
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.

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

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, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.

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.

Beachside-Top Floor-Pools-Gym-Destinwest Gulf 604
BEACHSIDE CONDO ON OKALOOSA ISLAND on Florida's Emerald Coast. Named as one of the top 10 “Best beaches in the US” and a great location for vacation. Surrounded by crystal clear emerald waters and sugar white beaches, this top floor (6) condominium offers spectacular views of the gulf and the night lights of Okaloosa Island with breathtaking sunrises and sunsets over the gulf. This is your Best Beach Retreat! Imagine your "toes in the sand" all within a stones throw from your front door.

Destin West Resort, Lazy River & Free Beach setup
This is a 3-bedroom, 2-bath condo that sleeps 8 people plus a baby. Destin West Resort offers great amenities: 700-foot long Lazy River, 7 Pools (some heated seasonally), 4 Hot tubs, State-of-the-art-Fitness Center and beautiful beach! You also have access to a Marina(bring your boat), picnic areas, water sports/boating rental (next door). The skybridge gives you easy access to both sides of the resort. Walking distance to Adventure Zone, the Gulfarium, the Boardwalk and fishing pier.

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.

DestinWest Pelican Bayside, Lazy River, Hot Tub.
Master bedroom with bathroom, bunk room with bathroom (the bunk room has one bunk bed and no door), sofa sleeper. Balcony with lazy river and bay view. You will find everything here from Lazy River, seven pools (one heated, one with waterfall), hot tubs, zero entry pool, gym, bbq area. Next door is an arcade with virtual reality, bar and food. You have access to swim and play in both the ocean and the bay. It is a short walk to the Okaloosa boardwalk for shopping, restaurants and fun

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.

Waterscape A207/Free BCH SVC/2 Kings/75' TV
Waterscape Resort A207 (just steps to the beach & pools) ~ Ocean view from kitchen/Master BRs/living room/patio ~ FREE beach service (2 CHRs+umbrella) during 3/1-10/31 ~ 2 King BRs with their own en suite + 1 half bath in the living area ~ One bunk room with a DOOR for privacy (two twin beds) ~ Q pullout sleeper ~ Pack 'n Play ~ Highchair ~ 4 smart TVs (1x75’’, 2x50’’, and 1x32’’) ~ Upgraded appliances & quartzite countertops ~ Tiles throughout ~ Washer/dryer in unit

Fully Remodeled Beach Condo with Amazing Views
Welcome to your premium vacation rental at the Pelican Beach Resort!!! This 16th-floor condo is decorated in a beach theme, serving both modern and traditional coastal styles. Located directly on the white sands of Destin, it offers unobstructed and boundless views of the beach and the ocean. The initial remodeling process has been completed in 2020, and lots of new upgrades have been completed by the end of 2022. It is a perfectly refreshing getaway for your family!

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!

Simple Fort Walton Beach Waterfront Studio Condo
Relax and unwind in this stylish and cozy studio in the heart of Fort Walton Beach! Surrounded by delicious restaurants and bars, this studio is perfect for a romantic getaway or a solo trip. You'll love the breathtaking views of the bay from the sun-drenched balcony, where you can enjoy your morning coffee or a glass of wine at sunset. With all the amenities and stunning views, this studio is the perfect place to make memories and create a home away from home.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Sugar Sand Cottage at Destin Pointe

Its 5 o'clock here

Waterview Villa, Steps to the Sand, King Bed, Pool

Pool - Block to Beach - Golf Cart - Beach Service

Summer Specials *Fully Loaded* Pool & Hot Tub

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Harbor Central Penthouse

#1 4BR HUGE PET Friendly Home Away from Snow!
Condo rentals with a pool

Oceanfront 3 King BR/3BA Condo Steps 2 Sand & Surf

Amazing Top-Floor Condo, Free Beach Service!

Ground floor! Waterfront condo at Pirates Bay!

Emerald Grande 4BR~Corner Unit Wrap Around Balcony

Soundside Waterfront Condo

Beach Penthouse on Okaloosa Island in FWB, FL

1203 Oceanfront Pelican Beach: Pools/HTubs Fab Loc

Okaloosa Island condo *free beach service
Other vacation rentals with a pool

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

Clean & Luxurious Beachfront ~ 7 Pools+HotTubs+Gym

Nautilus 2311 Gulf View 2BD/2BA 3rd Floor. Free

Last Min June Deal! Pool, Beachfront, Beach Gear

Luxury Beach Front Condo! 3bd/3ba-Waterscape(A301)

Stunning sunsets! 206 Islander condo w/ Gulf views

Aloha Pool House- Stay Local, Live Aloha

Gulf Side 602 Pet friendly gulf front condo
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 | G$33,891 GYD | G$38,284 GYD | G$46,861 GYD | G$47,070 GYD | G$48,116 GYD | G$59,622 GYD | G$63,806 GYD | G$44,978 GYD | G$39,748 GYD | G$38,493 GYD | G$34,518 GYD | G$33,681 GYD |
| 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 2,670 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at G$14,644 GYD per night before taxes and fees

Verified guest reviews
Over 52,240 verified reviews to help you choose

Family-friendly vacation rentals
2,020 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
1,560 properties have a dedicated workspace

Wi-Fi availability
2,660 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, Gulfarium Marine Adventure Park, and Crab Island
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Aqua Resort
- Seacrest Beach
- Opal Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- HarborWalk Village
- Fort Walton Beach Landing
- The Boardwalk on Okaloosa Island
- Henderson Beach State Park
- Topsail Hill Preserve State Park
- Shipwreck Island Waterpark
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Pier Park
- Gulf World Marine Park
- Jade East Towers





