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 2,670 vacation rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island vacation rentals start at G$14,644 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

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.

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Top guest favorite
A bright and airy room features large glass sliding doors that open to a private balcony with an ocean view. The space includes a spacious bed adorned with a patterned blue coverlet and a cozy loveseat, with a TV mounted on the wall.
Condo in Fort Walton Beach
4.96 out of 5 average rating, 229 reviews

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

Top guest favorite
A generous balcony features a round table surrounded by four striped chairs, offering ocean views. Two blue lounge chairs are positioned beside the table. The expansive space allows for comfortable relaxation while overlooking the beach and turquoise waters.
Condo in Santa Rosa Island
4.93 out of 5 average rating, 279 reviews

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.

Top guest favorite
Condo in Santa Rosa Island
4.98 out of 5 average rating, 127 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!!

Guest favorite
A serene view of the Gulf waters features soft blue hues blending into the horizon. A long wooden pier extends into the distance, providing a focal point against the clear skies and white sandy beach in the foreground.
Condo in Santa Rosa Island
4.88 out of 5 average rating, 134 reviews

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.

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, 206 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.

Top guest favorite
A spacious and inviting living area showcases a large sectional sofa adorned with blue and white accents. Natural light fills the space through expansive sliding glass doors that offer a view of the Gulf. A ceiling fan provides a refreshing breeze while a coffee table and a patterned armchair complete the seating arrangement.
Condo in Santa Rosa Island
4.97 out of 5 average rating, 107 reviews

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.

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 Santa Rosa Island
4.82 out of 5 average rating, 141 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 spacious living area features a light-colored leather sectional sofa and a circular wooden coffee table, complemented by a plush rug. Large sliding glass doors open to reveal views of the Emerald Coast, with outdoor seating visible on the patio.
Condo in Santa Rosa Island
4.97 out of 5 average rating, 155 reviews

One Step to the Beach!

"One Step to the Beach" Highlights: - Beachfront Condo at Surf Dweller - First Floor - Pull Up to the Front Door and Unload - Free “Platinum” Beach Service: 2 Beach Chairs, Umbrella + Kayak / Paddleboard access (Mar-Oct) - Two Parking Spaces - 1 King Bed - Master Suite - 2 Queen Beds - Second Bedroom - Cable + Streaming - WiFi - Keurig and Drip Coffee Makers - Seasonal Heated Pool - Tennis/Pickleball Courts - Washer and Dryer in the Condo - Pack n' Play - Shopping / Restaurants Nearby

Superhost
A spacious living area is highlighted by a blue bedspread on a queen-sized bed and a dark gray sofa. The kitchen area features white cabinetry and modern appliances. Colorful artwork adorns the walls, creating a light and cheerful atmosphere.
Apartment in Santa Rosa Island
4.81 out of 5 average rating, 115 reviews

Our Happy Place

Pack your bags and head to Our Happy Place. Readily equipped with everything you will need for relaxation, fun or adventure. Our Happy Place is situated on the water where you can sit and watch boats go by, or fish from the shore. Take a dip in the community pool that offers plenty of lounger chairs and tables with umbrellas. Just across the street you will find a boardwalk to stoll down to the white sandy beaches where you can soak up the sun and Gulf of Mexico views.

Top guest favorite
A panoramic view of the beach showcases soft white sands meeting the tranquil turquoise waters of the Gulf. Beach umbrellas and chairs line the shore, with a clear blue sky above enhancing the serene coastal landscape.
Condo in Santa Rosa Island
4.98 out of 5 average rating, 116 reviews

Island Princess 618 | Beach Service Included

Experience the perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

Top guest favorite
Condo in Fort Walton Beach
4.97 out of 5 average rating, 102 reviews

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

Top guest favorite
Condo in Santa Rosa Island
4.96 out of 5 average rating, 114 reviews

Beachfront condo with views

Gulf Dunes 105 – Gulf‑Front & Beachfront Feel the island vibes in this updated 1‑bed, 1.5‑bath condo on Okaloosa Island! Sleeps 6 with king bed, hallway bunks, and sleeper sofa. Enjoy a private balcony with Gulf views, direct beach access, pool, and free beach service (Mar–Oct). Walk to the Boardwalk for food and fun. Perfect for couples and small families. Heated pool 84–85 degrees (Nov–Mar).

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$33,889 GYDG$38,282 GYDG$46,859 GYDG$47,069 GYDG$48,115 GYDG$59,620 GYDG$63,804 GYDG$44,977 GYDG$39,747 GYDG$38,492 GYDG$34,517 GYDG$33,680 GYD
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