
Vacation rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
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.

The Merry Whale on The Emerald Coast
Newly updated 1 bedroom/ 2 bath condo with built in bunkbeds. Located beach side on the 19th floor with breathtaking panoramic views of the emerald waters and pristine white sand beaches The Gulf of Mexico. Fully stocked kitchen with new granite countertops and slate appliances. Reliable fast high speed internet throughout. Resort amenities include a large pool and hot tub, a beachside tiki bar serving frozen drinks and beer. A fabulous cafe that serves hot breakfast, pizza, sandwiches & salads.

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

Amazing Top-Floor Condo, Free Beach Service!
Decorated in soothing designer colors with a coastal feel, the unit has 2 bedrooms with comfortable king size beds, flat screen TVs and private bathrooms; two bunk beds in a hallway alcove; 2.5 bathroom, and open concept full size kitchen with all new full size stainless steel appliances, dining area and living room with a sleeper sofa. The unit sleeps eight. Plus, you'll have access to all of Waterscape Resort's fabulous amenities! Complimentary beach service with 2 beach chairs and umbrella.

Waterfront two bedrooms apartment
Cozy waterfront two-bedroom apartment! Only two minutes away from the ocean! Accommodates up to 6 people - 1 king bed, 1 queen bed and sofabed. Fully equipped kitchen, washer and dryer in the unit. For your convenience, there is one parking spot available in the building parking lot, any additional parking is by the building. There are inside and outside swimming pools (one is heated), gym and several barbeque stations. Located in the family friendly community, quite time is from 10 pm to 8 am.

Direct Beach FRONT-Amazing Views-Lazy River-Beach
☀️ Direct Gulf-Front Condo | Best Views & Resort Perks! 🌊 Stay in our 4th-floor corner condo at family-friendly Destin West Beach & Bay Resort, w/ unbeatable 180° Gulf views from a wrap-around balcony! 1 of only 10 true beachfront condos, you'll enjoy unobstructed ocean views plus a 700-ft Lazy River, a 5,000 sq. ft. pool, 2 seasonally heated pools, hot tubs, a zero entry pool, & more! Best of all, we offer 1 free beach service setup with our condo thru Oct. 31st. Must be 25 or older to stay.

Beach Side- 2Br 2Ba 3bed | POOLS- GEM-BEACH!
Walk to the Beach at Sunset or Sunrise Every Day! 2 pools, indoor pool & outdoor pool next to the White Sand Beach Access, BBQ Area, elevator & fitness room amenity. Come and enjoy Fun & Sun at our condo by the beach! Gorgeous 2 Br 2 Ba condo is an amazingly nice & quiet like open air community on 2nd floor/elevator, balcony view looks over the neighboring county beach access and down the shoreline PERFECT for those summer fun & sunsets! Morning /Afternoon Walk on the 2 miles Santa Rosa Blvd.

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.

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.

Lovely beach-front condo with free beach setup.
As soon as you enter our 3rd floor beachfront condo, you will leave all your cares behind and unwind while enjoying a direct view of the Gulf of Mexico. You can walk to the beach straight out of the building, no need to cross any roads. Many updates done in March 2021: brand new queen size sleeper sofa bed, brand new stainless steel refrigerator, range, dishwasher and microwave, brand new furniture, new paint, new flooring, and brand new TV's. We have Netflix and high speed WiFi.

Luxury 30A Cottage w/ Private Pool and Golf Cart
A NEWLY BUILT LUXURY COTTAGE DESIGN BEACH HOUSE WITH PRIVATE/HEATED POOL* AND GOLF CART in the heart of Santa Rosa Beach off 30A. This beach house is nestled among the trees yet only minutes away from the white sandy beaches. Bask in the sun by day and wind down and relax in the outdoor areas surrounded by a peaceful wooded area by night. It is like stepping out of one world directly into another. Come and Relax and enjoy the peace and tranquility of this cozy retreat.

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

Private POOL- Gated beach access-grill-backyard

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

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

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Emerald Gulf Bliss | 5-Min Walk ·Pool ·Yard ·Pets

30A 5 Min Walk to Beach/View/Private Pool/Family

Harbor Central Penthouse

Relaxing Pool Retreat Near Beaches & Destin!
Condo rentals with a pool

Sandy Cheeks/Okaloosa Island

Okaloosa Island Condo. (13 ).Small pet/pool/grill

Direct Gulf Views, Private Pool, Sleeps 4

Just a few steps to the white sand beach

Sea Oats*Beachfront View!2Bdr/2Bath, Sleeps 6

BEACHFRONT!! Ground floor condo w/ 2 bedroom&2bath

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

308 Gulf Views • SUPER Savings Book June 13th
Other vacation rentals with a pool

Emerald Coast Escape

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

Nautilus 1402 Gulf Front 1 Bedroom 4th Floor Free

Clean & Luxurious Beachfront ~ 7 Pools+HotTubs+Gym

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

Gulf Dunes 506-Hello Sunshine | GulfFront+2 Pools

Beach Therapy at The Palms - Free Beach Service!

Aloft at Pirates Bay
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$33,880 GYD | G$38,272 GYD | G$46,847 GYD | G$47,056 GYD | G$48,102 GYD | G$59,604 GYD | G$63,787 GYD | G$44,965 GYD | G$39,736 GYD | G$38,481 GYD | G$34,508 GYD | G$33,671 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 |
Quick stats about vacation rentals with a pool in Santa Rosa Island

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

Nightly prices starting at
Santa Rosa Island vacation rentals start at G$14,640 GYD per night before taxes and fees

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

Family-friendly vacation rentals
2,020 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

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

Wi-Fi availability
2,660 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
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Aqua Resort
- Seacrest Beach
- Opal Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- HarborWalk Village
- Fort Walton Beach Landing
- Henderson Beach State Park
- The Boardwalk on Okaloosa Island
- Shipwreck Island Waterpark
- Topsail Hill Preserve State Park
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Pier Park
- Gulf World Marine Park
- Jade East Towers





