
Holiday rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Santa Rosa Island

Total holiday rentals
Explore 2,670 holiday rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island holiday rentals start at $89Ā SGD per night before taxes and fees

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

Family-friendly holiday rentals
2,020 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

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

Wifi availability
2,660 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 Islandās top spots include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park and Crab Island
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

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.

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 umbrellaāa $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

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.

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.

Sunshine and beach time /Okaloosa Island
Plan your SUMMER at the BEACH! SNOWBIRDS message us for a monthly rate (Oct-Feb). Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). (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

Destin West Villa #V502 Beach Vacation Awaits
Newly updated beach-side 5th floor unit. Renovated bathroom with a large walk in shower. It has one of the best views in the Florida panhandle. A 180 degree view of the emerald waters of the Gulf of Mexico, the Okaloosa Island sand dunes, Destin and Choctawhatchee Bay. Your unit is Gulfside. You are steps away from the white sandy beach, 7 different pools and many restaurants and fun activities to walk to. Relax in the lazy river pool, sunbathe at the beach or spend your day being adventurous.

Oceanfront 3 King BR/3BA Condo Steps 2 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 King bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service MarchāOct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

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.

Cheery Condo-Free Beach Service-Direct Ocean View!
Let your cares literally drift away in this relaxing, kid-friendly, beautifully decorated condo with a King bed w/bath + twin/twin bunk area w/bath - Queen LR sleeper sofa. Enjoy stunning views of the Gulf of Mexico and pool area from your private balcony. We invite you to enjoy your special vacation at this perfect Emerald Coast paradise. Free beach service (2 chairs and umbrella) is INCLUDED! (March 1-Oct 31). *Note - Okaloosa County Tourist Tax of 6% will be applied to this booking.

Sugar Sand Cottage at Destin Pointe
This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

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

Pool - Golf Cart - Block to Beach - Beach Service

Harbor Central Penthouse

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

The Charleston Experience-Free PoolHeat N GolfCart

Pool Retreat Near Destin Beach

Luxurious Private Pool, Beach Walk W/Private Acces

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

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

Clean & Luxurious Beachfront ~ HotTubs+Gym+7 Pools

Veranda 102 - Direct Beachfront - Gulf Side Pool

Destin West V506 - Free Beach Service & Lazy River

Waterscape 3rd Floor 1 Bedroom - on the beach -

One Step to the Beach!

Amazing View Beach Front Condo

Updated 2 Bedroom Steps To Beach
Other holiday rentals with a pool

Sandy Cheeks/Okaloosa Island

Pool Table, Lazy River, & HUGE Patio! Destin West!

Nautilus 1406 -Updated Gulf Front 2 Bed/2 Bath. Fr

Unit #6 Waterfront + Heated Pool and Spa Access

Beach Retreat

WaterScape Now Booking 2026! Beach/resort/pool/spa

Stars & Seaā¢Overlooking Pool & Soundā¢Sleeps 4

Large condo@ Destin West Bayside! Lazy River & Sky
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $197 SGD | $211 SGD | $277 SGD | $287 SGD | $294 SGD | $364 SGD | $389 SGD | $274 SGD | $242 SGD | $235 SGD | $211 SGD | $205 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 |
Destinations to explore
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- Rentals with poolsĀ Okaloosa County
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- Rentals with poolsĀ United States
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Aqua Resort
- Pensacola Beach
- Seacrest Beach
- Opal Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Village of Baytowne Wharf
- Gulf Breeze Zoo
- Henderson Beach State Park
- HarborWalk Village
- Camp Helen State Park
- Shipwreck Island Waterpark
- Gulfarium Marine Adventure Park
- Topsail Hill Preserve State Park
- The Track - Destin
- Gulf World Marine Park
- The Boardwalk on Okaloosa Island
- Pier Park




