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Vacation rentals with a pool in Pensacola

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pensacola

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
A cozy bedroom features a spacious bed covered in a light blue quilt. Two matching pillows are positioned at the head of the bed. A large window offers views of the surrounding landscape, with a picture of a coastal scene displayed above the bed.
Condo in Navarre Beach
4.95 out of 5 average rating, 168 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, private fishing pier, no fishing license required. Early check-in avail.

Top guest favourite
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
5 out of 5 average rating, 175 reviews

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!

Top guest favourite
The living area features a comfortable gray sofa set, a white coffee table, and a ceiling fan. Natural light enters through sliding glass doors leading to a private patio. An open kitchen with wooden cabinetry and a dining area is visible, highlighted by bar stools at the counter.
Condo in Pensacola Beach
4.97 out of 5 average rating, 205 reviews

$0 clean fee! Beachside/pool view/king bed/jacuzzi

Perfect little place for couples or small families to get some R&R. This condo has a poolside view in a lovely little complex, and is just one building back from the beach - steps from paradise! The Gulf boasts some of the most beautiful beaches in the world, and this is the perfect location tucked away from the busy crowds but still close to restaurants, activities, live music, national parks, and a world class spa. The condo is well-equipped and recently updated in October 2022. Come enjoy!

Guest favourite
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 Beach
4.92 out of 5 average rating, 133 reviews

Sunset on the Bayou near NAS/Downtown Pensacola

If you’re looking for a quiet get-away on the water, you will find it here. Our cozy 2 bed/2 bath condo is like a cottage by the sea in a condo setting. Relaxing coastal decor and a beautiful view from the balcony make our home enjoyable inside and out. Enjoy all the amenities of home, sunbathe by the pool, fish from the dock, relax on the balcony, grill out on the lawn. Its all here. Just a short drive from Pensacola NAS, Pensacola Beach and historic Downtown Pensacola. (No pets allowed)

Top guest favourite
A private balcony offers sweeping views of the Gulf of Mexico, showcasing the clear blue waters and soft sandy beach below. The horizon merges sky and sea, creating a serene coastal scene. Beach chairs and umbrellas are positioned along the shoreline, inviting relaxation.
Condo in Pensacola Beach
4.98 out of 5 average rating, 214 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of Mexico from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach! Nothing separates you from the best white-sand beach on the Gulf Coast. This beach condo boasts a vibrant interior filled with beach-themed accents, a private balcony with sweeping ocean views, and access to 2 pools (1 heated) and a hot tub. Enjoy the best restaurants and shopping on the beach, all within a short walk.

Top guest favourite
A serene backyard space features a clear blue pool surrounded by lush greenery. Sunlight filters through the trees, and a variety of plants decorate the perimeter. Lounge chairs are positioned near the pool, providing a comfortable area to relax and enjoy the outdoors.
Home in Pensacola
4.95 out of 5 average rating, 209 reviews

Flamingo On Fisher In The Heart Of Pensacola

Make this home your destination to relax and unwind. The backyard itself will be your special place. The house is perfect for a group to relax and unwind. We are fully equipped with amenities to ensure you feel at home. Centrally located, we are close to everything that makes Pensacola the perfect place to vacation. Pensacola Beach is 9 miles away, 3 miles to the heart of downtown, 3 miles to the airport, 8 miles to NAS Pensacola, 3 to miles Cordova Mall, 2 miles to Pensacola Bay Center.

Top guest favourite
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.
Condo in Pensacola Beach
4.94 out of 5 average rating, 162 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.

Superhost
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.
Condo in Pensacola Beach
4.8 out of 5 average rating, 130 reviews

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

Relax with family or friends at our cozy condo with amazing views of the bay and the Gulf of Mexico. You are mere steps from the gulf's famous sugar white sandy beaches. Enjoy the complex's amenities- sun at the private beach, swim in the pool (unheated), grill on the BBQ and chill at the fire pit. Rent bikes and explore the miles of beach paths and the Fort at Pickens. You're a short drive to the core of the beach where there's shopping, restaurants, bars and family activities.

Guest favourite
This aerial view showcases the resort's dual swimming pools surrounded by lounge chairs. The heated pool is visibly larger and features curved edges. Beyond the pools, the white sandy beach and emerald waters of the Gulf are in view, with beach umbrellas lining the shore.
Condo in Pensacola Beach
4.97 out of 5 average rating, 126 reviews

307 Beach Front Views ~ Special Rate ~ Book Jan 20

Come experience this Beautiful 5 Star Gulf Front Condo, Heated Gulf Side Pool & Hot tub, This Newly Renovated unit offers a Private, Gulf Front Balcony with Amazing Gulf Views, watch Dolphins, Swim in 2 Gulf Side pools, 1 heated, Hot tub on the Gulf. Sleeps 6, Gulf Front Balcony Master on Gulf, 2 BDRM, 2 BA, Master Suite has a luxurious King Size Cloud Lux Tempur-Pedic Bed. Guest Rm 2 has a Euro Top Plush Queen Mattress, LR has a Memory Foam Queen sleeper sofa.

Guest favourite
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 homes in Pensacola
4.98 out of 5 average rating, 187 reviews

Tiny Home Pool View 25 Mins to Beacha

Welcome to our cozy tiny home located in my secured backyard, where a queen-sized bed promises a peaceful night’s sleep and our well-equipped kitchenette simplifies meal preparation. You will have free parking in the backyard located just steps away from the tiny home. Additionally, you’ll have the opportunity to gather around the outdoor fire pit for cozy evenings under the stars. Inside, unwind with a smart TV and stay connected with complimentary Wi-Fi.

Top guest favourite
A comfortable living area is shown with a large sectional sofa and a patterned chair. A round coffee table is centered in the space, complemented by a potted plant. Natural light enters through a window, while a wall-mounted TV displays a scenic beach image.
Townhouse in Pensacola
5 out of 5 average rating, 203 reviews

Stylish Modern Retreat in Downtown + Pool

It's all about the location! This comfortable, spacious townhome is the perfect home base for all your Pensacola adventures. Enjoy the many activities close by: Pensacola Beach (10 miles), Perdido Beach & Johnson's Beach (15 miles), boat charters and fishing, fine dining and pubs, museums, Blue Angel air shows, festivals, Wahoo baseball etc. Or spend the day relaxing at the beautiful pool. Book now to enjoy all the amenities and comforts this home offers.

Guest favourite
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.
Condo in Pensacola Beach
4.93 out of 5 average rating, 106 reviews

Relax Waterfront, Sunset VIEWS, Secluded Beach

Stunning 2-story unit, fully renovated, with plenty of space to accommodate up to 8 people. • Excellent LOCATION on the quite West end of Pensacola Beach. Last complex before National Park at Ft. Pickens • Gorgeous SUNSET views from both balconies • Just a few steps from the GULF OF MEXICO BEACH – perfect for couples and families! • QUIET AND SECLUDED Beach on Santa Rosa Sound

Popular amenities for Pensacola rentals with a pool

When is the best time to visit Pensacola?

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Quick stats about vacation rentals with a pool in Pensacola

  • Total vacation rentals

    Explore 130 vacation rentals in Pensacola

  • Nightly prices starting at

    Pensacola vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 8,750 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    120 of Pensacola vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pensacola rentals

  • 4.8 Average rating

    Pensacola stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Pensacola’s top spots, include Pensacola Museum of Art, Palafox Market, and Bruce Beach

Destinations to explore