
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 G$18,837 GYD 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
ValueLocationBeach

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.
FamilyValueShared spaces

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.
LocationValueComfort

Waterpark Condo with Free Beach Setup & Aqua Pass
Welcome to Waterscape A419! This is a 1292 sqft 2 bedroom, 2 1/2 bath condo with a private bunk room that sleeps 8 people plus a baby. Waterscape is one of the newest and most luxurious direct beachfront resorts in Fort Walton Beach/Destin area. Our Unit is located on the 4th floor with partial beach/ocean views as well as the bay view. The resort has great amenities: 3 amazing swimming pools, a relaxing LAY-Z™ River, 10 gas grills, poolside Tiki Bar, fitness center, and private pristine beach.
ValueFamilyCleanliness

Salt Pool & Spa, Heat Opt, Cali King Bed, Beach 4M
Luxurious home 4 miles to Beach! -Salt Water Pool(heat fee)&Hot tub -Lanai w/seating and 75"TV -Fast WI-FI -Fully equipped kitchen -Dedicated workstation -Coffee bar -Cali King Bed w/ensuite(soaking tub) -Smart TV's & Fans every room -Blackout curtains & Sound machines -Hair Dryer,Steamer -Grill w/propane -Games -Pacn'Play, high chair, baby monitor -4.2 Miles>Beach -9.2 Miles>Crab Island, Destin -4.6 Miles>Eglin AF Base -2.3 Miles>Walmart -0.8 Miles>Publix -7.4 Miles>Airport -2.5 Miles>Hospital
LocationFamilyTV

Waterscape 4th Flr 1 Bedroom w Bunks on the beach
Relax in this beautifully decorated 1BR/2BA condo at Waterscape Resort with 4th-floor views of the courtyard, heated pool, and partial beach/ocean views. The master bedroom features a king bed and en-suite bath. Kids love the bunk beds with TVs. The unit also includes a sofa bed, stainless steel appliances, new flooring, in-unit washer/dryer, and beach chairs with an umbrella. Many repeat guests return for the bunk beds and resort amenities, including three pools, a waterfall, and a lazy river.
LocationFamilyWifi

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.
FamilyValueCheck-in

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.
FamilyValueCleanliness

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
FamilyValueHeating

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.
FamilyValueBeach

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
ValueLocationBackyard

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!
ValueLocationAmenities
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

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

Italian villa 200 steps from beach • Free cruise!
LocationValueBackyard

Luxury 30A Cottage w/ Private Pool and Golf Cart
LocationFamilyLayout

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!
LocationValueAmenities

Destin Pointe | Private Pool + Hot Tub | 2 Beaches
FamilyLocationCheckout

Luxurious BeachHouse Pickeball+HeatedPool
ValueFamilyAccess

Relaxing Pool Retreat Near Beaches & Destin!
ValueFamilyPool

Harbor Central Penthouse
FamilyLocationQuiet
Condo rentals with a pool

Waterfront Studio • Santa Rosa Sound • Sunsets
LocationFamilyGetting around

Beach front 2/2 with gulf view.
LocationFamilyBathroom

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA
LocationFamilyQuiet

2 min walk to Beach/Free Beach Service/Pool
ValueFamilyBathroom

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach
LocationValueGetting around

115+ Five-Star Reviews | Renovated Gulf View Condo
FamilyLocationWifi

DestinWest G405 Kid-friendly/oceanview/Lazyriver
FamilyValueParking

Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver
LocationFamilyLaundry
Other vacation rentals with a pool

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

"SeaGlass" - Oceanfront with expansive balcony.
FamilyValueComfort

Newly Remodeled Beachfront w/ Amazing View Destin
LocationFamilyAccess

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

Clean & Luxurious Beachfront ~ 7 Pools+HotTubs+Gym
ValueFamilyKitchen

Red Fish Blue Fish, Private Pool Home, Dogs OK
ValueFamilyAccuracy

Remodeled 2025! Balcony Beach Service Oceanfront
LocationValueAccess

Dog-Friendly Coastal Getaway • Walk to Beach!
ValueLocationKitchen
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 | G$33,906 GYD | G$38,301 GYD | G$46,883 GYD | G$47,301 GYD | G$56,510 GYD | G$79,533 GYD | G$63,836 GYD | G$44,999 GYD | G$39,766 GYD | G$38,511 GYD | G$34,534 GYD | G$33,697 GYD |
| 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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- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- 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





