
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 2,700 holiday rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island holiday rentals start at $158 NZD per night before taxes and fees

Verified guest reviews
Over 57,850 verified reviews to help you choose

Family-friendly holiday rentals
1,990 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
1,580 properties have a dedicated workspace

Wi-Fi availability
2,690 of Santa Rosa Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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
4.96 out of 5 average rating, 238 reviews
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.
4.93 out of 5 average rating, 291 reviews
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.
4.97 out of 5 average rating, 117 reviews
Beach FRONT Condo-Pools-Lazy River-Free Beach Serv
Hello vacationers! You've found the perfect vacation spot! If you are searching for a beautiful, well-furnished condo with gorgeous 180 degree views of sugar white sand and emerald waters, then you have found the right place. This direct beachfront condo is on Okaloosa Island connecting Destin to Ft. Walton. It's a corner condo with sweeping, unobstructed views. Destin West Resort is in walking distance to so many attractions. FREE beach service included til Oct 31! Must be 25 or older to stay.
4.96 out of 5 average rating, 106 reviews
Condo With Serene Panoramic Views of the Gulf
This newly renovated 2nd floor condominium provides panoramic views in a serene atmosphere directly on the Gulf. This unit features a corner wraparound balcony with master and living room views of the emerald waters gently lapping at the white sand beach. This condo is on the quieter, more secluded end of Okaloosa Island just steps to a private beach. Two reserved beach chairs and service are included in your stay (March-October). Relax with the whole family at this peaceful place to stay.
4.98 out of 5 average rating, 120 reviews
Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver
Our spacious Penthouse has amazing views on top of the world! Come enjoy our lovely condo with a roof top patio & private hot tub to see all of Okaloosa Island beach & bay for miles. Or have a romantic evening on the roof top patio with a huge hot tub that overlooks beautiful Choctawhatchee Bay. Located on Okaloosa Island at Destin West Beach and Bay Resort, this island connects Destin to Fort Walton Beach. We are on the bayside. We now offer 1 FREE set-up of beach service March 1-Oct.31st.
4.96 out of 5 average rating, 139 reviews
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.
4.96 out of 5 average rating, 126 reviews
Ocean view condo, Lazy River & Beach, Destin West
From your unit on the Gulf side of the resort, enjoy the spectacular ocean view, award winning lazy river, and many pools in this family friendly Destin West Beach and Bay Resort with private beach. Your unit is a couple blocks from Gulfarium Marine Adventure park, where you can swimming with dolphins. Enjoy the Broadwalk Okaloosa Island with seaside shops, eats, and entertainment within a block. Okaloosa Island fishing pier is within 2 blocks for fishing enthusiasts.
4.88 out of 5 average rating, 145 reviews
2 min walk to Beach/Free Beach Service/Pool
Elevate your vacation experience with a stay at the Beach Hive! Conveniently located less than 2 minutes from the shores of the Gulf. Complimentary beach service (2 beach chairs and 1 umbrella) is available from 3/1-10/31. Escape the crowd & enjoy time at the Beach, lay by the pool or visit all that Okaloosa Island & the Emerald Coast have to offer. Then, return to this modern beach cottage to wind down and relax in style and comfort after a long day.
4.94 out of 5 average rating, 160 reviews
Stars & Sea•Overlooking Pool & Sound•Sleeps 4
Kick back & relax in this calm, newly renovated ground-level condo on the Sound in Ft Walton Beach! ✨ Highlights: • 🌴 Waterfront views & stunning sunsets • 💦 Large resort-style pool • 🏖️ Minutes to beach access • 🍽️ Walk to local restaurants • 🚗 Easy parking & quiet community 🛏️ Queen bed w/Purple® mattress + Queen memory-foam sofa bed ☕ Kitchenette: Fridge • Air fryer/toaster • Microwave • Keurig •7.5 Miles to Destin
4.97 out of 5 average rating, 116 reviews
Direct Gulf Views, Private Pool, Sleeps 4
Wake up to the sound of waves and step onto your private balcony to watch the sun rise and set over the Gulf of Mexico. This beautifully appointed 1-bedroom condo sleeps 4 in a charming 9-unit boutique building — meaning no crowded elevators, no packed pool, and your own quiet slice of the Emerald Coast. Looking for a warm winter escape? Monthly rates and snowbird discounts available November through March.
4.95 out of 5 average rating, 109 reviews
Keeler Island Princess #508 Okaloosa Island Bchfrt
Escape the average life at the Majestic Island Princess. Reserve your time today at the Keeler Island Princess #508. Every angle in the living area provides a view so irresistible, you won't be able to take your eyes away from the enticing waters. The diamond sand sparkles with the sun's continuous movement in the sky. Each day, you will discover a new focal point and anticipate its return.
4.78 out of 5 average rating, 165 reviewsPopular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

#1 4BR HUGE PET Friendly Home Away from Snow!
4.89 out of 5 average rating, 341 reviews
Harbor Central Penthouse
4.89 out of 5 average rating, 159 reviews
Touch of Madagascar-Whole House
4.92 out of 5 average rating, 302 reviews
The Memory Maker - Heated Pool! 4BR Vacation Home
4.9 out of 5 average rating, 115 reviews
Relaxing Pool Retreat Near Beaches & Destin!
4.91 out of 5 average rating, 153 reviews
Luxury 30A Cottage w/ Private Pool and Golf Cart
4.96 out of 5 average rating, 165 reviews
Italian villa 200 steps from beach • Free cruise!
4.96 out of 5 average rating, 182 reviews
5 Min Walk to Private Beach | Luxury Remodel
4.9 out of 5 average rating, 109 reviewsCondo rentals with a pool

Sola Azul | Gulf-Front Luxe + Beach Service
4.94 out of 5 average rating, 140 reviews
Destin West Villa #V502 Beach Vacation Awaits
4.91 out of 5 average rating, 221 reviews
Emerald Waters & Sugar White Sand!
4.75 out of 5 average rating, 582 reviews
Beachfront Condo | Gulf Views | Okaloosa Island
4.93 out of 5 average rating, 135 reviews
Okaloosa Island Beach Condo14/Small Pet/Pool/Grill
4.82 out of 5 average rating, 252 reviews
Beachfront Bliss 2BR/2BA Condo Stunning Ocean View
4.94 out of 5 average rating, 168 reviews
Sunshine and beach time /Okaloosa Island
4.94 out of 5 average rating, 226 reviews
Condo across the street from the gulf
4.84 out of 5 average rating, 456 reviewsOther holiday rentals with a pool

Our Happy Place
4.8 out of 5 average rating, 130 reviews
Beach Side- 2Br 2Ba 3bed | POOLS- GEM-BEACH!
4.92 out of 5 average rating, 135 reviews
Ocean Views at Waterscape Resort!
4.88 out of 5 average rating, 162 reviews
Gorgeous Gulf Front condo with amazing views!
4.97 out of 5 average rating, 121 reviews
Free Chair Service-Beachfront 6th Floor
4.94 out of 5 average rating, 268 reviews
Waterfront end unit: VIEW! pool, pier, and beaches
4.86 out of 5 average rating, 135 reviews
Cheery Condo-Free Beach Service-Direct Ocean View!
4.82 out of 5 average rating, 144 reviews
One Step to the Beach!
4.98 out of 5 average rating, 160 reviewsWhen is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $284 NZD | $320 NZD | $392 NZD | $396 NZD | $473 NZD | $665 NZD | $534 NZD | $377 NZD | $333 NZD | $322 NZD | $289 NZD | $282 NZD |
| 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 |
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Pier Park
- Village of Baytowne Wharf
- Henderson Beach State Park
- Frank Brown Park
- Seacrest Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- HarborWalk Village
- Aqua Resort
- Grayton Beach State Park
- Topsail Hill Preserve State Park
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- Morrison Springs
- Shipwreck Island Waterpark
- Camp Helen State Park
- Gulf World Marine Park
- Gulfarium Marine Adventure Park
- Pensacola Bay Center





