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.

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Guest favorite

Condo in Mary Esther

4.87 out of 5 average rating, 134 reviews

Waterfront Condo with FREE Kayaks

* Right on the waterfront ! *Free Kayaks ($300-$400 value as the same kayaks rent for $ 100/day /kayak) down the road at the rental place. The place is right in front of the water with amazing views of the Santa Rosa sound and Okaloosa island, the pool is 5 steps away. *Large and airy one bedroom, one living room, kitchen and bath, TV in both rooms. Endless summer days at its best. *Kayaks are free to use. *We are 4 miles to the Gulf beach on Okaloosa Island and 9 miles to Destin Harbor.

Dec 12 – 19

€ 117 per night

Guest favorite

Guest suite in Gulf Breeze

4.9 out of 5 average rating, 145 reviews

East Bay Getaway

Welcome to East Bay Getaway, a private studio with modern conveniences you expect. This clean and comfortable room with private entry is attached to a home on more than an acre. It features a kitchenette, high-speed WiFi and a 32" Smart TV . Dedicated HVAC system. Plenty of outdoor space to enjoy and a bike/walk path is directly across the street. Ample parking for larger vehicles/boats. About a 20 min drive to Navarre Beach and Pensacola beach, with places to eat and shop only a few minutes.

Jan 19 – 26

€ 105 per night

Guest favorite

Condo in Navarre

4.9 out of 5 average rating, 145 reviews

Steps to the Beach / Sleeps 4 w/ King BR & 2 BA

Renter must be 25 years or older & residing in the unit for the entire length of the reservation. Add'l guest of all ages welcome No local rentals (<75 miles). MON & FRI check in/out 1st Floor/ King & twin bunks / Sleeps 4 Main bedroom w/ensuite bath/Full bath in hall Crib available w/request 2 Wall mounted TVs Fully equipped kitchen & washer/dryer Towels & sheeted beds. 4 beach towels & cooler Steps from the Santa Rosa Sound & Gulf/affordable vacation w/ pool (not heated), gas grills

Aug 9 – 16

€ 209 per night

Guest favorite

Cottage in Pensacola

4.98 out of 5 average rating, 424 reviews

Eclectic Eco- Friendly Luxe City Cottage

New eco chic cottage features high end touches and appliances in a cozy luxe setting. Sitting on the edge of the downtown jurisdiction, you're never too far away from the action on Palafox Street and a quick jaunt over to the beach. A chlorinated, salt water “stock tank pool” awaits you in the back for a quick dip to cool off or relax. Excellent access to Wahoos Stadium, Sanders Beach, The Oar House, Pensacola Yacht Club, Pensacola Country Club, Joe Patti's, and Pensacola's Naval Air Station.

Jan 3 – 10

€ 152 per night

Guest favorite

Condo in Navarre

4.97 out of 5 average rating, 104 reviews

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, lighted, private fishing pier, where no fishing license is required.

Apr 2 – 9

€ 175 per night

Superhost

Condo in Destin

4.84 out of 5 average rating, 219 reviews

Majestic Ocean Views, Oceanfront Condo, Renovated!

Located right on the beach, this spacious condo has breathtaking unobstructed Gulf views, updated floors and appliances and sleeps six. Decorated in soothing designer colors with a coastal feel, the unit has a bedroom with a comfortable king size bed, flat screen TV and private bathroom; two bunk beds in a hallway alcove, a 2nd bathroom with shower, and open concept full size kitchen with all new full size stainless steel appliances, dining area and living room with a sleeper sofa..

Dec 10 – 17

€ 145 per night

Guest favorite

Condo in Gulf Breeze

4.95 out of 5 average rating, 138 reviews

Fun Mid-Century Modern Beachside Condo on the Gulf

Experience the most beautiful beaches just steps away from your newly remodeled mid-century modern beach condo. The kids (big ones too) will enjoy the 300 Retro Game Arcade System and the 70" Flat Screen TV. Our fun condo sleeps 6 comfortably with a King in the master bedroom and two queens in the second bedroom. All beds have brand new 5 star Zinus 12" mattresses, so you'll sleep like a baby:) You'll find the kitchen is fully stocked and ready to support all your cooking needs.

Dec 12 – 19

€ 157 per night

Guest favorite

Condo in Pensacola Beach

4.93 out of 5 average rating, 118 reviews

Pelican's Perch @ Villas on the Gulf

This renovated 2 bed/1.5 bathroom condo is stocked and ready to go--Just bring your groceries and swimsuits! This quaint little beach condo is the perfect, affordable getaway you are looking for. In less than a two-minute walk from the front door, you can have your toes in the sand, soaking up the sun on the Gulf. It features a carport for private parking, two bedrooms, w/ a King bed in one room, two full beds in the other, a couch in the living area, and a queen air mattress.

Jan 25 – Feb 1

€ 181 per night

Guest favorite

Condo in Pensacola Beach

4.95 out of 5 average rating, 208 reviews

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 a fully stocked kitchen, luxury linens, 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.

Nov 17 – 24

€ 182 per night

Guest favorite

Condo in Navarre

4.86 out of 5 average rating, 279 reviews

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.

Nov 27 – Dec 4

€ 183 per night

Guest favorite

Guest suite in Pensacola

4.88 out of 5 average rating, 415 reviews

Pelican Nest Oasis-Heated Pool/Jacuzzi Tub

Welcome to the beautiful Pelican Nest! Fully-furnished, gorgeous one bedroom apartment in a prime, safe, quiet location in a cul-de-sac; on-site laundry facilities; Private balcony views of the beautiful pool; fabulous park 2 doors away; fully-equipped kitchen, inner-spring, memory foam futon, walk-in closet, dedicated office space; high-speed internet/streaming services! There’s plenty of storage; a fabulous whirlpool tub; bikes and a games! It's set up like condos.

Aug 25 – Sep 1

€ 127 per night

Guest favorite

Guest suite in Gulf Breeze

4.88 out of 5 average rating, 681 reviews

Sunny Studio 3 miles to beach

Calming, sunny, fully-furnished attached studio with private entrance, recently updated kitchenette, & pool. Covid cleaning compliant. Good WIFI. Perfectly located 3.2 miles to Casino Beach, & Shoreline Park trails that take you straight to the Pier. Great for biking, walking or jogging! Fully stocked with beach chairs, indoor/outdoor towels, boogie boards, coolers etc. The backyard is beautiful & there's a private pool must be 18 to use.Assigned driveway parking .

Oct 18 – 25

€ 108 per night