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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.

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Guest favourite
A comfortable living area features a light-colored sofa with decorative pillows, accompanied by a round wooden coffee table. Natural light filters in through large windows, illuminating the space. A small dining table with light chairs is positioned nearby, enhancing the cozy atmosphere.
Condo in Santa Rosa Beach
4.91 out of 5 average rating, 183 reviews

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

Superhost
A light-filled studio features a spacious bed with soft linens and decorative pillows. A comfortable sofa is positioned nearby, and sliding glass doors lead to an outdoor area with views. Light tile flooring complements the warm yellow walls, adding to the inviting ambiance.
Condo in Fort Walton Beach
4.88 out of 5 average rating, 164 reviews

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!

Guest favourite
A vibrant living area features a light-colored sofa paired with a matching armchair. A circular coffee table sits between, while a dining table with four chairs is positioned nearby. Walls are decorated with subtle aquatic-themed artwork, and light streams in from multiple sources, enhancing the bright ambiance.
Condo in Fort Walton Beach
4.94 out of 5 average rating, 236 reviews

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!

Guest favourite
A large, mickey-shaped pool is surrounded by lounge chairs and tropical landscaping. In the background, the waterway can be seen, framed by palm trees and extending toward the horizon under a clear blue sky.
Condo in Fort Walton Beach
4.9 out of 5 average rating, 429 reviews

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.

Guest favourite
A balcony features a dining table set with two glasses and a bottle, overlooking the beach. Lounge chairs and umbrellas are visible on the sandy shore, with the Gulf of Mexico's turquoise waters in the background, highlighting direct beach access.
Condo in Fort Walton Beach
4.95 out of 5 average rating, 134 reviews

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.

Top guest favourite
A table set for refreshments showcases a spread of crackers, cheese, fruits, and chilled water with lemon. In the background, the emerald waters of the Gulf are visible, with beach umbrellas dotting the shoreline under a partly cloudy sky.
Condo in Fort Walton Beach
4.99 out of 5 average rating, 102 reviews

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

Superhost
The image captures a sprawling resort pool area lined with palm trees, inviting lounge chairs, and winding waterways. A mix of tranquil pools is observed, with gentle steps leading into the water and vibrant blue shades reflecting the clear skies.
Condo in Fort Walton Beach
4.86 out of 5 average rating, 118 reviews

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.

Top guest favourite
A serene twilight view captures the sky filled with clouds reflecting subtle shades of orange and blue. The marina lights twinkle along the water's edge, while the horizon highlights an array of colors as day transitions into night.
Condo in Fort Walton Beach
4.97 out of 5 average rating, 192 reviews

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.

Top guest favourite
A private balcony is featured, showcasing a round table with two chairs. The expansive view includes the Gulf waters and sandy beach under a partly cloudy sky with sunlight reflecting off the water.
Condo in Fort Walton Beach
4.94 out of 5 average rating, 175 reviews

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!

Guest favourite
A view of the Gulf can be seen through vibrant blooming flowers and palm trees. A wooden pergola is present in the background, with sun loungers visible at the pool area, creating a serene coastal atmosphere.
Condo in Fort Walton Beach
4.93 out of 5 average rating, 182 reviews

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.

Guest favourite
Condo in Fort Walton Beach
4.88 out of 5 average rating, 154 reviews

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

Top guest favourite
A serene view of the beach features soft white sand leading to the emerald waters of the Gulf of Mexico. Beach chairs are arranged in a neat line along the shore, enhancing the tranquil atmosphere. The sky is clear, adding to the inviting coastal scene.
Condo in Fort Walton Beach
4.74 out of 5 average rating, 518 reviews

Emerald Waters & Sugar White Sand!

Enjoy all the comforts of a North American lifestyle with a modern contemporary look and stunning Gulf-front views from our high-floor corner unit. Located right on the beach with no roads to cross and close to Destin. High-speed Wi-Fi, keyless entry, smart TV, beach towels, starter amenities, a seasonally heated Gulf-front pool (March 1–April 30 & Oct 1–Dec 31, subject to change) and MORE. Have a sunny day!

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

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Avg. price$216 CAD$231 CAD$304 CAD$315 CAD$322 CAD$399 CAD$515 CAD$343 CAD$299 CAD$271 CAD$221 CAD$213 CAD
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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 $70 CAD 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 and kid-friendly amenities

  • Pet-friendly vacation 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 vacation 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