
Holiday rentals with a pool in Santa Rosa Island, Florida
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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.

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.

Comfy 1 Bedroom with Pool at Sunset Harbor Condos
Cozy 1 bedroom, 2 bath unit on the 1st floor offers a view of the Santa Rosa Sound from the balcony. Your vacation starts the moment you walk in the door The sugar white sands of the beach and emerald waters of the Gulf are a short walk or 1 minute drive away. The pool is just outside the building near the outdoor grills. The kitchen is well equipped for cooking. The bedroom features a king size bed and TV. The primary bath has a tub/shower combo. You will love this quiet private community.

Fun, sun, sand, and rest. Enjoy your stay with us.
When you stay at this centrally-located place, your family will be close to everything. The home is ranch-style and located on the canal in a fast-growing beachy community. Minimum stairs if you walk down to the canal. Take advantage of the local golf course which is minutes from the home. Enjoy the beautiful weather, shopping, and the local beaches (Navarre, Pensacola, and Destin) then come home to relax in your home away from home. We do not host parties or special events. Non smoking home.

Waterfront, beach, dock - your Salty Air Retreat!
Embrace island living in our little corner of paradise! This beautiful, family friendly home offers you the ultimate getaway with the clear, calm waters of the Sound right outside your door and the emerald green waters of the Gulf across the street. Swim, fish, and paddle board from your own backyard. Or just enjoy the view from your hammock as your kids build sandcastles on the private white sandy beach. Discover for yourself why Navarre Beach has been named "Florida's Most Relaxing Place"!

Bluewater 306 Direct Gulf Front, HUGE Wrap Balcony
Bring the whole family together in this beautifully designed & thoughfull laid out beachfront condo. Offering spectacular views, multiple generous living areas & comfort for every generation. With room to gather & space to unwind, this home is perfect for grandparents, parents & kids or friend groups to share unforgettable beach days to enjoy together without feeling crowded. With panoramic views from floor-to-ceiling windows, this spacious condo offers breathtaking scenery sunrise to sunset.

Heated saltwater pool | Pet Friendly | Family home
Welcome to Whispering Sands, your ideal retreat for family relaxation. This centrally located Gulf Breeze oasis offers proximity to shopping, dining, the Gulf Islands National Seashore, and Pensacola Beach's pristine shores, all within a 10-minute drive. Step into a rejuvenated space adorned with new furnishings, flooring, and a fresh paint scheme. Bask in the serenity of the enclosed outdoor seating area or take a refreshing dip in the heated saltwater pool. Your tranquil escape awaits!

Best view on the beach! Beach gear included!
Beautiful 1 bedroom, 1.5 bath condo sleeps 6. Bring your swimsuits and get ready to relax! Condo is on 12th floor, tower closest to the pier. - 1 bedroom with king size bed, cozy bunk area for kids, and gel foam mattress on fold-out sofa. (ALL MATRESSES NEW IN SEPTEMBER 2025). - All linens and towels provided, including beach towels! - 2 beach chairs, 2 boogie boards and a beach umbrella included - Washer & dryer - Fully equipped kitchen to enjoy dinner with a view - Wi-Fi & cable

Beachfront Condo • Pool & Resort Perks
Welcome to Pensacola Perch, an 8th‑floor beachfront condo offering expansive views of Pensacola Beach—perfect for dolphin watching and catching the Blue Angels airshow. This modern 2BR/2BA condo sits in the highly sought‑after Emerald Isle gated resort, where guests enjoy premium amenities including direct beach access, two swimming pools, a hot tub, sauna, and a beachfront fitness center. From March–October, enjoy complimentary beach chairs and an umbrella from La Dolce Vita.

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.

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!

Bayside Retreat-Panoramic Sunset Views
Bayside Retreat is a renovated 2nd floor one bedroom. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 3 comfortable beds, King, Day Bed w/Trundle and Queen Sofa Bed, along with a large private balcony and fully equipped kitchen. NOW OFFERING 2 NIGHT DISCOUNTED STAYS MAY THROUGH AUGUST. COMPARE TO LOCAL HOTELS AND SAVE HUNDREDS!!!
Popular amenities for Santa Rosa Island, Florida rentals with a pool
House rentals with a pool

Historic Pool Cottage! Dog Friendly

Poolside Family Retreat w/ Hot Tub & Game Room

Sugar Sand Cottage at Destin Pointe

Pool • Hot Tub • Opt Golf Cart | WHAT-A-BEACH

1.5 mi to Beach-New Pool! Smart home-Modern Decor!

Historic Downtown Bayfront Home Pool Mins to Beach

The Purple Sunset-200ft to Beach w Pool

Dolphin Watch: Lovely Waterfront Unit with Kayaks!
Condo rentals with a pool

Beachfront Bliss: Walk to Dine & Play on Sands

Beach Haven l Beautiful Lagoon Pool & Ocean View

Navarre Beach Gulf front luxury

Prime 30A Location/Pool/200 feet to beach/Wi-Fi

Thoughtfully Hosted Gulf-Front on Navarre Beach

Stay at Sunshine Daydream on Pensacola Beach

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p

Steps to Private Beach • Heated Pool • Gulf Views
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Navarre Bay Views

Private Saltwater Pool Home Near Pensacola Beach

The Bamboo Oasis

Bimini House

Beach Club 1906 - 𝑷𝒂𝒓𝒂𝒅𝒊𝒔𝒆 𝑭𝒐𝒖𝒏𝒅

Private Pool, Steps to the beach, Golf cart

Tide Together on the Gulf at Beach Colony East

Beachfront - "Weekend At Benny's"
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Perdido Key Beach
- Opal Beach
- Henderson Beach State Park
- Village of Baytowne Wharf
- Seacrest Beach
- Navarre Beach Fishing Pier
- Flora-Bama Lounge
- Johnson's Beach, Gulf Islands National Seashore
- Alabama Point Beach
- Blue Mountain Beach
- Grayton Beach State Park
- HarborWalk Village
- Gulf Breeze Zoo
- Topsail Hill Preserve State Park
- Fort Walton Beach Landing
- Jade East Towers
- The Boardwalk on Okaloosa Island
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Destiny East
- Pensacola Bay Center





