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$14,658 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.

1 of 1 pages1 / 1
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, 275 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, 126 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 Santa Rosa Island
4.8 out of 5 average rating, 161 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.

Guest favorite
A bright living area features a light grey wall with natural lighting from large windows. Two cozy sofas, one in dark grey and the other in a mixed pattern, offer seating. A white coffee table sits in the center, complemented by a decorative rug and a fan overhead.
Condo in Santa Rosa Island
4.91 out of 5 average rating, 125 reviews

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.

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, 204 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, 104 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 favorite
A spacious living area features a large sofa and a mounted television, along with soft blue lighting that creates a calming atmosphere. The decor includes a decorative wall unit and stylish accents, contributing to a welcoming environment for relaxation.
Condo in Santa Rosa Island
4.96 out of 5 average rating, 112 reviews

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.

Guest favorite
A spacious living area is highlighted by a light-colored sectional sofa and a modern coffee table on a patterned rug. A flat-screen TV is mounted on the textured blue wall, and natural light filters through sheer curtains, enhancing the inviting ambiance.
Condo in Santa Rosa Island
4.96 out of 5 average rating, 139 reviews

2 min walk to Beach/Free Beach Service/Pool

Elevate your vacation experience with a stay at the Beach Hive! Conveniently located less than 2 minutes from the shores of the Gulf. Complimentary beach service (2 beach chairs and 1 umbrella) is available from 3/1-10/31. Escape the crowd & enjoy time at the Beach, lay by the pool or visit all that Okaloosa Island & the Emerald Coast have to offer. Then, return to this modern beach cottage to wind down and relax in style and comfort after a long day.

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, 115 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.

Superhost
An expansive view of the Gulf of Mexico is seen from the balcony, showcasing the sandy beach and turquoise water. The beach is lined with sun loungers, and the resort pool is visible nearby. Lush palm trees and pavilions add to the coastal landscape.
Condo in Santa Rosa Island
4.83 out of 5 average rating, 212 reviews

Islander Resort Okaloosa IsIand Beach Condo

Escape to Okaloosa Island and stay at this cozy studio condominium at the Islander Resort. This 6th-floor unit is perfect for couples or small families looking for a beach getaway. Wake up to stunning views of the Gulf of Mexico from the private balcony, relax on the pristine white sand beach, or take a dip in the Gulf-front pool. Take advantage of the resort's amenities, including a fitness center, shuffleboard, and barbecue grills.

Top guest favorite
Condo in Fort Walton Beach
4.97 out of 5 average rating, 100 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 favorite
A serene view of the beach features soft white sand leading to the emerald waters of the Gulf of Mexico. Beach chairs are arranged in a neat line along the shore, enhancing the tranquil atmosphere. The sky is clear, adding to the inviting coastal scene.
Condo in Santa Rosa Island
4.74 out of 5 average rating, 563 reviews

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

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$33,923 GYDG$38,320 GYDG$46,906 GYDG$47,115 GYDG$48,162 GYDG$59,679 GYDG$63,867 GYDG$45,021 GYDG$39,786 GYDG$38,530 GYDG$34,551 GYDG$33,714 GYD
Avg. temp12°C14°C17°C20°C24°C28°C29°C28°C27°C22°C16°C13°C

Destinations to explore