
Vacation 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.

Waterscape 4th Flr 1 Bedroom w Bunks on the beach
Relax in this beautifully decorated 1BR/2BA condo at Waterscape Resort with 4th-floor views of the courtyard, heated pool, and partial beach/ocean views. The master bedroom features a king bed and en-suite bath. Kids love the bunk beds with TVs. The unit also includes a sofa bed, stainless steel appliances, new flooring, in-unit washer/dryer, and beach chairs with an umbrella. Many repeat guests return for the bunk beds and resort amenities, including three pools, a waterfall, and a lazy river.

Destin West, Bayside, 2 BR+ Bunk Room, sleeps 8
GREAT VIEWS!!! Sandpiper unit 502 has 2 bedrooms, two baths, and a private bunk-bedroom, so its really a 3 BR...sleeps 8. It is furnished with a new sofa sleeper and matching couch in family room. All of this is designer furnished condo accommodates up to eight people to sleep. The interior of the unit reflects a classic, high-end feeling. Walking distance to many restaurants and activities. My place is close to restaurants and dining, the beach is 5 minute away over elevated walkway, .

Beachfront! Newly remodeled! Right on the beach!
Beachfront top floor unit, on a private beach, in two story building gives unobstructed sunset/ocean views. Located on soft white sand with on-site free parking. Perks of choosing this unit include gated resort with pools, beach service included (Mar.-Oct.), tennis courts, pickle ball, and par 3 golf course (included). Unit has fully functional kitchen and wifi included. Master bedroom beach/sunset views! Sleeps 4 adults with use of sofa bed in living area and additional cot-sized bunkbeds.

Oceanfront 3BR/3BA Condo | Steps to Sand & Surf!
Experience the Gulf in a Newly Remodeled Condo! This family-friendly ground-floor unit offers ultimate convenience. The master bedroom has ocean views, a king bed with a pullout trundle. The second bedroom has a king bed with a trundle, and the third has a queen bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

Relaxing Soundside Condo - WataView!
Vacation or work at our comfortable waterfront kitchenette studio in the heart of Fort Walton Beach. The sugar white sand beaches are just a short drive away, and adventure awaits right at your doorstep on Santa Rosa Sound. Includes pool and marina! Boat slip (28 Ft) available! The unit has a queen bed and futon that lays down to a full size bed. It's very comfortable for small groups. We are real owner-hosts and strive to keep our unit spotless and well supplied for our cherished guests.

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA
Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the beach. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, pool, BBQ pits and parking area (a parking pass is needed), but you will probably spend the majority of your time on our large private balcony overlooking the pool and beach, listening to the waves.

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.

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

Perfect View on Santa Rosa Sound with 2 Pools!
Enjoy beautiful blue skies and gorgeous sunsets over the Santa Rosa Sound, while looking out over the marina from your very own private deck! This gorgeous studio unit has one of the best views in the entire 120 room complex! Located in the preferred A building, this Non-Smoking, NO PETS ALLOWED, sparkling clean top floor unit has a beautiful bathroom with full size tile shower and newer plumbing fixtures. Marina slip is not available for rent at this time.

Sunshine and beach time /Okaloosa Island
CHRISTMAS at the BEACH! Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). Fully furnished, ( USB port outlets, no carpet, stainless appliances, and keyless entry). A one minute walk to the white sand, wifi in the unit, 2 beach chairs, cooler, beach towels, and beach umbrella. Laundry onsite, Tom Thumb next door for items you might need. Everything for a great beach vacation! 683 Nautilus court

Gulf View Studio condo Fort Walton Beach
Islander 705 Studio condo with a beautiful Gulf view on Okaloosa Island. This 7th floor unit sleeps 2 and includes - 1 King bed - 1 sofa sleeper - 1 Full bathroom (glass shower) - Keurig Mini - 1 full kitchen with stove, refrigerator, microwave, dish washer Complimentary beach service 2 chairs and 1 umbrella included March - October! Enjoy amazing views of the Gulf & white sand beaches with the perfect sunset view from the balcony!

Sea Shell at Sunset Cottages - Beach Service Inc
Sea Shell condo is located in the 19 unit Sunset Cottages complex on Okaloosa Island in Fort Walton Beach, FL. “Gulf Side”, just over 200 steps from the sand, no roads to cross, relaxing on the beach in minutes! The Sea Shell has 2nd floor partial gulf views from the dining room window, and both balconies. Inside is a spacious 750 sq.ft. to lounge and relax including; large great room, large bedroom and bath, condo built in 2000.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin Retreat: Oceanview Poolside Luxury Condo

Santa Rosa Beach Canopy House with pool

Sugar Sand Cottage at Destin Pointe

Book Holiday! Private Beach, Heated Pool, 2 Kings!

#2 4BR HUGE PET Friendly Home Away from Snow!

Gulf Breeze: 5MinWalkToBeach,Pool,Yard, CloseToAll

Harbor Central Penthouse

SUNDESTIN BEACH RESORT 912, BEACHFRONT
Condo rentals with a pool

Majestic Sun A711*Remodeled*Golf Cart*Heated Pools

Soundside Waterfront Condo

"SeaGlass" - Oceanfront with expansive balcony.

R&R Coastal Condo

No Airbnb Fees! | Incredible View | Free Parking

Seascape Ocean View Walk 2 Beach - Heated Pools

Free Chair Service-Beachfront 6th Floor

Island Paradise on Okaloosa Island
Other vacation rentals with a pool

Waterscape A127 - Free Beach chairs & Lazy River!”

Beach Front Penthouse, Stay Salty, Free Activities

Pool Table, Lazy River & AmazingViews! Destin West

It's a SHORE Thing- water views from every room!

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

1 BR + 1.5 BA + Pontoon + Pickleball Fun

Waterscape A202-Emerald Vista-2bd+bunks Ocean View

Destin West Villa ~ Hot Tub,on Rooftop Terrace
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 | ﺩ.ﺇ566 | ﺩ.ﺇ606 | ﺩ.ﺇ797 | ﺩ.ﺇ826 | ﺩ.ﺇ845 | ﺩ.ﺇ1,047 | ﺩ.ﺇ1,120 | ﺩ.ﺇ790 | ﺩ.ﺇ698 | ﺩ.ﺇ709 | ﺩ.ﺇ580 | ﺩ.ﺇ558 |
| 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 vacation rentals with a pool in Santa Rosa Island

Total vacation rentals
Explore 2,550 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 55,400 verified reviews to help you choose

Family-friendly vacation rentals
1,850 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
1,680 properties have a dedicated workspace

Wi-Fi availability
2,550 of Santa Rosa Island vacation rentals include wi-fi 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, Crab Island, and Gulfarium Marine Adventure Park
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- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- 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
- Fort Walton Beach Golf Course
- Gulfarium Marine Adventure Park
- Eglin Beach Park
- Raven Golf Club
- Walton Dunes Beach Access
- Camp Helen State Park
- The Track - Destin
- Pensacola Dog Beach West
- Fred Gannon Rocky Bayou State Park
- Seacrest Beach
- Shipwreck Island Waterpark
- Wayside Park, Okaloosa Island




