Holiday rentals with a pool in Santa Rosa Island

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.

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!

4.95 out of 5 average rating, 146 reviews

Beachside-Top Floor-Pools-Free Bch Svc & Gym

Named as one of the top 10 “Best beaches in the US”. Come to Okaloosa Island for a great relaxing vacation! Surrounded by crystal clear emerald waters and sugar white beaches, this top floor (6) condominium offers spectacular views of the gulf and the night lights of Okaloosa Island with breathtaking sunrises and sunsets over the gulf. This is it...your Best Beach Retreat! Imagine your "toes in the sand" all within a stones throw from your front door. Come, See and Experience it for yourself!

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.

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.

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.

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.

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.

4.82 out of 5 average rating, 149 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!

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.

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.

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.

A table set for refreshments showcases a spread of crackers, cheese, fruits, and chilled water with lemon. In the background, the emerald waters of the Gulf are visible, with beach umbrellas dotting the shoreline under a partly cloudy sky.

4.99 out of 5 average rating, 107 reviews

Spacious, elegant, beachfront, w/office

* Huge oceanfront lanai * Free beach service April 1-Oct 31 *Adult/Kiddie pool; tennis *Private office space in the condo *High chair/pack-n-play *Huge 1453 sq ft *Fully stocked kitchen incl. air fryer *Near Destin but WAY less crowded *South facing for sunrise & sunset (seasonal) & sometimes dolphins! *Open the door to your private lanai for REAL white noise of the ocean waves

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.

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.

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.

4.95 out of 5 average rating, 171 reviews

Waterscape A207/Free BCH SVC/2Kings/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

Superhost

4.77 out of 5 average rating, 120 reviews

Kid-friendly! Lazy River~Skywalk over to beach!

This is a beautiful one bedroom condo plus bunk area located on Bayside of Destin West! The unit comes equipped with a beach cart to make the short walk to the beach even easier! You will love the location of this unit! Freshly painted, with beautifully decor, plus beach towels (2) - you will feel right at home at our 'Salty sandpiper'. With a fully stocked kitchen, washer and dryer, and a lazy river pool - this condo is the perfect place for your beach getaway!

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.

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

Popular amenities for Santa Rosa Island rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.96 out of 5 average rating, 125 reviews

Sugar Sand Cottage at Destin Pointe

A hot tub with bubbling water is positioned in the foreground, offering a relaxing space for guests. In the background, a swimming pool is surrounded by lush palm trees and outdoor furniture, under a bright blue sky with scattered clouds.

4.95 out of 5 average rating, 101 reviews

Heated Pool & HotTub+ Golf Cart+Beach Service

4.92 out of 5 average rating, 109 reviews

Waterview Villa-Steps to the Sand-Pool-King Bed

The exterior of a two-story coastal home is presented, featuring a white façade with ample blue accents. A covered porch extends along the front, showcasing large windows and doors. Lush green landscaping and a picket fence enhance the inviting entrance, complemented by an American flag gently waving.

5 out of 5 average rating, 103 reviews

Private Pool - Golf Cart - Block to Beach - Destin

4.91 out of 5 average rating, 137 reviews

The outdoor area features a spacious swimming pool surrounded by a concrete deck. Brightly colored lounge chairs are positioned at one end. Tall trees provide a natural backdrop, while a stone fireplace is visible in the corner, indicating a cozy gathering spot.

Home in Mary Esther

Emerald Oasis: Hot Tub + Sleeps 18 + Pool+ Grill

A panoramic view showcases the serene outdoor space featuring a large pool surrounded by lounge chairs and palm trees. The inviting villa structure is positioned in the background, highlighting its connection to the lush greenery and the nearby beach, just a short walk away.

4.88 out of 5 average rating, 121 reviews

Private Oasis-Heated Spa Pool-FreeGolfCartTilMar1

Home in Fort Walton Beach

The outdoor area features a non-heated swimming pool surrounded by a concrete patio. A small table with chairs is positioned nearby, offering a space for relaxation. Lush greenery provides shade, and a seating area with chairs is visible on the lawn.

4.9 out of 5 average rating, 312 reviews

#1 4BR HUGE PET Friendly Home Away from Snow!

4.95 out of 5 average rating, 118 reviews

A two-story white house is depicted with a paver driveway leading to the entrance. A 6-seater golf cart is parked in front, surrounded by green landscaping including palm trees. The home presents a welcoming facade, featuring a covered porch and multiple windows.

Home in Miramar Beach

All you need! Location | Golf Cart | Walk to Beach

Apartment rentals with a pool

4.96 out of 5 average rating, 56 reviews

Bay Dreamin' at Hermitage By the Bay

4.93 out of 5 average rating, 263 reviews

A well-appointed studio condo features a modern kitchen with a stainless steel refrigerator and ample counter space. A round dining table with four chairs sits beside a cozy sitting area that includes a sleeper sofa and a colorful quilted bed, all bathed in soft, natural light.

Apartment in Destin

3 Min Walk to the Beach, Beach Svc, Sandpiper Cove

4.89 out of 5 average rating, 159 reviews

Waterfront Paradise•Snowbird Rates Available

4.85 out of 5 average rating, 203 reviews

Marcel: Best view in Ft. Walton Beach/Destin

A panoramic view captures the lagoon-style pool surrounded by lush greenery and palm trees. The sparkling water reflects the vibrant blue sky, showcasing the serene waterfront and distant boats that can be seen along the coastline.

4.77 out of 5 average rating, 261 reviews

Waterfront Condo *w/pool access*

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.

4.95 out of 5 average rating, 109 reviews

Free Chair Service-Beachfront 4th Floor

The image displays a direct view from the private balcony overlooking the sandy beach and the Gulf of Mexico. The soft white sand stretches into the distance, meeting the calm waters with varying shades of blue and green under a clear sky.

4.88 out of 5 average rating, 182 reviews

Relaxing Gulf Front Couple's Retreat*Beach Service

An open living area is furnished with a comfortable gray sofa and a coffee table made of wood. A flat-screen TV is mounted on the wall opposite a sliding glass door that leads to a balcony with a view of the Gulf. Soft lighting and coastal decor enhance the inviting space.

5 out of 5 average rating, 15 reviews

Beachfront - Amazing View - Newly Remodeled!

Other holiday rentals with a pool

5 out of 5 average rating, 8 reviews

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury

A private beachfront balcony is shown with two turquoise chairs facing the ocean. The sparkling water and sandy beach extend in the background under a clear, blue sky, creating a serene space for relaxation.

4.85 out of 5 average rating, 81 reviews

Direct Beach Views, Pool, Chairs & Balcony Bliss

A small outdoor table is set with two cups and a plate of fresh fruit and a bagel. In the background, a view of the Gulf of Mexico is visible, with tall grass and a palm tree framing the beachfront setting.

4.96 out of 5 average rating, 78 reviews

9 Unit Building, Private Pool, Gulf Front View

Superhost

A modern living area features a spacious sectional sofa and a wooden dining table. Large glass doors provide access to a balcony with beach views. Natural light floods the space, complemented by decorative lighting and a large clock on the wall.

Flat in Miramar Beach

4.78 out of 5 average rating, 65 reviews

Stunning Ocean Vibes Retreat

A view from the balcony reveals a boardwalk leading to the beach, flanked by palm trees. The ocean is visible in the distance under a clear blue sky. Multiple parked cars are situated in the foreground, with a beachside building peeking through.

4.98 out of 5 average rating, 65 reviews

2 Bedroom Condo on the Beach at Okaloosa Island

5 out of 5 average rating, 10 reviews

Sunset Dreamin! Come join us for some R&R

5 out of 5 average rating, 17 reviews

Waterfront 1-Bdr Private Balcony

An aerial view of a resort-style condominium showcases a large swimming pool surrounded by palm trees and lounge chairs. The multi-story building, featuring multiple balconies, is situated near the water, with the coastline visible in the distance under a clear blue sky.