
Holiday rentals with a pool in Santa Rosa Island, Florida
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Santa Rosa Island, Florida
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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!!

East Bay Hideaway — A Private Waterfront Escape
Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

La Playa Esmeralda - Panoramic Sunset Views
Welcome to La Playa Esmeralda, a beautifully renovated 2nd floor studio. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 2 comfortable beds-1 regular and 1 Murphy bed, along with a coffee bar and fully equipped kitchen. You're just a 5 minute walk to the beach. Enjoy a dip in the pool, grilling in the gazebo and fish all night long on our large, private fishing pier, no fishing license required. Early check-in avail.

Stay at Sunshine Daydream on Pensacola Beach
Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Newly renovated condo with amazing water views!
Experience the clear blue water and white sand of Pensacola Beach. Enjoy spectacular views of Pensacola Bay from a private 3rd floor balcony. This newly renovated condo offers solid surface floors throughout, a fully stocked kitchen and calming beach decor. The master has a queen size bed, flat screen TV, and ensuite bathroom. The 2nd bedroom offers 2 full size bunk beds. The main living room has another flat screen TV, comfortable couch and is a perfect place for your group to gather.

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p
Welcome to The Diving Dolphin... a 2 bedroom/ 2 bathroom condo located in Emerald Isle Condominium complex~ Directly on Pensacola Beach! This beautiful condo is located on the 5th floor and overlooks the stunning waters of the Gulf of Mexico! Come on in and relax- this condo has it all! The condo has a capacity to comfortably sleep 6. We will send you a welcome packet with details about the complex, unit and area! ~COMPLIMENTARY BEACH CHAIR & UMBRELLA SET UP MARCH - OCTOBER!~

Navarre Beachfront Condo
The VIEWS!! With no high-rises for 1/2 a mile to the west and none for miles to the east, Sundunes literally has the best views in Navarre. Our 5th floor east-corner unit offers unobstructed views of the Sound and the Gulf all from the private balcony. Enjoy all the benefits of a low-density condo with private pool, picnic tables, and barbecue grills. Best of all, relax on the snow-white sand and crystal-clear turquoise waters with NO crowds! Ask about SNOWBIRD discounts!!

The Sandy Secret
Welcome to "The Sandy Secret" one of Navarre's Best Kept Secrets. You will love this newly renovated waterfront beauty. Here you will find the best amenities including: gated pool, private beach, gazebo with grills, gated pier, wifi, cable, elevators, and sooooo much more. The Sandy Secret has everything you are looking for in a vacation spot. Comfort, Style, and Priceless Views. Experience Navarre Beach like never before. See why it was voted The Most Relaxing Beach.

The Purple Sunset-200ft to Beach w Pool
Relax with the whole family at this peaceful beach house on Navarre Beach, FL. 200 feet from the Santa Rosa Sound and 500 feet from the beautiful Gulf of Mexico. A community pool is located literally in your backyard! This Airbnb is 1,320 square feet with 3 beds, 2 baths and a bonus room. Whether it's at the beach, pool, or with friends/family, you will absolutely love it here! We look forward to you creating memories at this heavenly escape. See you soon!

Soundside Paradise
Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

1.5 mi to Beach-New Pool! Smart home-Modern Decor!
Joey’s place is a beautiful home in Navarre, Florida, less than 1.5 miles to the beach with a newly added pool (not heated) in June 2024! You'll have the home to yourselves (office & master closet locked). Close to restaurants and shopping, modern décor, smart home, garage parking. Pool added in June 2024. Extended Patio added in September 2024, 8 ft privacy fence added in December 2024. Mural painting on fence surrounding pool Summer-Fall 2026

Gulf-Front Sunsets on Quiet Navarre Beach
Wake to emerald Gulf views and unforgettable sunsets from the balcony of this cheerful beachfront retreat on quiet Navarre Beach. This comfortable 2-bedroom corner condo offers a relaxed coastal atmosphere, thoughtful touches, and direct access to one of Florida’s most beautiful and uncrowded white sand beaches. Enjoy morning coffee on the balcony, long beach walks, and evenings watching the sun set over the Gulf.
Popular amenities for Santa Rosa Island, Florida rentals with a pool
House rentals with a pool

Sunny Side: Awesome Waterfront Unit with 4 Kayaks

The 30A Beach House | Private Beach + Dune Pool

Poolside Family Retreat w/ Hot Tub & Game Room

Sugar Sand Cottage at Destin Pointe

Aloha Pool House- Stay Local, Live Aloha

Gulf Breeze Oasis-Pool, Hot tub, BBQ, nearby beach

Good times & tan lines! Only 5 miles to the beach!

Kokomo Key on Navarre Beach - Private Pool
Apartment rentals with a pool

Luxury Destin 1BR - Jetty East Beach Resort Condo

Beachfront Bliss: Walk to Dine & Play on Sands

Navarre Beach Gulf front luxury

1203 Oceanfront Pelican Beach: Pools/HTubs Fab Loc

Tide Together on the Gulf at Beach Colony East

Footsteps away from beautiful beaches 🏖🏝⛱

Amazing Ocean Views, Oceanfront Condo, Renovated!

Beachfront Condo • Pool & Resort Perks
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Luxury Gulf-Front Penthouse w/ Panoramic Views

Remodeled~ Private Heated Pool | Game Room | Bikes

Beautiful beachfront condo with Stunning Gulf View

Beach Club 1906 - 𝑷𝒂𝒓𝒂𝒅𝒊𝒔𝒆 𝑭𝒐𝒖𝒏𝒅

Beachfront Balcony Views | Resort Pool | Sleeps 8

Salt & Serenity | Private Pool • Minutes to Beach

Gulfgate Destination 0205 2BD/2BA

Gulf-Front Luxury | Surfside 11th Floor | #1109
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- Destin Beach
- Perdido Key Beach
- Crab Island
- Destin Harbor Boardwalk
- Alabama Point Beach
- Seacrest Beach
- Opal Beach
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Flora-Bama Lounge
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- HarborWalk Village
- Fort Walton Beach Landing
- The Boardwalk on Okaloosa Island
- Henderson Beach State Park
- Topsail Hill Preserve State Park
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Jade East Towers
- The Track - Destin
- Destiny East





