
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.

Sandestin Resort Studio, Spectacular Bay Views
Our Bayside Studio offers spectacular panoramic views of Choctawhatchee Bay. Located in Sandestin Resort on a quite enclave framed by Florida pines and the fairways of The Links Course, your own personal balcony on the third floor serves as the perfect viewpoint of the Bay. Guests and children will enjoy our relatively low nightly rates but also have access to all the amenities Sandestin has to offer (Beach, golf, tennis, water-sports, spa, nature trails, many kids activities, dining, shopping).

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

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, .

Steps from Sand - Fort Walton Beach
Welcome to the Nautilus on Okaloosa Island! Enjoy an ocean view from this 2nd floor balcony where you are only steps away from sugar white sand beaches. This two bedroom, two bath condo is the perfect place for your beach vacation. The unit has everything you need, including a washer and dryer. Enjoy the nearby restaurants, shopping and heated pool. This destination will not disappoint! On-site amenities included: Heated pool Private beach access Complimentary Parking BBQ Grills And more!

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

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.

Studio in Sandestin/ Free parking/Free beach tram
Sleeping up to 4 guests, this studio provides everything you will need for a perfect beach vacation while indulging in the luxurious resort life. Sandestin Golf and Beach Resort features over seven miles of beaches, a pristine bay front, four championship golf courses, 15 world-class tennis courts, a 226-slip marina, a fitness center, a spa, and celebrity chef dining. Enjoy the fun and entertainment at The Village of Baytowne Wharf with shops, restaurants, playgrounds & more!

Sunshine and beach time /Okaloosa Island
THANKSGIVING 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

Okaloosa Island Gulf View Resort Studio w/ Balcony
Escape to the stunning white sand beaches of the Gulf of Mexico and stay in this charming studio condo on Okaloosa Island! Located in the popular Islander Beach Resort, this unit is newly renovated and boasts breathtaking views of the emerald green waters. Step outside onto your private balcony to watch the sunset or enjoy your morning coffee with the sound of the waves. Book your stay today and experience the best of the Florida panhandle!

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 BREATHTAKING views of the Gulf & white sand beaches with the perfect sunset view from the balcony!

Waterfront Paradise•Snowbird Rates Available
Beautiful studio condo, centrally located in Ft Walton Beach. Condo is waterfront to the Santa Rosa sound which is adjacent to the Gulf. The condo overlooks a large inviting pool. Walking distance to restaurants. Okaloosa Island & Destin beaches, attractions and shopping are only 10-15 min away. Navarre is 20 min away.Condo is on the 2nd floor with elevator access. Private marina. Starter pack of supplies provided
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin Retreat: Oceanview Poolside Luxury Condo

Fall Escape! Private Beach, Heated Pool, 2 Kings!

WATERFRONT~Home~PRIVATE~POOL & DEEP DOCK bring 🚤⛵️⚓️

Oceanview | Pool | Private Beach | Golf Cart

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Destin's most adored home!

Waterfront Home-Dock, Pool, Kayaks, Dogs Welcome!

Mahi Bay * Beach Boat Slip Fishing Dock 1st Floor
Apartment rentals with a pool

"SeaGlass" - Oceanfront with expansive balcony.

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

Penthouse Paradise on Okaloosa Island

Beach Side 1/1 Condo Paradise

Beachfront - Amazing View - Newly Remodeled!

Ocean Front, Corner Unit, Wi-Fi, 2BR, 2 BA

Pool paradise with 75" TV - close to beach

Stylish Top-Floor Condo, Free Beach Service!
Other holiday rentals with a pool

Last Min Nov Deals! Beachfront, Pool, Gulf Views!

1 BR + 1.5 BA + Pontoon + Pickleball Fun

B210 Pirates Plunder

Stunning Ocean Vibes Retreat

Destin West Villa ~ Hot Tub,on Rooftop Terrace

Pristine Pool and Water View!

POOL and Heated SPA-Bluefish #4 - OKA Island 2BR

Gorgeous Views & Pristine Pool! Walk to downtown!
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 ÂŁ37 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 & child-friendly amenities
Pet-friendly holiday rentals
Find 110 rentals that welcome pets
Rentals with dedicated workspaces
1,680 properties have a dedicated workspace
Wifi availability
2,550 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, Crab Island and Gulfarium Marine Adventure Park
Destinations to explore
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- Villa rentals Santa Rosa Island
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- Fitness-friendly rentals Santa Rosa Island
- House rentals Santa Rosa Island
- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- Destin Harbor Boardwalk
- Crab Island
- 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
- Raven Golf Club
- Pensacola Beach Crosswalk
- Gulfarium Marine Adventure Park
- Fort Walton Beach Golf Course
- Walton Dunes Beach Access
- Camp Helen State Park
- Pensacola Dog Beach West
- The Track - Destin
- Fred Gannon Rocky Bayou State Park
- Shipwreck Island Waterpark
- Wayside Park, Okaloosa Island
- Seacrest Beach
- Gulf World Marine Park