
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.

Relaxing Gulf Front Couple's Retreat*Beach Service
Welcome to Okaloosa island! Come experience gorgeous Direct Beachfront unobstructed views! This studio has everything you need for a fabulous beach getaway! Private balcony. Just seconds to beautiful beach & Gulf. 2 Chairs & Umbrella have been purchased for you w/ full beach service$50/day value (Mar-Oct)for a beautiful beachy day! 4 min drive to dining. Lg pool. LVP flooring*2022*Couch*2022*Premium foam mattress*2022 Spotless w/Low Cleaning Fee! Must be 22 years old to book w/ proof of ID

1bd/2ba condominium on the ground floor~ Right on
5-7 minute walk to the beach~fitness center and pool on property~10% off for golf cart rentals~ Walking distance to restaurants~ 2 beach backpack chairs provided~one beach wagon~2 beach towels Stay at ‘Happy Hour Hideaway’ & leave your worries behind! Located on infamous Highway 30a, you will love staying so close to the action while still enjoying the seclusion of this complex. This is a 1Bedroom + hallway bunks/ 2 bathroom condo, located on the first floor of the complex. For your conveni

Ground floor! Waterfront condo at Pirates Bay!
Clean, updated waterfront condo at Pirates Bay in FWB! Excellent ground floor, walkout unit. We have smart locks, allowing for easy self check-in. The patio sits just off the resort pool and just steps to the marina and BBQ grills. Pirates Bay is a wonderful waterfront resort community and the west facing unit allows beautiful sunset views over looking the Santa Rosa Sound. Perfect location for everything in Ft Walton Beach and Destin! Public beach access on Okaloosa Island is a short drive!

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

Free Chair Service-Beachfront 6th Floor
Beautiful sixth-floor balcony views of beachfront, barrier island chain, and sound area! Exceptionally convenient white-sands beach access and gorgeous emerald waters! Enjoy the indoor/outdoor pool and on-site gym. This beach condo is not only fantastically located on the quieter end of Okaloosa Island, but also comes with modern, coastal-themed furnishings. Access the Destin and Fort Walton Beach attractions only a few miles down the street. Includes free chairs and umbrella on the beach!

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.

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.

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 BREATHTAKING 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.

"The Golden Sun" condo
"The Golden Sun." A luxury and calm stay in a 4th-floor condo only steps from the beach. Enjoy golden sunsets from the balcony that oversees the beach! Fast wifi with Alex integration(not offered by most condos). This features 1 bed and 1 sofa bed for a 4 person stay. 2 full bathrooms. A nice small kitchen so you can cook! Two TVs with Rokus for streaming. Small community grills for BBQ and a beautiful pool!

So Fire, So Good *Heated Pool*LakeView*Fireplace*
You’ll be saying our place is “So Fire, So Good” after your first night in our relaxing & stylish 1 bedroom, 1 bath space! Enjoy stellar lake views from the private balcony and cozy up by the custom-built fireplaces. Accommodating up to 6 guests and 2 pets (with a pet fee), this condo is located just ¾ mile from the beach - perfect for your next Destin getaway with friends or family!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin Retreat: Oceanview Poolside Luxury Condo

Sugar Sand Cottage at Destin Pointe

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

Oceanview | Pool | Private Beach | Golf Cart

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

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Mahi Bay * Beach Boat Slip Fishing Dock 1st Floor

Luxury 30A Cottage w/ Private Pool and Golf Cart
Condo rentals with a pool

Pelican Beach Resort, 7th Flr, Amazing Beach Front

Majestic Sun B211*Golf Cart Included*Heated Pools*

Destin West Penthouse Bay, Roof Top terrace

Hidden Gem on the Beach - Coastal Luxury!

Beachfront, 7th Flr at Pelican, Breathtaking Views

Beachfront - Amazing View - Newly Remodeled!

Pool paradise with 75" TV - close to beach

Ocean Front, Corner Unit, Wi-Fi, 2BR, 2 BA
Other vacation rentals with a pool

Waterfront Condo | Pool, Marina & Near Destin

1505 Oceanfront Pelican Beach Fab Loc Pools/HTubs

1 BR + 1.5 BA + Pontoon + Pickleball Fun

Gulf Front #2002 ETW 3King /3Bath Renovated

B210 Pirates Plunder

Destin West Villa ~ Hot Tub,on Rooftop Terrace

Amazing View Beach Front Condo

25% Off-No Service Fees-Remodeled Beachfront - Ste
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 | € 132 | € 142 | € 187 | € 194 | € 198 | € 245 | € 317 | € 211 | € 184 | € 167 | € 136 | € 131 |
| 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 € 43 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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- Rentals with pools Okaloosa County
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- 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
- Raven Golf Club
- Eglin Beach Park
- 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