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.

%{current} / %{total}1 / 1
Guest favorite
A large, inviting swimming pool features colorful floating lily pads and a rope bridge. Surrounding the pool are palm trees and lounge chairs, with poolside umbrellas providing shade. A colorful bar area is visible in the background, enhancing the resort's family-friendly atmosphere.
Condo in Fort Walton Beach
4.86 out of 5 average rating, 201 reviews

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.

Guest favorite
Condo in Fort Walton Beach
4.95 out of 5 average rating, 146 reviews

Beachside-Top Floor-Pools-Free Bch Svc & Gym

Named as one of the top 10 “Best beaches in the US”. Come to Okaloosa Island for a great relaxing vacation! Surrounded by crystal clear emerald waters and sugar white beaches, this top floor (6) condominium offers spectacular views of the gulf and the night lights of Okaloosa Island with breathtaking sunrises and sunsets over the gulf. This is it...your Best Beach Retreat! Imagine your "toes in the sand" all within a stones throw from your front door. Come, See and Experience it for yourself!

Top guest favorite
A spacious balcony overlooks the sandy beach and shimmering Gulf waters. Two black chairs with armrests are positioned for relaxation, while a welcoming doormat adds a touch of home. The view captures the pristine shoreline and beach service setups along the coast.
Condo in Fort Walton Beach
4.98 out of 5 average rating, 120 reviews

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!!

Superhost
Condo in Fort Walton Beach
4.8 out of 5 average rating, 154 reviews

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.

Top guest favorite
A serene twilight view captures the sky filled with clouds reflecting subtle shades of orange and blue. The marina lights twinkle along the water's edge, while the horizon highlights an array of colors as day transitions into night.
Condo in Fort Walton Beach
4.97 out of 5 average rating, 193 reviews

Waterfront Studio • Santa Rosa Sound • Sunsets

Enjoy breathtaking views of the Santa Rosa Sound and marina from your private top-floor balcony in this waterfront studio. Whether you're sipping coffee at sunrise or watching vibrant sunsets each evening, this spot delivers unforgettable costal charm in a quiet, peaceful setting. Perfect for couples or solo travelers, the studio features a full bath with tile shower, well-equipped kitchenette and sparkling pool. Gulf beaches are a just a short drive away. Free parking and easy self check-in.

Guest favorite
The living area features a light-colored sofa and a wooden coffee table, with a flat-screen TV on an entertainment unit. Natural light enters through sliding glass doors leading to a balcony with outdoor dining furniture, providing views of the bay.
Condo in Fort Walton Beach
4.91 out of 5 average rating, 106 reviews

Destin West, Bayside, 2 BR+ Bunk Room, sleeps 8

GREAT VIEWS!!! Sandpiper unit 502 has 2 bedrooms, two baths, and a private bunk-bedroom, so its really a 3 BR...sleeps 8. It is furnished with a new sofa sleeper and matching couch in family room. All of this is designer furnished condo accommodates up to eight people to sleep. The interior of the unit reflects a classic, high-end feeling. Walking distance to many restaurants and activities. My place is close to restaurants and dining, the beach is 5 minute away over elevated walkway, .

Top guest favorite
The living area features large glass doors allowing natural light and unobstructed Gulf views. It includes a comfortable seating arrangement with a stylish couch, a dining table for four, and a flat-screen TV, all situated on upgraded flooring.
Condo in Destin
4.96 out of 5 average rating, 163 reviews

Upgraded 7th Flr Pelican Beach Resort-on the beach

Beautiful 7th-floor beachfront condo at Pelican Beach Resort with sweeping, unobstructed Gulf views from the living room, kitchen, dining area, and private balcony. Guests love the coastal charm and wood-look tile flooring throughout. Watch dolphins from the balcony in the morning and enjoy stunning sunsets in the evening. Features a fully updated kitchen, stylish furnishings, smart TVs with Netflix, high-speed Wi-Fi, and beach chairs with umbrella stored in the unit. A true guest favorite!

Guest favorite
A scenic view of the Gulf of Mexico is captured from a private balcony. The image showcases soft waves and sandy beachfront lined with umbrellas and beach chairs. Tropical palm trees frame the foreground, while a well-maintained pool area is visible below.
Condo in Fort Walton Beach
4.81 out of 5 average rating, 139 reviews

Cheery Condo-Free Beach Service-Direct Ocean View!

Let your cares literally drift away in this relaxing, kid-friendly, beautifully decorated condo with a King bed w/bath + twin/twin bunk area w/bath - Queen LR sleeper sofa. Enjoy stunning views of the Gulf of Mexico and pool area from your private balcony. We invite you to enjoy your special vacation at this perfect Emerald Coast paradise. Free beach service (2 chairs and umbrella) is INCLUDED! (March 1-Oct 31). *Note - Okaloosa County Tourist Tax of 6% will be applied to this booking.

Top guest favorite
A living room features a spacious white sofa and a wooden coffee table, with a decorative bowl in its center. Floor-to-ceiling sliding glass doors reveal a balcony with views of the Gulf. A large Smart TV is mounted on the opposite wall.
Condo in Miramar Beach
4.98 out of 5 average rating, 140 reviews

Majestic Sun B613*Remodeled* Gulf Views*Beach Gear

☆☆ WHAT TO LOVE ABOUT THIS HOME: ☆☆ ✹ Amazing GULF VIEWS from living room and master bedroom ✹ REMODELED - New Flooring, walk in shower ✹ Large balcony space for relaxing and dining ✹ 1 King bed + 1 Queen bed + 1 Queen sleeper sofa ✹ Pools, hot tubs, fitness center, tennis courts, golf course ✹ Numerous restaurants within walking distance (Cabana Cafe next door!) ✹ BEACH GEAR Provided - Wagon, backpack chairs, umbrella, towels, & toys ✹ Gated Community with security ✹ 65" Smart TV

Guest favorite
A clear view of the beach and ocean can be seen from the balcony, with lounge chairs and umbrellas set up along the shoreline. A spacious pool area, filled with sun loungers and palm trees, is visible below, complementing the scenic ocean backdrop.
Condo in Fort Walton Beach
4.95 out of 5 average rating, 110 reviews

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

Top guest favorite
A well-appointed studio condo features a modern kitchen with a stainless steel refrigerator and ample counter space. A round dining table with four chairs sits beside a cozy sitting area that includes a sleeper sofa and a colorful quilted bed, all bathed in soft, natural light.
Condo in Destin
4.93 out of 5 average rating, 263 reviews

3 Min Walk to the Beach, Beach Svc, Sandpiper Cove

***Beach service at our private beach for 2 included**** A beautifully decorated studio condo that sleeps 4 comfortably. It includes a queen size bed and queen size sleeper sofa with a memory foam mattress. Not to mention a breakfast bar and 55” TV with surround sound. You can stand on the back deck and see views of the sugary white sand beaches that are right across the street from our place. Beach service at our private beach for 2 included from March-October.

Guest favorite
A balcony offers a stunning view of the Gulf, with the sun reflecting off the water. A small round table with two chairs is situated on the balcony, alongside a cooler and beach gear, enhancing the coastal atmosphere.
Condo in Destin
4.91 out of 5 average rating, 203 reviews

19th Floor Pelican Beachfront with Ocean View

Welcome to your family vacation home at Pelican Beach Resort, Destin; with all the conveniences of a direct beach vacation rental. Your beachfront condo is on 19th floor, optimizes your endless gulf view with the ease of beach access. With our upgrades, we want our guests to feel like they are staying on their beach home. Your home is in the heart of Destin and just a short distance from The Harbor Walk, directly across the street from The Big Kahuna Water Park.

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ566ﺩ.ﺇ606ﺩ.ﺇ797ﺩ.ﺇ826ﺩ.ﺇ845ﺩ.ﺇ1,047ﺩ.ﺇ1,120ﺩ.ﺇ790ﺩ.ﺇ698ﺩ.ﺇ676ﺩ.ﺇ606ﺩ.ﺇ591
Avg. temp12°C14°C17°C20°C24°C28°C29°C28°C27°C22°C16°C13°C

Quick stats about vacation rentals with a pool in Santa Rosa Island

  • Total vacation rentals

    Explore 2,620 vacation rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 55,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,900 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,570 properties have a dedicated workspace

  • Wi-Fi availability

    2,610 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

Destinations to explore