Vacation 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.

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Top guest favorite

The outdoor pool is framed by a screened enclosure, providing clear views of the tranquil bay waters. Comfortable lounge chairs are positioned beside the pool, and potted plants add a touch of greenery. A wooden dock extends into the bay, enhancing the serene ambiance.

Home in Navarre

4.97 out of 5 average rating, 192 reviews

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.

LocationFamilyHot tub

Top guest favorite

Condo in Destin

4.99 out of 5 average rating, 231 reviews

100 ft to sand, Corner unit, Hot Tub, Garden view

Step out and hit the beach—just 100 ft to the sugar sand beach from this charming condo. MONTHLY SNOWBIRD PRICING. Featuring a King master suite w/private bath, 2nd King room, plus a bunk-bed cubby for kids with a hall shared bath. Ground level, corner unit. The fully stocked kitchen includes Keurig w/pods. 3 TVs. Private patio. Just steps from pool & hot tub. Wi-Fi, washer/dryer w/starter pods. Stroll to dining and local attractions. 2 FREE parking spots. Rent 25+ unless active duty military.

FamilyLocationLong stay

Top guest favorite

An aerial view captures a beachside community with a blend of buildings and green spaces. The soft, white sand stretches along the shoreline, dotted with colorful umbrellas and beach chairs, providing a visual representation of the beach access available for guests.

Villa in Destin

4.96 out of 5 average rating, 101 reviews

Sandpiper Cove 8140! 500 ft to the Beach!

Free beach setup which includes 1 reserved umbrella and 2 chairs between March 1st and October 31st! 1,100 feet of private beach access owned by Sandpiper Cove! 4 beach towels are provided with unit 8140! 1 of the 5 pools is in the back terrace; steps away from the back porch of the villa! 1 restaurant, 1 beach side bar, a pitch and putt golf course, tennis and pickleball courts all on site. Minutes from several local attractions! About 17 miles from the Destin-Fort Walton Beach Airport!

FamilyValueGrill

Top guest favorite

Apartment in Pensacola Beach

4.93 out of 5 average rating, 110 reviews

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.

FamilyValueBeach

Guest favorite

A cozy bedroom features a spacious king bed with neutral bedding and decorative pillows. Floor-to-ceiling glass sliding doors provide access to a private patio with bay views. A wall-mounted TV and contemporary furniture, including a dresser, enhance the inviting ambiance.

Apartment in Pensacola Beach

4.86 out of 5 average rating, 102 reviews

Twin Tides at Sunset

Navarre Beach is a picturesque coastal destination known for its pristine white sand beaches, clear turquoise waters, and tranquil atmosphere. Located on Santa Rosa Island, Navarre Beach offers a serene and laid-back setting that appeals to visitors seeking a relaxing beach vacation. Navarre Beach is cherished for its unspoiled and less crowded atmosphere compared to some of the more touristy destinations in Florida. It offers a peaceful retreat where visitors can enjoy a slower pace of life.

LocationValueCheck-in

Top guest favorite

A spacious deck overlooks the calm waters of the Sound, framed by a clear blue sky. Two round, textured outdoor poufs are positioned near the railing, inviting relaxation while enjoying scenic views of the shoreline and distant piers.

Townhouse in Pensacola Beach

4.97 out of 5 average rating, 132 reviews

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"!

FamilyLocationQuiet

Top guest favorite

Home in Pensacola Beach

4.97 out of 5 average rating, 132 reviews

Kokomo Key - 2 minutes to Beach - Private Pool

If you've been searching for Kokomo Key... Here it is—your tropical escape to the islands. White sand, turquoise waters… it’s got all the vibes of a place where time slows down and the only agenda is relaxation. Relax with the whole family at this peaceful beach house with a private pool, hammocks, unobstructed views of Santa Rosa Sound, and a 2-minute walk to the stunning Gulf beaches! We are pet-friendly, but please remember to let us know you are bringing your pets by checking the box!

FamilyValueWalkability

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, 148 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.

ValueLocationAccuracy

Top guest favorite

The newly built cottage features a two-story design with light-colored siding, surrounded by lush greenery. A golf cart is parked nearby on a gravel path, adding convenience for exploring the area. Sunlight filters through the trees, creating a serene atmosphere.

Home in Santa Rosa Beach

4.96 out of 5 average rating, 160 reviews

Luxury 30A Cottage w/ Private Pool and Golf Cart

A NEWLY BUILT LUXURY COTTAGE DESIGN BEACH HOUSE WITH PRIVATE/HEATED POOL* AND GOLF CART in the heart of Santa Rosa Beach off 30A. This beach house is nestled among the trees yet only minutes away from the white sandy beaches. Bask in the sun by day and wind down and relax in the outdoor areas surrounded by a peaceful wooded area by night. It is like stepping out of one world directly into another. Come and Relax and enjoy the peace and tranquility of this cozy retreat.

ValueFamilyGrill

Top guest favorite

A modern kitchen is seen alongside a dining area with a table and stools. The open living space features a sofa and accent chair, with natural light filtering in from a large window. A cozy sleeping area is positioned in the background, adorned with soft decor.

Condo in Pensacola Beach

4.88 out of 5 average rating, 354 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.

LocationFamilyBackyard

Top guest favorite

A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.

Home in Pensacola Beach

4.98 out of 5 average rating, 163 reviews

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!

ValueFamilyOutdoor spaces

Top guest favorite

A custom upright piano converted into a bar is displayed, featuring blue lighting and an array of glassware. A colorful art piece hangs above the piano, alongside a unique lamp atop a wine barrel. The modern decor enhances the inviting atmosphere.

Home in Navarre

5.0 out of 5 average rating, 130 reviews

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 Fall 2026

LocationFamilyOutdoor spaces