Vacation rentals with a pool in Pensacola

4.99 out of 5 average rating, 142 reviews

Private Pool-Near NAS-Grills-Game Room FamilySetUp

You have found a home that is loved by so many who come to Pensacola! This home offers so much for families: arcade room, board games, foosball coffee table, cards, the pool, it's full of fun! Guests rave about how clean it is, that pics are accurate & how quiet the neighborhood is yet a simple drive to restaurants, attractions and the beaches. Great for visiting military at NAS/Corry station or events as kite fest, wahoo games, bands on the beach, theater, Friday art nights and parades! BookNow

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Superhost

A spacious saltwater pool is framed by a grassy yard, with clear blue water reflecting the sunlight. Surrounding the pool area are simple landscaping features, and nearby structures provide a glimpse of the home’s inviting layout. Trees provide partial shade in the background.

Home in Bellview

Fam Fun-Spacious Home-BOHO Vibes-Game Room & Pool

Treat yourself to this newly renovated contemporary 3bd/2ba house with saltwater pool. Comes with four 4K smart TVs, Smart Home Security, darts, golf potting, Keurig and K-cups. The living room TV is 75 inches! Unit is perfect for families or small group looking for a homey and fully equipped space - whether you're here for business, needs a transient home, or just enjoying the vacation spots Pensacola and the Florida panhandle are known for. Pensacola Beach & Perdido Key are 17mi and 25mins

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4.92 out of 5 average rating, 112 reviews

5.0 out of 5 average rating, 206 reviews

A private pool area is surrounded by a wooden fence, featuring clear blue water and colorful floats. A shaded seating area with vibrant umbrellas and lounge chairs is visible nearby, offering options for relaxation. The atmosphere is bright and inviting, with a glimpse of the bungalow in the background.

Guesthouse in East Hill

Funky Flamingo~ Guest House~ Pool & Kitchenette

This charming East Hill pool bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & entire back yard. Luxury comforts and amenities, with the highest speed Wi-Fi/streaming services. Casper mattress and pillows with (700 thread count Egyptian Cotton sheets), for an amazing nights rest. Beach chairs, cooler, umbrella and towels provided. Enjoy the new walk-in shower w/ tankless hot water heater. LBGTQIA2S+ friendly!

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4.96 out of 5 average rating, 101 reviews

Our Shangrila: Waterfront Home with Kayaks & More

Welcome to Our Shangrila! This home sits directly on a calm, shallow cove of Perdido Bay, providing the perfect place for families to relax, play, swim, & paddle safely. Come enjoy gorgeous views, coffee on the balconies, & serene waters. This 2 bed/2.5 bath sleeps up to 7 & includes a full kitchen, laundry, 2 kayaks, 2 SUPs, & more! Spend all day right here, isolated from the hustle & bustle. Or take a very short drive to the beaches, dining & more along Perdido Key. Continue for more Details

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Superhost

A bright dining area is furnished with a glass-top table and stylish black metal chairs, accented by greenery in a vase. The space features large windows that provide ample natural light, with wooden beams enhancing the ceiling's height. A modern kitchen area is visible in the background.

4.88 out of 5 average rating, 257 reviews

Vintage Charmer with Tiny Pool Close to Downtown

Great historical Pensacola home with vintage charm & modern comfort. Our favorite part is the Beautiful Kitchen and private Backyard! Enjoy the gas BBQ grill out on the deck or chill in the hammock underneath the palm trees. A welcoming space to spend time with family & loved ones. Enjoy a fun unique atmosphere with a mix of new & vintage furniture & art. Convenient location close to Downtown Palafox Pier, Pensacola Bay Center, NAS Navy Base, local area hospitals, 15 mins from Pensacola Beach.

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A well-furnished living area is depicted, featuring two patterned armchairs and a sectional sofa. A coffee table is centered on a vibrant area rug, while a large flat-screen television is mounted on the wall. Natural light fills the space through a glass door leading to the outside.

4.94 out of 5 average rating, 125 reviews

Downtown Oasis - Pool & Parking

Centrally located in Pensacola's thriving downtown, our poolside oasis is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Full Kitchen, Washer & Dryer, Gas Grill, Garage, and Private Parking. Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. Enjoy your stay in America's first settlement and be sure to check out the VisitPensacola website for events while you're here!

ValueFamilySleep quality

5.0 out of 5 average rating, 154 reviews

Quiet Family Pool Home! Airbnb's Favorite! TOP 1%

Welcome to your quiet Pensacola getaway! The perfect home base for beach days, Blue Angels excitement, and relaxing evenings. Located in a peaceful neighborhood just minutes from Pensacola Beach, NAS Pensacola, and downtown, this clean and comfortable home is ideal for families, couples, military visitors, quick visits or longer stays. Whether you’re here for the sugar-white beaches, aviation events, or a laid-back escape, this home offers space, convenience, and comfort without the crowds.

ValueFamilyAmenities

A private balcony overlooking calm blue waters and a sandy beach. A circular white table with two accompanying chairs is positioned at the edge, creating a space to enjoy the panoramic views of Pensacola Bay.

4.95 out of 5 average rating, 291 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 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.

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4.88 out of 5 average rating, 111 reviews

A spacious living room is furnished with a large sectional sofa and a matching ottoman, set atop a decorative area rug. Natural light is provided by windows, with ceiling fans enhancing the comfortable atmosphere.

Home in Sanders Beach

Private Pool / Two living rooms /Downtown

This 3000sqft home features a private pool, two living rooms, four bedrooms, two bathrooms, a kitchen, and a beautiful sunroom overlooking a private pool! Two families traveling together?? This is the ideal home for you! This home sleeps 10 comfortably but can accommodate more with the use of an air mattress or crib if traveling with a toddler. Located just a few blocks from Joe Patti's, the Blue Wahoo Stadium, and Palafox Street! YOU AGREE TO ALL HOUSE RULES WHEN YOU BOOK. READ THEM.

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A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.

4.99 out of 5 average rating, 157 reviews

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.

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4.89 out of 5 average rating, 103 reviews

A well-lit bedroom features a spacious bed dressed in neutral linens, complemented by warm-toned throw pillows. Two bedside tables with lamps flank the bed, and a piece of artwork depicting a coastal scene hangs above. Natural light filters through the window adorned with sheer curtains.

Home in Gulf Breeze

Modern Dream Home | Heated Pool and a Fire Pit!

Enjoy a fun-filled family getaway at this stylish home, complete with a brand-new outdoor pool and a cozy fire pit in the backyard. Freshly designed interiors feature a King Bed Master, high-end finishes, and stunning artwork. Located just minutes from the pristine beaches of Emerald Coast and downtown Pensacola. This spacious 4-bedroom, 2-bathroom home boasts TVs in 3 out of 4 rooms, an open-concept living area, and plenty of seating. Welcome to our Hidden Gem!

ValueFamilyKitchen

4.98 out of 5 average rating, 169 reviews

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

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!

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Popular amenities for Pensacola rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene backyard is illuminated at night, featuring a sparkling pool surrounded by a deck and lush greenery. A hot tub, positioned under a wooden pergola, adds to the relaxation area, with soft lighting creating a calm atmosphere. Lounge seating and a dining table are visible nearby.

4.93 out of 5 average rating, 120 reviews

Hot tub/ Pool Relaxing Getaway

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Home in Downtown Pensacola

A two-story home features a light blue exterior and a symmetrical design, framed by white columns on the porch. The landscaped front yard is neatly manicured, with low shrubbery and a brick pathway leading to the front door.

Historic Downtown Bayfront Home Pool Mins to Beach

ValueFamilyComfort

4.9 out of 5 average rating, 227 reviews

4.94 out of 5 average rating, 149 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

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4.97 out of 5 average rating, 196 reviews

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

East Bay Hideaway — A Private Waterfront Escape

LocationFamilyGrill

4.93 out of 5 average rating, 123 reviews

A screened-in pool area features a clear, blue pool surrounded by a spacious deck. Lounge chairs are positioned around the pool for relaxation. Lush palm trees and greenery are visible in the background, offering a glimpse of the outdoor environment.

Home in Gulf Breeze

Fun, sun, sand, and rest. Enjoy your stay with us.

LocationFamilyHospitality

4.94 out of 5 average rating, 104 reviews

A panoramic view of the waterfront showcases soft white sands bordered by the calm waters of the Santa Rosa Sound. A palm tree is visibly planted in the foreground, while distant structures hint at the local community. Clear blue skies create a serene backdrop.

Home in Pensacola Beach

Beachfront - “Weekend At Benny’s”

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4.93 out of 5 average rating, 241 reviews

A private backyard features a heated pool surrounded by landscaped areas with palm trees and flowers. A covered porch provides shaded seating options, while lounge chairs invite relaxation by the water. A securely fenced area enhances safety and privacy.

Home in Navarre

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

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An open-plan kitchen and dining area is featured, designed with white cabinetry and modern stainless-steel appliances. A large dining table with wooden chairs provides seating, while a cozy sitting area with a sofa is to one side. Natural light brightens the space through multiple windows.

4.95 out of 5 average rating, 107 reviews

• “Bayou Grande View – Peaceful Pensacola Getaway”

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Condo rentals with a pool

A corner of the living area is presented with large windows offering expansive views of the water. A wooden desk and a light-colored chair provide a workspace, while a soft armchair and small table create a cozy seating arrangement. Natural light floods the space.

4.95 out of 5 average rating, 139 reviews

Relax Waterfront, Sunset VIEWS, Secluded Beach

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4.96 out of 5 average rating, 364 reviews

A modern dining area features a round table with light-colored tableware, surrounded by four white upholstered chairs. Behind the table, a stylish shelving unit displays decorative items against a marbled wall. Expansive glass doors provide a view of the ocean and allow natural light to flood the space.

Condo in Perdido Key

PX 1105 Next to Florabama, Beachfront Luxury Suite

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A serene view of the bay is captured from the balcony, showcasing the calm water and sandy beach lined with outdoor furniture. In the distance, a pier extends into the water, while boats can be seen sailing peacefully, framed by the clear blue sky.

4.97 out of 5 average rating, 141 reviews

Pensacola Beach Condo w/ Great Views (F12)

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A balcony with a circular table surrounded by four plastic chairs features a view of the bay. The scene includes grassy areas and nearby buildings, with palm trees visible in the background under a partly cloudy sky.

4.82 out of 5 average rating, 160 reviews

Bliss on the Bay 2BR 2BA Beach Condo with Pool D7

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A light-filled living space features a comfortable couch adorned with soft cushions. A coffee table rests on a textured area rug, complemented by a small plant. The adjacent dining area and kitchen can be seen in the background, adding to the open and inviting layout.

4.95 out of 5 average rating, 185 reviews

Pelican's Perch @ Villas on the Gulf

ValueFamilyBreakfast

A spacious living area is shown, featuring two gray sofas and a sleek television mounted on the wall. Sunlight filters through sliding glass doors, revealing a view of the balcony. A light blue accent chair and a decorative side table complement the setting.

4.98 out of 5 average rating, 121 reviews

Waterfront, sleeps 7, walk to everything!

ValueFamilyPool

A balcony view overlooks a tranquil sound with soft waves and clouds dotting the sky. Below, a private pool is nestled within a landscaped area, complete with lounge chairs. The beach extends gently along the shoreline, enhancing the relaxed coastal atmosphere.

4.96 out of 5 average rating, 246 reviews

Gulf Getaway+ Waterfront Views *Fully Updated*

FamilyValueParking

4.93 out of 5 average rating, 147 reviews

A serene waterfront view at sunset features a serene bay with multiple sailboats and yachts docked. The sky is painted in soft shades of pink and purple, reflecting on the calm water. A grassy area with kayaks and canoes is visible in the foreground.

Condo in Pensacola

Sunset on the Bayou near NAS/Downtown Pensacola

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Other vacation rentals with a pool

4.98 out of 5 average rating, 224 reviews

A spacious outdoor area is enclosed with a framed structure, featuring soft blue and white lighting along the floor. Potted plants add a touch of greenery, while lounge chairs are neatly arranged within the space, providing a relaxing ambiance for outdoor gatherings.

Tiny home in Pensacola

Tiny Home Pool View 25 Mins to Beacha

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4.96 out of 5 average rating, 26 reviews

Townhouse in Pensacola

Casa Brisa • 3BR • Downtown • Pool • NAS/Beach

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Superhost

The exterior of the Mediterranean estate showcases a two-story structure with a red-tiled roof and large windows. Palm trees surround the property, leading to a private dock extending into the sparkling waters of the Santa Rosa Sound, creating a sense of tranquility and relaxation.

Home in Pensacola Beach

Rare Waterfront Find! Stay 4/25-4/28 or 6/14-6/21

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4.91 out of 5 average rating, 11 reviews

Luxe

A spacious waterfront home is seen from a wooden dock that leads to a sandy beach area. The exterior showcases large windows and a covered patio, surrounded by palm trees. The tranquil water reflects the clear sky, creating a calm atmosphere.

Villa in Pensacola

Luxury Waterfront Home+Private Beach+Infinity Pool

ValueFamilyCheck-in

5.0 out of 5 average rating, 64 reviews

A sparkling blue pool is surrounded by a wooden fence and a vibrant red umbrella. Colorful inflatables float on the water's surface. A cozy seating area is visible indoors, featuring a soft gray couch and a patterned rug, creating an inviting space for relaxation.

5.0 out of 5 average rating, 82 reviews

Pool Pet Friendly Oasis! - The Palm House

LocationValueWalkability

5.0 out of 5 average rating, 13 reviews

Peaceful Coastal Retreat Near Downtown & Beach

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Townhouse in Pensacola Beach

Sunset Social @ The Boardwalk Condo

LocationFamilyGetting around

5.0 out of 5 average rating, 30 reviews