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

Total vacation rentals
Explore 2,700 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at $90 per night before taxes and fees

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

Family-friendly vacation rentals
1,990 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
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 vacation rentals include wi-fi 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
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

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.

Relaxing Gulf Front Couple's Retreat*Beach Service
🌊 Beachfront Bliss on Okaloosa Island – Balcony + Free 2 Chairs & Umbrella Welcome to a perfect escape on Okaloosa Island! Wake up to direct Gulf-front views & private balcony w/ emerald waters & sugar-white sand Beautifully updated studio is designed for a relaxing, stress-free beach getaway—to unwind or work remotely with a view We HIGHLY suggest that you purchase Tavel Insurance as we cannot be responsible for travel interruptions, weather or sickness. We adhere to our cancellation policy.

Destin West: Luxurious BAY View BEACH Access CONDO
Enjoy this luxurious 3bd/2ba 1,777 sq ft family friendly condo with a luxury master suite with Jacuzzi; & large balcony overlooking Choctawhatchee Bay. Walk to the dock & eat or sign up for a fishing charter, or rent your own jet skis or pontoon boat and make your way to Destin's Crab Island! Downstairs is the Lazy River, Waterfall pool, 2 heated pools, and 2 heated jet spas. Wristbands are required for this area. Guests can use the sky-bridge to access the beach, restaurants, and entertainment.

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.

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.

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 March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

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.

DestinWest G405 Kid-friendly/oceanview/Lazyriver
[new patio furniture] Destin West Resort Gulfside 405 (2mins to the beach and pool) ~ 1 Bdr + 1 bunkroom with 2 full baths, Sleeps 6 ~ great ocean view ~ free beach service: 2 chairs & 1 umbrella (seasonal: 3/1 - 10/31, 9am-5pm) ~ 1 King Bdr with a private bathroom ~ 1 bunk room (2 twin beds, each with its own TV) with a private bathroom ~ 1 Q pullout sleeper ~ pack n play ~ 4 smart TVs ~ full kitchen stocked with cookware (Keurig and a traditional coffee maker). ~ washer/dryer

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.

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

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
House rentals with a pool

Relaxing Pool Retreat Near Beaches & Destin!

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

Luxury 30A Cottage w/ Private Pool and Golf Cart

Italian villa 200 steps from beach • Free cruise!

Luxurious BeachHouse Pickeball+HeatedPool

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

Destin Pointe | Private Pool + Hot Tub | 2 Beaches

5 Min Walk to Private Beach | Luxury Remodel
Condo rentals with a pool

Waterscape 4th Flr 1 Bedroom w Bunks on the beach

115+ Five-Star Reviews | Renovated Gulf View Condo

Blu 100, 2019 Build, Ground Floor, 2 parking spots

Destin West Resort, Lazy River & Free Beach setup

2nd floor beachfront with amazing views

Waterfront end unit: VIEW! pool, pier, and beaches

Waterfront Studio • Santa Rosa Sound • Sunsets

Ocean view condo, Lazy River & Beach, Destin West
Other vacation rentals with a pool

Sandpiper Cove 8140! 500 ft to the Beach!

Luxury Pool/SPA/BEACH, 1BR w/Dol Views, Full KITCN

"SeaGlass" - Oceanfront with expansive balcony.

Dog-Friendly Coastal Getaway • Walk to Beach!

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

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

Newly Remodeled Beachfront w/ View Destin Condo

WaterScape Guest Favorite | Beachfront | Resort
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 | $162 | $183 | $224 | $226 | $270 | $380 | $305 | $215 | $190 | $184 | $165 | $161 |
| Avg. temp | 53°F | 57°F | 62°F | 68°F | 76°F | 82°F | 83°F | 83°F | 80°F | 71°F | 61°F | 55°F |
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- Rentals with pools Okaloosa County
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Pier Park
- Henderson Beach State Park
- Village of Baytowne Wharf
- Seacrest Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Aqua Resort
- Johnson's Beach, Gulf Islands National Seashore
- HarborWalk Village
- Topsail Hill Preserve State Park
- Grayton Beach State Park
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- Shipwreck Island Waterpark
- The Boardwalk on Okaloosa Island
- Morrison Springs
- Pensacola Bay Center
- Destiny East
- Camp Helen State Park
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