Some info has been automatically translated. Show original language

Vacation 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 favorite
A light-filled living area features a comfortable sofa facing large glass doors that open to a private balcony, revealing sweeping views of the Gulf of Mexico. A wooden dining table is set, accompanied by modern white chairs. A unique chandelier hangs above, adding contemporary style.
Condo in Destin
4.95 out of 5 average rating, 222 reviews

The Merry Whale on The Emerald Coast

Newly updated 1 bedroom/ 2 bath condo with built in bunkbeds. Located beach side on the 19th floor with breathtaking panoramic views of the emerald waters and pristine white sand beaches The Gulf of Mexico. Fully stocked kitchen with new granite countertops and slate appliances. Reliable fast high speed internet throughout. Resort amenities include a large pool and hot tub, a beachside tiki bar serving frozen drinks and beer. A fabulous cafe that serves hot breakfast, pizza, sandwiches & salads.

Top guest favorite
An aerial view captures the beachfront property with the sparkling Gulf waters in the background. The surrounding area includes manicured landscapes and beach access points, emphasizing the close proximity to nature and leisure activities.
Condo in Miramar Beach
4.98 out of 5 average rating, 111 reviews

Gulf Views! • Bikes• Garage • Pool • Gated Beach

Welcome to Serenity, A Wave From It All! at Beach Resort in Miramar Beach. Make memories while enjoying glistening views of the Gulf from this stylish 4th floor condo. Located directly across the street from the white sand beaches and Emerald Green shore line of Destin and perfectly situated near beach-front restaurants, world class shopping, stunning golf courses and endless entertainment options. 20-min to Crab Island and the Harborwalk. 15-min to SanDestin/Baytowne Wharf 40-min to airport

Top guest favorite
A bright living area showcases large sliding glass doors that open to a private balcony with ocean views. Comfortable seating is arranged around a coffee table, and decorative elements include a large TV and art pieces depicting the beach, enhancing the coastal ambiance.
Vacation home in Destin
5 out of 5 average rating, 128 reviews

1004 Oceanfront Pelican Beach: Fab Loc Pools/HTubs

1 Bed 2 Bath (Sleeps 6) NO PETS! Non-Negotiable rates. Location! Easy access to attractions! Direct access on the beach without having to cross the street. Pelican Beach Resort 1004 is a newly renovated 1-bedroom condo with stunning Gulf of Mexico views from your private balcony, an open-concept living area, and comfortable sleeping accommodations for up to 6 guests The fully equipped kitchen is designed with a bar that overlooks the living area for entertaining or enjoying a casual meal.

Guest favorite
A balcony table set for two overlooks the serene Choctawhatchee Bay. A bottle of wine is paired with two glasses, inviting relaxation. The expansive water view stretches towards the horizon under a clear blue sky.
Condo in Fort Walton Beach
4.82 out of 5 average rating, 101 reviews

Destin West Penthouse Bay, Roof Top terrace

This fresh looking/newly remodeled Sandpiper PENTHOUSE Condo offers the best of two worlds. It offers breath taking, direct-shot views of the pristine Choctawhatchee Bay , Lazy River and Zero entry & seasonally heated Water Fall pool. The Hot tubs, New Marina and BBQ pits are right below your two balconies. This is a 1 Bedroom with Bunk Room and 2 baths Penthouse condo on the Bay side of Destin West. The views from the roof-top floor blow away the condos on the lower floors. On site Marina!

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, 193 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.

Guest favorite
A sandy beach is visible, leading down to calm turquoise waters under a partly cloudy sky. Rows of colorful umbrellas provide shade for beachgoers, with beach chairs positioned along the shoreline. The scene captures a tranquil coastal atmosphere, ideal for relaxation.
Condo in Fort Walton Beach
4.82 out of 5 average rating, 150 reviews

Steps from Sand - Fort Walton Beach

Welcome to the Nautilus on Okaloosa Island! Enjoy an ocean view from this 2nd floor balcony where you are only steps away from sugar white sand beaches. This two bedroom, two bath condo is the perfect place for your beach vacation. The unit has everything you need, including a washer and dryer. Enjoy the nearby restaurants, shopping and heated pool. This destination will not disappoint! On-site amenities included: Heated pool Private beach access Complimentary Parking BBQ Grills And more!

Guest favorite
A large, mickey-shaped pool is surrounded by lounge chairs and tropical landscaping. In the background, the waterway can be seen, framed by palm trees and extending toward the horizon under a clear blue sky.
Condo in Fort Walton Beach
4.9 out of 5 average rating, 440 reviews

Relaxing Soundside Condo - WataView!

Vacation or work at our comfortable waterfront kitchenette studio in the heart of Fort Walton Beach. The sugar white sand beaches are just a short drive away, and adventure awaits right at your doorstep on Santa Rosa Sound. Includes pool and marina! Boat slip (28 Ft) available! The unit has a queen bed and futon that lays down to a full size bed. It's very comfortable for small groups. We are real owner-hosts and strive to keep our unit spotless and well supplied for our cherished guests.

Guest favorite
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.
Condo in Fort Walton Beach
4.81 out of 5 average rating, 139 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 favorite
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, 126 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.

Top guest favorite
Condo in Fort Walton Beach
4.97 out of 5 average rating, 101 reviews

Seas the View - Island Luxury

NEW Porcelain Tile flooring throughout entire unit! Welcome to Gulf Dunes 105 on Okaloosa Island: - GULF-FRONT & BEACHFRONT - balcony GULF view - Free Beach Service (Mar - Oct) LOW density beach - Sleeps 6: 1 Bedroom: King Bed, Hallway Bunk, Sleeper Sofa - Heated pool 84-86 degrees (Nov-March) The perfect island getaway, for couples and small families, on the emerald waters and white sugar sands of Okaloosa Island. From dusk till dawn, experience the island’s breathtaking beach.

Guest favorite
The image captures a sprawling resort pool area lined with palm trees, inviting lounge chairs, and winding waterways. A mix of tranquil pools is observed, with gentle steps leading into the water and vibrant blue shades reflecting the clear skies.
Condo in Fort Walton Beach
4.87 out of 5 average rating, 122 reviews

Waterscape 5th Flr -Closest 1 Bedroom to the beach

Enjoy the best courtyard and ocean views from this 5th-floor 1BR condo, the closest 1-bedroom unit to the beach at Waterscape Resort. The master bedroom features a king bed and en-suite bath. Kids love the bunk beds with TVs. The unit also includes a sofa bed, stainless steel appliances, in-unit washer/dryer, and beach chairs with umbrella stored in the unit. Guests return year after year for the views, comfort, and resort amenities like pools, waterfall, and lazy river.

Guest favorite
The living area features soft blue walls and large windows providing natural light. A comfortable sofa is complemented by decorative pillows, while a wooden coffee table creates a focal point. A flat-screen TV and light blue curtains enhance the serene atmosphere.
Condo in Fort Walton Beach
4.95 out of 5 average rating, 171 reviews

Waterscape A207/Free BCH SVC/2 Kings/75' TV

Waterscape Resort A207 (just steps to the beach & pools) ~ Ocean view from kitchen/Master BRs/living room/patio ~ FREE beach service (2 CHRs+umbrella) during 3/1-10/31 ~ 2 King BRs with their own en suite + 1 half bath in the living area ~ One bunk room with a DOOR for privacy (two twin beds) ~ Q pullout sleeper ~ Pack 'n Play ~ Highchair ~ 4 smart TVs (1x75’’, 2x50’’, and 1x32’’) ~ Upgraded appliances & quartzite countertops ~ Tiles throughout ~ Washer/dryer in unit

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,177 GYDG$34,475 GYDG$45,340 GYDG$47,012 GYDG$48,057 GYDG$59,549 GYDG$63,727 GYDG$44,923 GYDG$39,699 GYDG$40,326 GYDG$33,013 GYDG$31,759 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 2,620 vacation rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island vacation rentals start at G$8,358 GYD per night before taxes and fees

  • Verified guest reviews

    Over 55,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,900 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,570 properties have a dedicated workspace

  • Wi-Fi availability

    2,610 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