo, well stocked with items to make our stay comfortable. We loved being walking distance to the beach and appreciated the beach essentials that were provided- made our beach days very enjoyable. The heated pool and hot tub were also nice perks. We would love to stay again if returning to the area. "
United States
Stacey
The price is NZ$936
includes taxes & fees
2 Oct - 3 Oct
Salty Soul- Waterfront w 2 Kings! Minutes to the Gulf. Pool,Beach gear,W&D.
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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Top Santa Rosa Island Hotel Reviews

Find out more about Santa Rosa Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Santa Rosa Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Santa Rosa Island. 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 Santa Rosa Island. 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 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 holiday 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 Santa Rosa Island short-term rentals, that won’t be hard to do.

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