
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 $116 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

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

Wifi availability
2,690 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
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

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.

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.

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.

Beachfront condo with views
Door to sand in 2-3 minutes. First floor, one flight of stairs and out the private dune walkover, no elevator wait. Gulf view from your balcony, close enough to hear the surf and watch the summer fireworks. Updated unit, pet free building. Private king bedroom, bunk nook off the hall, sleeper sofa. Six sleep, nobody on the floor. Stewby's, ice cream, and putt putt across the street. 15 minutes down the beach to the pier and Boardwalk. 2 chairs and umbrella included, set up for you Mar-Oct.

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

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!

Okaloosa Island Top Floor 2BR Beach Condo
Welcome to the Islander unit 707, a cozy beachfront condo located on the seventh (top) floor of the Islander Beach Resort on Okaloosa Island. This charming two-beds, two-bathroom unit has everything you need for a comfortable and relaxing stay. Enjoy stunning views of the Gulf of Mexico from the private balcony or take a short stroll to the white sandy beach just steps away.

Gorgeous Gulf Front condo with amazing views!
Your romantic Gulf-front getaway begins here and is a top-rated destination for couples...This recently updated condo offers new furnishings and is tastefully decorated in warm blue-grey and emerald tones - perfect for a seaside vacation. The Gulf views from your private top floor balcony are unparalleled and promise amazing sunsets.

Gulf Views at 5th-Floor Beachside Condo
Welcome to our little piece if paradise. Located in the beautiful Okaloosa Island, this unit is perfect for you family vacation or getaway! The beautiful beaches are just steps away and accessible through a private beach access. Wheelchair friendly. The heated indoor and outdoor pool makes this complex enjoyable any time of year.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

Pool, Golf Cart, Fire Pit, & Walk to Beach

Luxury 30A Cottage w/ Private Pool and Golf Cart

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Relaxing Pool Retreat Near Beaches & Destin!

Italian villa 200 steps from beach • Free cruise!

SUNDESTIN BEACH RESORT 912, BEACHFRONT

Luxurious BeachHouse Pickeball+HeatedPool
Apartment rentals with a pool

Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver

Oceanfront 3 King BR/3BA Condo Steps 2 Sand & Surf

Beachfront Bliss! Gulf Waves at The Palms #201

Ocean view condo, Lazy River & Beach, Destin West

Waterpark Condo with Free Beach Setup & Aqua Pass

2 min walk to Beach/Free Beach Service/Pool

Dog-Friendly Coastal Getaway • Walk to Beach!

"SeaGlass" - Oceanfront with expansive balcony.
Other holiday rentals with a pool

Palm Court Sunset, walk to beach

Newly Remodeled Spotless Beachfront Destin Condo

Gulf Front Corner Penthouse w/ Panoramic Views

Beach Therapy at The Palms - Free Beach Service!

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

Sandbarr - Bayfront home with a Golf Cart!

507 Destin West Gulfside ~ Free Beach Service!

Gulf-Front Escape on Okaloosa Island (Veranda 203)
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 | $209 SGD | $237 SGD | $290 SGD | $291 SGD | $297 SGD | $368 SGD | $394 SGD | $278 SGD | $246 SGD | $238 SGD | $213 SGD | $208 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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- Apartment rentals Santa Rosa Island
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- Rentals with a hot tub Santa Rosa Island
- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Henderson Beach State Park
- Village of Baytowne Wharf
- Frank Brown Park
- Seacrest Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Aqua Resort
- Grayton Beach State Park
- HarborWalk Village
- Gulf Breeze Zoo
- Topsail Hill Preserve State Park
- Pier Park
- Fort Walton Beach Landing
- Shipwreck Island Waterpark
- Jade East Towers
- The Boardwalk on Okaloosa Island
- Camp Helen State Park
- Gulf World Marine Park
- Gulfarium Marine Adventure Park





