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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Top guest favorite
A scenic view of a resort-style pool surrounded by lush greenery and palm trees. The sparkling water reflects the blue sky, with boats docked nearby. A peaceful atmosphere is suggested by the sun shining brightly over the landscape.
Condo in Fort Walton Beach
5 out of 5 average rating, 115 reviews

Waterfront cozy condo with king bed & resort pool

Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

Top guest favorite
A panoramic view showcases the pristine white sandy beach meeting the azure waters of the Gulf of Mexico. Beach umbrellas line the shore, while a wooden boardwalk leads through lush greenery, providing access to the beach and inviting relaxation in a serene environment.
Condo in Fort Walton Beach
4.9 out of 5 average rating, 245 reviews

NAUTILUS 2608, Sleeps 6, Amazing Views!

Amazing views of the Gulf of Mexico from this 2 bedroom 2 bath condo, sleeps 6. On the 6h floor of the beautiful Nautilus condominium, you will enjoy the wide balcony with incredible views. Fully equipped kitchen, all linen and beach towels included. Beach service from March 1st until Oct 31st (2 chairs & an umbrella) Additional beach chairs and umbrellas in the condo. Heated pool. Many restaurants in the area. Groceries 5 min away. Special rates snowbirds and military on TDY. 25 yr old min.

Top guest favorite
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.
Condo in Fort Walton Beach
4.96 out of 5 average rating, 135 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 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 Fort Walton Beach
4.9 out of 5 average rating, 205 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.

Guest favorite
Condo in Fort Walton Beach
4.88 out of 5 average rating, 574 reviews

Cozy 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 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 Fort Walton Beach
4.96 out of 5 average rating, 102 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.

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, 125 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
A light blue bedroom features a spacious bed dressed in a colorfully patterned quilt. Accents include two bedside tables with lamps, a stylish chair, and a window that allows natural light to brighten the space. Decorative beach-themed art complements the serene atmosphere.
Condo in Fort Walton Beach
4.96 out of 5 average rating, 126 reviews

Retreat by the Sea at Seacrest Condo

Welcome to Retreat by the Sea. This studio is at Seacrest Condominiums located directly on the beach on beautiful Okaloosa Island in Fort Walton Beach six miles from Destin. Relax on the balcony and enjoy the beautiful views of the Gulf and amazing sunrises and sunsets. You have direct access to the beach and all the amenities that the condo has to offer including indoor/outdoor pool, gym and bbq area. This amazing studio also has a kitchenette, mini-refrigerator and private laundry.

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

Perfect View on Santa Rosa Sound with 2 Pools!

Enjoy beautiful blue skies and gorgeous sunsets over the Santa Rosa Sound, while looking out over the marina from your very own private deck! This gorgeous studio unit has one of the best views in the entire 120 room complex! Located in the preferred A building, this Non-Smoking, NO PETS ALLOWED, sparkling clean top floor unit has a beautiful bathroom with full size tile shower and newer plumbing fixtures. Marina slip is not available for rent at this time.

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 Fort Walton Beach
4.83 out of 5 average rating, 199 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
The image showcases a private pool surrounded by a tiled deck and lounge chairs under clear blue skies. The pool offers views of the white sand beach and emerald waters beyond. Palm trees frame the scene, enhancing the beachfront atmosphere.
Condo in Fort Walton Beach
4.98 out of 5 average rating, 100 reviews

Veranda 102 - Direct Beachfront - Gulf Side Pool

Small quaint 9 unit complex. Direct BEACHFRONT on the white sand of Okaloosa Island, FL. Completely remodeled! Breathtaking views of the emerald green waters of the Gulf of Mexico (and dolphins) right from the private patio! Gulf side pool (not heated). Contactless check-in. Walk 1 mile to the Pier & Boardwalk and restaurants. 15 minutes to Ft. Walton Airport. 2 person beach service (1 umbrella & 2 chairs) available 3/1 - 10/31

Top guest favorite
The living area features a spacious seating arrangement with a comfortable sofa and armchair. A large TV is mounted on a wall across from a decorative table. Soft lighting and neutral wall colors contribute to a welcoming ambiance, complemented by greenery from nearby plants.
Condo in Fort Walton Beach
4.88 out of 5 average rating, 131 reviews

"The Golden Sun" condo

"The Golden Sun." A luxury and calm stay in a 4th-floor condo only steps from the beach. Enjoy golden sunsets from the balcony that oversees the beach! Fast wifi with Alex integration(not offered by most condos). This features 1 bed and 1 sofa bed for a 4 person stay. 2 full bathrooms. A nice small kitchen so you can cook! Two TVs with Rokus for streaming. Small community grills for BBQ and a beautiful pool!

Popular amenities for Santa Rosa Island rentals with a pool

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,197 GYDG$34,497 GYDG$45,368 GYDG$47,041 GYDG$48,086 GYDG$59,585 GYDG$63,766 GYDG$44,950 GYDG$39,723 GYDG$40,351 GYDG$33,033 GYDG$31,779 GYD
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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$8,363 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