
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.

Beach Penthouse on Okaloosa Island in FWB, FL
Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

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

Beachfront Bliss! Gulf Waves at The Palms #201
Nestled on shimmering Gulf shores, The Palms #201 invites you to unwind with jaw-dropping oceanfront views. This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat. Steps from the water, this guest favorite blends relaxation and rejuvenation for a home-away-from-home feel. From March through October, we provide complimentary beach service with two chairs and umbrella—a $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

Florida...Paradise Island Getaway!
Distinctive ORANGE ADOBE ROOF LINE & beautiful Spanish architecture; Spectacular tropical/ocean view scenery & MAXIMUM PRIVACY, situated on a tropical barrier island, best describes this very spacious 2 Bdr 2 Bth END UNIT w/ NO CROWDS. Miles of PRIVATE isolated beach front EXCLUSIVE ONLY to this resort complex. The closest place to Heaven on earth! From wherever & for however long you travel to this tropical island oasis: "When you come to the end of the road...you'll find paradise!" Luke 23:43

1203 Oceanfront Pelican Beach: Pools/HTubs Fab Loc
NO PETS PERMITTED. PRIMARY GUEST MUST BE 25+ TO BOOK. Indulge in a refined coastal escape at Pelican Beach Resort 1203—an elegantly renovated 1‑bedroom, 2‑bath BEACHFRONT retreat offering breathtaking Gulf of Mexico views and DIRECT, effortless access to Destin’s sugar‑white sands. Perched on the 12th floor, this beautifully appointed residence blends contemporary comfort with resort‑level amenities for UP TO 6 GUESTS, creating an elevated experience for both families & discerning travelers.

Direct Beach FRONT-Amazing Views-Lazy River-Beach
☀️ Direct Gulf-Front Condo | Best Views & Resort Perks! 🌊 Stay in our 4th-floor corner condo at family-friendly Destin West Beach & Bay Resort, w/ unbeatable 180° Gulf views from a wrap-around balcony! 1 of only 10 true beachfront condos, you'll enjoy unobstructed ocean views plus a 700-ft Lazy River, a 5,000 sq. ft. pool, 2 seasonally heated pools, hot tubs, a zero entry pool, & more! Best of all, we offer 1 free beach service setup with our condo thru Oct. 31st. Must be 25 or older to stay.

Amazing- 2BR 2BA 3bed | Pools- GEM-Steps to Beach!
Walk to the Beach at Sunset or Sunrise Every Day! 2 pools, indoor pool & outdoor pool next to the White Sand Beach Access, BBQ Area, elevator & fitness room amenity. Come and enjoy Fun & Sun at our condo by the beach! Gorgeous 2 Br 2 Ba condo is an amazingly nice & quiet like open air community on 2nd floor/elevator, balcony view looks over the neighboring county beach access and down the shoreline PERFECT for those summer fun & sunsets! Morning /Afternoon Walk on the 2 miles Santa Rosa Blvd.

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.

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.

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.

Destin West V409 Cozy Beach Getaway 7Amazing Pools
Newly updated modern beach-side unit. Luxurious renovated bathroom. This Gulfside unit is steps away from the white sandy beach, 7 different pools, and many restaurants. Located on the 4th-floor with one of the best views in the Florida panhandle. A 180-degree view of the emerald waters of the Gulf of Mexico, Choctawhatchee Bay, the Okaloosa Island sand dunes, and the Destin city-scape. Relax in the lazy river pool, sunbathe at the beach, or spend your day being adventurous.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Sugar Sand Cottage at Destin Pointe

6-Seater Golf Cart with Bay, Lake & Golf View Home

Gulf Bliss: 5MinWalkToBeach,Pool+Yard, Shops +Eats

#1 4BR HUGE PET Friendly Home Away from Snow!

Harbor Central Penthouse

Pool Retreat Near Destin Beach

All you need! Location | Golf Cart | Walk to Beach

Sunsail Cottage-Golf Cart Deals-Pool Heat Deals
Apartment rentals with a pool

Discounts for Spring Break

Direct Gulf Front-Lazy River-Pool-Big Balcony VIEW

Clean & Luxurious Beachfront ~ HotTubs+Gym+7 Pools

DestinWest Pelican Bayside, Lazy River, Hot Tub.

CostaVista-Sandestin®: Steps to Beach/Gulf Views!

*NEW*Destin West Heron PH05 ~ Renovated Penthouse

Beach front 2/2 with gulf view.

Sunshine and beach time /Okaloosa Island
Other holiday rentals with a pool

Venus by the Sea – Unit #103

Seaside getaway !

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

Gulf-Front Condo_ Sunrise & Sunset views.

Beach Retreat

Stars & Sea•Overlooking Pool & Sound•Sleeps 4

Okaloosa Island beach condo *with beach service*

New remodel beach front corner unit
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 | £115 | £123 | £162 | £168 | £171 | £212 | £227 | £160 | £142 | £137 | £123 | £120 |
| 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 £30 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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- Rentals with pools Okaloosa County
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Pensacola Beach
- Opal Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Shipwreck Island Waterpark
- Henderson Beach State Park
- The Track - Destin
- Village of Baytowne Wharf
- Gulf World Marine Park
- Topsail Hill Preserve State Park
- HarborWalk Village
- The Boardwalk on Okaloosa Island
- Aqua Resort
- Destiny East
- Johnson Beach




