
Holiday rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Santa Rosa Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Beach Penthouse on Okaloosa Island in FWB, FL
Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

GULF FRONT TopFloor Amazing VIEW Directly On Beach
Cozy oasis with a view that takes your breath away! You'll enjoy relaxing on the private balcony overlooking the ocean. King bed and twin pullout loveseat. Beautifully renovated kitchen and bath. Fully stocked kitchenette with granite countertops. The full sized refrigerator is a special perk in this Luxury Honeymoon suite. Charming coastal accents throughout. Special attention has been given to this unit to ensure everything is top notch with professional upgrades. Waves roll in, cares roll out

Direct Beachfront Condo with pool
Relax and getaway to this beachfront condo retreat on Okaloosa Island in Fort Walton Beach, Florida. Just steps to the sugar-white sand and emerald Gulf coast waters, this updated 2BR/2BA condo features a private balcony with dolphin & sunset views, modern kitchen, Wi-Fi, washer/dryer, and pool (heated in the winter). Free beach service (2 chairs + umbrella, Mar–Oct). Only 5 miles to Destin! Please note - Roof repairs for the condo are ongoing from 2/16/2026 and expected to be completed May 5/

Beachfront Bliss! Gulf Waves at The Palms #201
Nestled on shimmering Gulf shores, The Palms #201 invites you to unwind with jaw-dropping oceanfront views. This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat. Steps from the water, this guest favorite blends relaxation and rejuvenation for a home-away-from-home feel. From March through October, we provide complimentary beach service with two chairs and umbrella—a $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

Waterfront Studio • Santa Rosa Sound • Sunsets
Enjoy breathtaking views of the Santa Rosa Sound and marina from your private top-floor balcony in this waterfront studio. Whether you're sipping coffee at sunrise or watching vibrant sunsets each evening, this spot delivers unforgettable costal charm in a quiet, peaceful setting. Perfect for couples or solo travelers, the studio features a full bath with tile shower, well-equipped kitchenette and sparkling pool. Gulf beaches are a just a short drive away. Free parking and easy self check-in.

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach
Newly renovated! - Welcome to The Oasis, a luxury beach studio at El Matador Condos on Okaloosa Island, Fort Walton Beach, FL. Be our guest at this beautifully decorated, clean, comfortable studio, ideal for small families, small groups, couples, singles, & business travelers. You'll have direct access to the private beach & all the amenities including a seasonally heated outdoor pool, Gulf view pool, hot tub, sauna, gym, tennis/pickleball & basketball court, BBQ areas, & a laundry room.

One Step to the Beach!
"One Step to the Beach" Highlights: - Beachfront Condo at Surf Dweller - First Floor - Pull Up to the Front Door and Unload - Free “Platinum” Beach Service: 2 Beach Chairs, Umbrella + Kayak / Paddleboard access (Mar-Oct) - Two Parking Spaces - 1 King Bed - Master Suite - 2 Queen Beds - Second Bedroom - Cable + Streaming - WiFi - Keurig and Drip Coffee Makers - Seasonal Heated Pool - Tennis/Pickleball Courts - Washer and Dryer in the Condo - Pack n' Play - Shopping / Restaurants Nearby

Retreat by the Sea at Seacrest Condo
Welcome to Retreat by the Sea. This studio is at Seacrest Condominiums located directly on the beach on beautiful Okaloosa Island in Fort Walton Beach six miles from Destin. Relax on the balcony and enjoy the beautiful views of the Gulf and amazing sunrises and sunsets. You have direct access to the beach and all the amenities that the condo has to offer including indoor/outdoor pool, gym and bbq area. This amazing studio also has a kitchenette, mini-refrigerator and private laundry.

Lovely beach-front condo with free beach setup.
As soon as you enter our 3rd floor beachfront condo, you will leave all your cares behind and unwind while enjoying a direct view of the Gulf of Mexico. You can walk to the beach straight out of the building, no need to cross any roads. Many updates done in March 2021: brand new queen size sleeper sofa bed, brand new stainless steel refrigerator, range, dishwasher and microwave, brand new furniture, new paint, new flooring, and brand new TV's. We have Netflix and high speed WiFi.

DestinWest G405 Kid-friendly/oceanview/Lazyriver
[new patio furniture] Destin West Resort Gulfside 405 (2mins to the beach and pool) ~ 1 Bdr + 1 bunkroom with 2 full baths, Sleeps 6 ~ great ocean view ~ free beach service: 2 chairs & 1 umbrella (seasonal: 3/1 - 10/31, 9am-5pm) ~ 1 King Bdr with a private bathroom ~ 1 bunk room (2 twin beds, each with its own TV) with a private bathroom ~ 1 Q pullout sleeper ~ pack n play ~ 4 smart TVs ~ full kitchen stocked with cookware (Keurig and a traditional coffee maker). ~ washer/dryer

Spacious, elegant, beachfront, w/office
* Huge oceanfront lanai * Free beach service April 1-Oct 31 *Adult/Kiddie pool; tennis *Private office space in the condo *High chair/pack-n-play *Huge 1453 sq ft *Fully stocked kitchen incl. air fryer *Near Destin but WAY less crowded *South facing for sunrise & sunset (seasonal) & sometimes dolphins! *Open the door to your private lanai for REAL white noise of the ocean waves

Kid-friendly! Lazy River~Skywalk over to beach!
This is a beautiful one bedroom condo plus bunk area located on Bayside of Destin West! The unit comes equipped with a beach cart to make the short walk to the beach even easier! You will love the location of this unit! Freshly painted, with beautifully decor, plus beach towels (2) - you will feel right at home at our 'Salty sandpiper'. With a fully stocked kitchen, washer and dryer, and a lazy river pool - this condo is the perfect place for your beach getaway!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Sugar Sand Cottage at Destin Pointe

5 BD Miramar Beach House| Walk to the Beach + Pool

Harbor Central Penthouse

Isle Be Back! Miramar Beach Villa! STEPS TO BEACH!

#1 4BR HUGE PET Friendly Home Away from Snow!

Pool Retreat Near Destin Beach

All you need! Location | Golf Cart | Walk to Beach

SUNDESTIN BEACH RESORT 912, BEACHFRONT
Apartment rentals with a pool

The Merry Whale on The Emerald Coast

Sea Oats*Beachfront View!2Bdr/2Bath, Sleeps 6

WaterScape Now Booking 2026! Beach/resort/pool/spa

Beautiful Emerald Beach Condo

Gorgeous 2BR With Panoramic Water Views

Condo across the street from the gulf

Serene Panoramic Views of the Gulf

Ocean Views at Waterscape Resort!
Other holiday rentals with a pool

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury

Venus by the Sea – Unit #103

Sandy Cheeks/Okaloosa Island

Seaside getaway !

Stunning sunsets! 206 Islander condo w/ Gulf views

314 Island Princess - Beach, Pool, Spa, Balcony!

Okaloosa Island condo *free beach service

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £117 | £125 | £165 | £171 | £175 | £216 | £232 | £163 | £144 | £140 | £125 | £122 |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°C |
Quick stats about holiday rentals with a pool in Santa Rosa Island

Total holiday rentals
Explore 2,620 holiday rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 55,720 verified reviews to help you choose

Family-friendly holiday rentals
1,900 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
1,570 properties have a dedicated workspace

Wifi availability
2,610 of Santa Rosa Island holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Santa Rosa Island rentals

4.7 Average rating
Santa Rosa Island stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Santa Rosa Island’s top spots include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park and Crab Island
Destinations to explore
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- Rentals with pools Okaloosa County
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Pensacola Beach
- Opal Beach
- Frank Brown Park
- Johnson's Beach, Gulf Islands National Seashore
- Navarre Beach Fishing Pier
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- Village of Baytowne Wharf
- Henderson Beach State Park
- Camp Helen State Park
- Shipwreck Island Waterpark
- Gulfarium Marine Adventure Park
- The Track - Destin
- HarborWalk Village
- Gulf World Marine Park
- Topsail Hill Preserve State Park
- The Boardwalk on Okaloosa Island
- Aqua Resort
- Destiny East
- Jade East Towers




