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$14,619 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
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 Santa Rosa Island
4.86 out of 5 average rating, 211 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 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, 231 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, 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 favorite
Condo in Santa Rosa Island
4.98 out of 5 average rating, 129 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 favorite
Condo 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 favorite
A gentle shoreline is framed by soft white sand and vibrant green umbrellas providing shade. The emerald waters of the Gulf of Mexico create a calming contrast against the beach. A wooden walkway leads to the water, bordered by lush coastal vegetation.
Condo in Santa Rosa Island
4.91 out of 5 average rating, 215 reviews

Destin West Villa #V502 Beach Vacation Awaits

Newly updated beach-side 5th floor unit. Renovated bathroom with a large walk in shower. It has one of the best views in the Florida panhandle. A 180 degree view of the emerald waters of the Gulf of Mexico, the Okaloosa Island sand dunes, Destin and Choctawhatchee Bay. Your unit is Gulfside. You are steps away from the white sandy beach, 7 different pools and many restaurants and fun activities to walk to. Relax in the lazy river pool, sunbathe at the beach or spend your day being adventurous.

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, 110 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 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 Santa Rosa Island
4.94 out of 5 average rating, 126 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

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
4.8 out of 5 average rating, 117 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.

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
4.95 out of 5 average rating, 146 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.

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, 214 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, 105 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

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$33,832 GYDG$38,218 GYDG$46,781 GYDG$46,989 GYDG$48,034 GYDG$59,520 GYDG$63,697 GYDG$44,901 GYDG$39,680 GYDG$38,427 GYDG$34,459 GYDG$33,624 GYD
Avg. temp12°C14°C17°C20°C24°C28°C29°C28°C27°C22°C16°C13°C

Destinations to explore