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 £67 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.

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Superhost
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.
Apartment in Santa Rosa Island
4.85 out of 5 average rating, 213 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.

Top guest favourite
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.
Apartment in Fort Walton Beach
4.96 out of 5 average rating, 232 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 favourite
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.
Apartment in Santa Rosa Island
4.93 out of 5 average rating, 280 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 favourite
Apartment in Santa Rosa Island
4.98 out of 5 average rating, 130 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!!

Top guest favourite
Apartment in Santa Rosa Island
4.96 out of 5 average rating, 137 reviews

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

Our spacious Penthouse has amazing views on top of the world! Come enjoy our lovely condo with a roof top patio & private hot tub to see all of Okaloosa Island beach & bay for miles. Or have a romantic evening on the roof top patio with a huge hot tub that overlooks beautiful Choctawhatchee Bay. Located on Okaloosa Island at Destin West Beach and Bay Resort, this island connects Destin to Fort Walton Beach. We are on the bayside. We now offer 1 FREE set-up of beach service March 1-Oct.31st.

Top guest favourite
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.
Apartment in Santa Rosa Island
4.97 out of 5 average rating, 114 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.

Top guest favourite
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.
Apartment in Santa Rosa Island
4.98 out of 5 average rating, 118 reviews

Island Princess 618 | Beach Service Included

Relax and unwind in our beautifully renovated beachfront condo on Okaloosa Island. Unit 618 offers breathtaking Gulf views, an oversized private balcony, comfortable beds, a fully equipped kitchen, and a spacious living area perfect for families and couples. Enjoy direct beach access, sugar-white sands, emerald waters, and complimentary beach service (2 chairs + umbrella) March–October. Conveniently located near Fort Walton Beach and Destin.

Top guest favourite
Apartment in Fort Walton Beach
4.97 out of 5 average rating, 108 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

Guest favourite
Apartment in Santa Rosa Island
4.97 out of 5 average rating, 119 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).

Guest favourite
A scenic view of the beach at sunset, with the sun dipping below the horizon. Gentle waves lap against the shore, while silhouettes of people can be seen strolling along the sandy beach. The sky is tinted with soft orange and yellow hues, enhancing the tranquil atmosphere.
Apartment in Santa Rosa Island
4.82 out of 5 average rating, 155 reviews

Keeler Island Princess #508 Okaloosa Island Bchfrt

Escape the average life at the Majestic Island Princess. Reserve your time today at the Keeler Island Princess #508. Every angle in the living area provides a view so irresistible, you won't be able to take your eyes away from the enticing waters. The diamond sand sparkles with the sun's continuous movement in the sky. Each day, you will discover a new focal point and anticipate its return.

Guest favourite
A sweeping view overlooking the beach showcases soft white sand and the Gulf of Mexico's gentle waves. Blue beach umbrellas are set up along the shore, with a designated swimming area visible. In the foreground, a swimming pool is bordered by palm trees and lounge chairs.
Apartment in Santa Rosa Island
4.92 out of 5 average rating, 306 reviews

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.

Top guest favourite
A spacious studio unit features a comfortable bed with light bedding and decorative striped accents. A seating area includes a grey sofa and a small table set, overlooking large glass doors that open to stunning ocean views. A neutral color palette enhances the coastal ambiance.
Apartment in Santa Rosa Island
4.97 out of 5 average rating, 115 reviews

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.

Popular amenities for Santa Rosa Island rentals with a pool

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