
Holiday rentals with a pool in Santa Rosa Island
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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.

Waterfront cozy condo with king bed & resort pool
Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

1004 Oceanfront Pelican Beach: Pools/HTubs Fab Loc
1 Bed 2 Bath (Sleeps 6) NO PETS! Non-Negotiable rates. Location! Easy access to attractions! Direct access on the beach without having to cross the street. Pelican Beach Resort 1004 is a newly renovated 1-bedroom condo with stunning Gulf of Mexico views from your private balcony, an open-concept living area, and comfortable sleeping accommodations for up to 6 guests The fully equipped kitchen is designed with a bar that overlooks the living area for entertaining or enjoying a casual meal.

Amazing Top-Floor Condo, Free Beach Service!
Decorated in soothing designer colors with a coastal feel, the unit has 2 bedrooms with comfortable king size beds, flat screen TVs and private bathrooms; two bunk beds in a hallway alcove; 2.5 bathroom, and open concept full size kitchen with all new full size stainless steel appliances, dining area and living room with a sleeper sofa. The unit sleeps eight. Plus, you'll have access to all of Waterscape Resort's fabulous amenities! Complimentary beach service with 2 beach chairs and umbrella.

Star Of The Sea
Welcome to "The Star Of The Sea", Island Princess #312. Enjoy Gulf front views of the aqua blue waters of the Gulf with its sugar sand beaches from our beautifully decorated condo. Private balcony with access from family room and Master Bedroom. Fully stocked kitchen to prepare fabulous meals while taking in the views of the Gulf from the kitchen and dining area. Both master suites boast of comfort and access to private baths with full shower and tub amenities. Flat screen TV's in every room.

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 Panoramic Views Balcony Heated Pool
Beachfront Corner Condo in Destin - Panoramic Gulf Views Summer dates just released! Experience luxury in our Destin beachfront condo! This 3-bedroom, 2-bath unit offers panoramic Gulf views from the living area, kitchen, and master bedroom. Enjoy a renovated balcony, heated pool, tennis, basketball, pickleball, gym, and sauna. Beach chairs and umbrella included March-October. Convenient elevator and steps access. Book your Destin vacation rental now for an unforgettable beach getaway!

Cozy 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.

Retreat by the Sea at Seacrest Condo
Welcome to Retreat by the Sea. This studio is at Seacrest Condominiums located directly on the beach on beautiful Okaloosa Island in Fort Walton Beach six miles from Destin. Relax on the balcony and enjoy the beautiful views of the Gulf and amazing sunrises and sunsets. You have direct access to the beach and all the amenities that the condo has to offer including indoor/outdoor pool, gym and bbq area. This amazing studio also has a kitchenette, mini-refrigerator and private laundry.

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.

Ocean Views at Waterscape Resort!
Experience everything the stunning Emerald Coast has to offer while staying in our beautifully updated condo, with expansive ocean views including everything you need for a comfortable stay! Enjoy the Waterscapes resort amenities including direct beachfront access, beach chairs & umbrella, lazy river, zero entry pool, kids water play area, a separate heated pool for the cooler months, hot tubs, propane grills, a full gym, on site tiki bar, and free gated parking.

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.

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!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Walk/Free Shuttle to Beach, Resort Pool, Huge Home

Sugar Sand Cottage at Destin Pointe

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

Private Pool - Golf Cart - Block to Beach - Destin

#2 4BR HUGE PET Friendly Home Away from Snow!

Private Oasis-Heated Spa Pool-FreeGolfCartTilMar1

Harbor Central Penthouse

Breeze! New. 2 blocks to beach - Sleeps 26 - Pool!
Apartment rentals with a pool

High-End Beachfront Condo w/Breathtaking Gulf View

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

Destin West Villa PH04~ Hot Tub,on Rooftop Terrace

Seascape Ocean View Walk To Beach - Heated Pools

Lovely beach-front condo with free beach setup.

Amazing View Beach Front Condo

Steps from Sand - Fort Walton Beach

Beachside-Top Floor-Pools-Lazy River-Beach Service
Other holiday rentals with a pool

Located on the Water | Near Destin | Downtown FWB

Bay Dreamin' at Hermitage By the Bay

Pool Table, Lazy River & AmazingViews! Destin West

9 Unit Building, Private Pool, Gulf Front View

B210 Pirates Plunder

ChristmasGetaway~PvtBeach~Heatedpool~HotTub~Resort

2 Bedroom Condo on the Beach at Okaloosa Island

Summer is coming Book now Discounts for week stay
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 | $198 SGD | $213 SGD | $280 SGD | $290 SGD | $296 SGD | $367 SGD | $393 SGD | $277 SGD | $245 SGD | $249 SGD | $204 SGD | $196 SGD |
| 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 2,620 holiday rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 55,720 verified reviews to help you choose

Family-friendly holiday rentals
1,900 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
1,570 properties have a dedicated workspace

Wifi availability
2,610 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, Gulfarium Marine Adventure Park and Crab Island
Destinations to explore
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- Beach house rentals Santa Rosa Island
- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- Point Washington State Forest
- Destin Beach
- Aqua Resort
- Crab Island
- Destin Harbor Boardwalk
- WonderWorks Panama City Beach
- Opal Beach
- Pensacola Beach
- Frank Brown Park
- MB Miller County Pier
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulfarium Marine Adventure Park
- The Track - Destin
- Camp Helen State Park
- Gulf Breeze Zoo
- Shipwreck Island Waterpark
- Gulf World Marine Park
- Tarkiln Bayou Preserve State Park
- Henderson Beach State Park
- Pensacola Museum of Art
- Pensacola Bay Center




