
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.

Panoramic Gulf Views! | 3 Kings
"Panoramic Gulf" Highlights: - Beachfront Condo at Island Princess - Corner Unit, Second Floor - Gulf and Garden Patio Views - King Bed in Each Room - Custom Bunk Bed: Twin over King over Twin - Leather Sleeper Sofa with Upgraded Mattress - Free “Platinum” Beach Service: 2 Chairs, Umbrella, and Table + Kayak / Paddleboard access (Mar-Oct) - Cable + Streaming - Wifi - Seasonally Heated Pool - Washer/Dryer in the Condo - Keurig and drip coffee makers - Pack n' Play - Shopping / Restaurants Nearby

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.

One Block to Crystal Beach + Pool + King Bed + Convenient Location
- One block from the Crystal Beach area of Destin - 0.6 miles to Destin Commons w/ Whole Foods and shopping - 1.0 mile to Publix - This is the UPSTAIRS UNIT (downstairs rents separately through same host.) Each unit is fully separate. The Destin Doublemint, a bright and airy one-bedroom cottage, is the perfect spot for your beach vacation. It's less than a 2-minute walk to the sand, making it easy to pop back for a dip in the pool or a movie in the AC before walking back over for sunset.

Stylish Coastal Baytowne Studio Amazing Amenities
Enjoy a stylish experience at this centrally-located studio on the Sandestin Resort right in the heart of the action of Baytowne Wharf Village. Newly renovated Welcome to paradise! Unit is located on the 5th floor of Pilot House allowing quick walking access to entertainment, food and pool. Only 10 minutes from the beach without ever leaving the Resort, Including Free Tram! The unit offers a King bed with luxury linens. Comfortable queen sofa that will fit two more guests or children.

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.

Waterscape 5th Flr -Closest 1 Bedroom to the beach
Enjoy the best courtyard and ocean views from this 5th-floor 1BR condo, the closest 1-bedroom unit to the beach at Waterscape Resort. 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, in-unit washer/dryer, and beach chairs with umbrella stored in the unit. Guests return year after year for the views, comfort, and resort amenities like pools, waterfall, and lazy river.

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.

Sleek & Sexy @ Sandestin Golf & Beach Resort
Newly remodeled pool & hot tub are now open!! TOP RATED 6th floor oceanfront studio at Sandestin Golf & Beach Resort's Beachside Two complex. Guests can enjoy dining, retail, entertainment, golf, tennis and other activities without leaving the gates of this 2400 acre resort on Florida's Emerald Coast. Sandestin Tram pass included. This property is highly ranked amongst Airbnb's Top 10% of homes based on ratings, reviews, and reliability.

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!

Island Princess 618 | Gulf Views & Beach Service
Experience the ultimate beach getaway at our renovated condo on stunning Okaloosa Island. This beachfront retreat features two spacious bedrooms, two modern bathrooms, and a rare oversized balcony perfect for soaking in the breathtaking views. Relax on the sugar-white sands and take in the emerald-green waters of the Gulf with complimentary beach service, including two chairs and an umbrella, provided from March 1st to October 31st.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Sugar Sand Cottage at Destin Pointe

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

FREEGolfCart!/HEATEDPool!/Walktobeach! Sleeps 10!

Serenity: 2 min to beach, Golf cart, Heated pool

PrivateTropicalOasisNearBeach-FreeGolfCartTilMar1

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

Fresh Fun Interior | New Golf Cart | Heated Pool

Harbor Central Penthouse
Condo rentals with a pool

Summer breeze house beach view

A129 Waterscape 1st floor,beach chairs& Lazy River

Gulf Front, Private Balcony, Heated Pool & Hot Tub

"SeaGlass" - Oceanfront with expansive balcony.

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

Bluefish: Pool, 3min Walk to Beach and Restaurants

1002 Oceanfront Pelican Beach Fab Loc Pools/HTubs

Relaxing Gulf Front Couple's Retreat*Beach Service
Other holiday rentals with a pool

Cozy Condo. Sunrise and Sunset

Nautilus 1605 - 6th Floor Gulf Front 1 Bedroom Fr

The Coastal Retreat

B210 Pirates Plunder

House w/ private heated pool, short walk to beach!

Gulf Views -Beach Chair Service -Resort Pool & Spa

Saltwater Pool/Spa, Cali King, BBQ, BEACH 4-miles

Luxurious BeachHouse Pickeball+HeatedPool+GolfCart
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 | $275 NZD | $295 NZD | $388 NZD | $402 NZD | $411 NZD | $510 NZD | $546 NZD | $385 NZD | $340 NZD | $345 NZD | $283 NZD | $272 NZD |
| 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 2,550 holiday rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island holiday rentals start at $89 NZD per night before taxes and fees

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

Family-friendly holiday rentals
1,850 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
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 holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Eglin Beach Park
- Pensacola Beach Crosswalk
- Raven Golf Club
- Gulfarium Marine Adventure Park
- Fort Walton Beach Golf Course
- Walton Dunes Beach Access
- Camp Helen State Park
- Fred Gannon Rocky Bayou State Park
- The Track - Destin
- Pensacola Dog Beach West
- Seacrest Beach
- Wayside Park, Okaloosa Island
- Shipwreck Island Waterpark




