Holiday rentals with a pool in Santa Rosa Island

Find and book unique homes with a pool on Airbnb

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.

%{current} / %{total}1 / 1
Guest favourite
An aerial view of a beachfront pool area is presented, showing a rectangular pool surrounded by white lounge chairs and shaded areas. The sandy beach is visible just beyond the pool, with a wooden boardwalk leading to the shore.
Apartment in Fort Walton Beach
4.96 out of 5 average rating, 107 reviews

Beach Penthouse on Okaloosa Island in FWB, FL

Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

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
4.95 out of 5 average rating, 216 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 Fort Walton Beach
4.93 out of 5 average rating, 273 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 Fort Walton Beach
4.98 out of 5 average rating, 122 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
A private balcony offers stunning views of the Gulf, featuring two turquoise chairs and a table with two cocktails. The tranquil beach and rolling waves can be seen beyond the white railing, with umbrellas lined up along the shoreline.
Apartment in Fort Walton Beach
4.96 out of 5 average rating, 137 reviews

Star Of The Sea

Welcome to "The Star Of The Sea", Island Princess #312. Enjoy Gulf front views of the aqua blue waters of the Gulf with its sugar sand beaches from our beautifully decorated condo. Private balcony with access from family room and Master Bedroom. Fully stocked kitchen to prepare fabulous meals while taking in the views of the Gulf from the kitchen and dining area. Both master suites boast of comfort and access to private baths with full shower and tub amenities. Flat screen TV's in every room.

Top guest favourite
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.
Apartment in Fort Walton Beach
4.97 out of 5 average rating, 198 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 favourite
The image captures an expansive view of the tranquil Gulf of Mexico. Gentle waves roll onto a sandy beach, while a clear blue sky stretches above, dotted with soft clouds. The horizon blends seamlessly with the serene water, creating a calming seaside atmosphere.
Apartment in Fort Walton Beach
4.94 out of 5 average rating, 207 reviews

Sunshine and beach time /Okaloosa Island

Plan your SUMMER at the BEACH! SNOWBIRDS message us for a monthly rate (Oct-Feb). Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). (USB port outlets, no carpet, stainless appliances, and keyless entry). A one minute walk to the white sand, wifi in the unit, 2 beach chairs, cooler, beach towels, and beach umbrella. Laundry onsite, Tom Thumb next door for items you might need. Everything for a great beach vacation! 683 Nautilus court

Guest favourite
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.
Apartment in Fort Walton Beach
4.9 out of 5 average rating, 209 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 favourite
A light and airy living space features a comfortable seating arrangement with a sectional sofa adorned with patterned throw pillows. A large tufted ottoman sits in the center, complemented by a textured area rug. Soft lighting illuminates the room, enhancing its inviting ambiance.
Apartment in Fort Walton Beach
4.94 out of 5 average rating, 309 reviews

Oceanfront 3 King BR/3BA Condo Steps 2 Sand & Surf

Experience the Gulf in a Newly Remodeled Condo! This family-friendly ground-floor unit offers ultimate convenience. The master bedroom has ocean views, a king bed with a pullout trundle. The second bedroom has a king bed with a trundle, and the third has a King bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

Superhost
A lazy river meanders through lush landscaping, featuring two yellow inflatable tubes floating on the water. Colorful umbrellas provide shade for nearby seating areas. The view reveals the condo buildings in the background, surrounded by palm trees and greenery.
Apartment in Fort Walton Beach
4.77 out of 5 average rating, 163 reviews

Destin West Resort, Lazy River & Free Beach setup

This is a 3-bedroom, 2-bath condo that sleeps 8 people plus a baby. Destin West Resort offers great amenities: 700-foot long Lazy River, 7 Pools (some heated seasonally), 4 Hot tubs, State-of-the-art-Fitness Center and beautiful beach! You also have access to a Marina(bring your boat), picnic areas, water sports/boating rental (next door). The skybridge gives you easy access to both sides of the resort. Walking distance to Adventure Zone, the Gulfarium, the Boardwalk and fishing pier.

Guest favourite
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.
Apartment in Fort Walton Beach
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 favourite
The beach cottage features a welcoming exterior framed by palm trees and tropical foliage. A white picket fence surrounds the property, leading to a spacious porch with multiple steps. The home’s two levels and large windows create an open and airy appearance.
Home in Destin
4.96 out of 5 average rating, 134 reviews

Sugar Sand Cottage at Destin Pointe

This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$197 SGD$211 SGD$277 SGD$287 SGD$294 SGD$364 SGD$389 SGD$274 SGD$242 SGD$235 SGD$211 SGD$205 SGD
Avg. temp12°C14°C17°C20°C24°C28°C29°C28°C27°C22°C16°C13°C

Quick stats about holiday rentals with a pool in Santa Rosa Island

  • Total holiday rentals

    Explore 2,670 holiday rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island holiday rentals start at $89Ā SGD per night before taxes and fees

  • Verified guest reviews

    Over 52,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    2,020 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,560 properties have a dedicated workspace

  • Wifi availability

    2,660 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Okaloosa County
  5. Santa Rosa Island
  6. Rentals with pools