Vacation rentals with a pool in Santa Rosa Island

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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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Guest favorite
The living area features a leather couch and a recliner, complemented by a coffee table and a dining table with six chairs. A 55-inch TV is positioned nearby, with views of the bay accessible through sliding glass doors leading to the balcony, enhancing the space's openness.
Condo in Santa Rosa Island
4.93 out of 5 average rating, 131 reviews

Destin West: Luxurious BAY View BEACH Access CONDO

Enjoy this luxurious 3bd/2ba 1,777 sq ft family friendly condo with a luxury master suite with Jacuzzi; & large balcony overlooking Choctawhatchee Bay. Walk to the dock & eat or sign up for a fishing charter, or rent your own jet skis or pontoon boat and make your way to Destin's Crab Island! Downstairs is the Lazy River, Waterfall pool, 2 heated pools, and 2 heated jet spas. Wristbands are required for this area. Guests can use the sky-bridge to access the beach, restaurants, and entertainment.

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.

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, 126 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, 205 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, 105 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 modern living area is showcased with a green sofa and two red armchairs, complemented by light wood flooring. A colorful wall art piece adds vibrancy, while a ceiling fan provides airflow. The open floor plan offers a view into the adjacent dining and kitchen area.
Condo in Santa Rosa Island
4.95 out of 5 average rating, 125 reviews

Free Chair Service-Beachfront 4th Floor

Beautiful fourth-floor balcony views of beachfront, barrier island chain, and sound area! Exceptionally convenient white-sands beach access and gorgeous emerald waters! Enjoy indoor/outdoor pool and on-site gym. This beach condo is not only fantastically located on the quieter end of Okaloosa Island, but also comes with modern, coastal-themed furnishings. Access the Destin and Fort Walton Beach attractions only a few miles down the street. Includes free chairs and umbrella on the beach!

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.

Guest favorite
A round glass table is surrounded by four comfortable chairs on a private balcony. The beach extends below, with soft white sand meeting the calm turquoise water. A pier can be seen in the distance under a clear blue sky.
Condo in Santa Rosa Island
4.96 out of 5 average rating, 124 reviews

Beachfront-Top Floor-West Corner-Free Bch Bch+ Gym

If you’re wanting a vacation where you can sit on your private balcony and enjoy colorful sunsets, sweeping views of the gulf, dolphins playing in emerald green water, seagulls floating by on warm tropical breezes, you need look no further! Welcome to the best of Destin West Gulf Front! This top floor, direct gulf-front condo corner condo offers the perfect vacation spot for that special vacation time. FREE BEACH SERVICE and FITNESS ROOM PROVIDED!

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, 565 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!

Top guest favorite
Condo in Santa Rosa Island
4.96 out of 5 average rating, 113 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$33,872 GYDG$38,263 GYDG$46,836 GYDG$47,045 GYDG$48,090 GYDG$59,590 GYDG$63,772 GYDG$44,954 GYDG$39,727 GYDG$38,472 GYDG$34,500 GYDG$33,663 GYD
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 2,670 vacation rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island vacation rentals start at G$14,636 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

Destinations to explore