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Holiday rentals with a pool in Pensacola Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pensacola Beach

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

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Top guest favourite
A bright living area offers views of the Gulf through expansive glass doors. The space features comfortable seating, including wicker chairs and a cozy sofa. A telescope stands nearby for observing the shoreline, while a balcony with seating is visible beyond.
Apartment in Pensacola Beach
4.99 out of 5 average rating, 139 reviews

Quiet Lux Family Beach Retreat

TWO Gulf-View Balconies • Heated Pool • Gulf & Sound Access • King Suite • Family-Friendly Enjoy a waterfront Pensacola Beach condo with stunning Gulf views and direct beach access. This spacious 3-level vacation rental sleeps 8 and features two private Gulf-view balconies, a chef’s kitchen, and a bright solarium. Walk to both Gulf and Sound beaches or relax by the heated community pool. Quiet Fort Pickens location with easy access to dining, attractions, and the free island trolley—perfect for

Top guest favourite
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.
Apartment in Perdido Key
4.96 out of 5 average rating, 316 reviews

Phoenix X 1105- 1BR Florabama Beach Luxury Suite

This meticulously maintained and beautifully furnished Phoenix 10 condo is the epitome of elegance and sophisticated luxury for the discerning couple or small family seeking respite in a beach resort setting. Sip your morning coffee on your private balcony overlooking the beach and Gulf of Mexico. Situated directly on the beach! Parking available in Association lobby for a $60 fee per stay. Linens, towels and complementary starter package (TP/ paper towels, dish detergent and shampoo provided)

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.
Apartment 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 bright living area features a spacious white sectional sofa adjacent to a light wood coffee table. Floor-to-ceiling glass doors offer expansive views of the ocean and sky, enhancing the openness of the space. A dining set is visible on the balcony.
Apartment in Perdido Key
4.99 out of 5 average rating, 165 reviews

MELODY OF THE SEA - ON THE BEACH- INCREDIBLE VIEWS

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! Beautifully remodeled and updated! This retreat has the rare double windows to enjoy stunning panoramic sunset views! On the beach (No roads to cross)! Resort has indoor heated pool & outdoor pool & hot tub overlooking the ocean. 2 fireplaces in the living room bedroom for those cozy mild winters. King size bed in the master... nautical bunkbeds with port holes & queen sleeper sofa in the main living areas. Reserve Your Time Away Today

Top guest favourite
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 Navarre Beach
4.97 out of 5 average rating, 122 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"!

Top guest favourite
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.
Apartment in Pensacola Beach
4.99 out of 5 average rating, 128 reviews

Beachfront Condo With Pool & Resort Amenities

Welcome to Pensacola Perch, an 8th floor beachfront condo where you will enjoy expansive views of Pensacola Beach–– a perfect vantage point for dolphin sightings & the Blue Angels Air Show. This 2BR/2BA condo is in the sought after Emerald Isle gated resort where guests can enjoy resort amenities such as direct beach access, 2 swimming pools, a hot tub, sauna, & beachfront fitness center. There’s also complimentary use of 2 chairs & an umbrella from La Dolce Vita all through March to October.

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.
Apartment 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!

Top guest favourite
A vibrant welcome sign featuring a flamingo and pineapples is displayed on the door. Inside, a spacious living area includes a white sofa, two black wire chairs adorned with colorful cushions, and a window dressed with sheer curtains, allowing natural light to fill the space.
Apartment in Pensacola Beach
4.96 out of 5 average rating, 175 reviews

The Flamingo Flat @ Villas on the Gulf

🦩Flamingo Flat: Ask about JAN/FEB longer stay discounts! This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach. For great shopping, dining & entertainment you can drive ( less than 3 miles West) to the main hub of P’Cola Beach. Trolley service available during summer months. The beautiful Portofino Island Resort is just 1 mile to the East. MUST BE 25 TO RENT. NO CHILDREN UNDER 12. NO PETS. EARLY CHECK IN MAY BE AVAILABLE FOR AN ADDITIONAL $50.

Guest favourite
A seaside balcony offers a table surrounded by tall, teal chairs. The horizon meets the sparkling blue waters under a clear sky, reflecting sunlight on the surface. The scene invites moments of relaxation and enjoyment of the coastal views.
Apartment in Orange Beach
4.9 out of 5 average rating, 388 reviews

Beachfront - PENTHOUSE - Breathtaking Views!

In the heart of Orange Beach is this luxury condo with gorgeous views of the sugar white beaches & emerald waters. From the balcony you can watch the majestic sunrise or marvel at the dolphins playing. When a break from the beach is needed you can enjoy the many amenities onsite. Orange Beach offers activities for the whole family including restaurants & shopping. After a fun day prepare to make dinner in the well appointed kitchen, relax with the cheerful decor & comfortable sitting.

Top guest favourite
A screened balcony features two light-colored seating chairs and a coffee table, offering a view of the waterway. Tall buildings are visible in the background, and a plush blue area rug enhances the inviting space.
Townhouse in Perdido Key
4.96 out of 5 average rating, 135 reviews

Winter Discounts! Lost Key 3BR Beach & Golf Stay

SNOWBIRDS — WE WANT YOU THIS WINTER! ❄️➡️☀️ Escape the cold! Enjoy discounted, flat monthly rates at “Family Tides,” in Lost Key Beach & Golf Resort This 3 BR/2.5 BA townhome offers: ✔️Gulf views ✔️Resort pools ✔️Private beach club access ✔️5-min walk or complimentary shuttle to the sand Fully stocked kitchen, fast Wi-Fi, washer/dryer, garage parking, & beach gear - all you need for a comfortable long-term stay Perfect for snowbirds seeking sunshine near Pensacola & Perdido Key

Guest favourite
A balcony overlooks the Gulf of Mexico, featuring two red chairs positioned for seaside relaxation. The horizon reflects sunlight, and sandy beach chairs are visible below along the shoreline, creating a serene oceanfront view.
Apartment in Pensacola Beach
4.93 out of 5 average rating, 150 reviews

Sea-Esta Beach Front 2 Free Chairs, Umbrella, Pool

Stunning oceanfront condo located directly on Pensacola Beach. Free Beach Chairs and Umbrella. Free WiFi Master bedroom w king bed and Guest bedroom w two double beds. Full bath in the master and beautiful full walk in shower in guest room. Updated fully equipped kitchen w granite countertops and new stainless steel appliances. Start your day watching the sun rises from your balcony over the Gulf of Mexico and end it watching the sun set over another day in Paradise!

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.
Apartment in Pensacola Beach
4.97 out of 5 average rating, 126 reviews

307 Beach Front Views ~ Special Rate ~ Book Jan 19

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.

Popular amenities for Pensacola Beach rentals with a pool

When is the best time to visit Pensacola Beach?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$232 SGD$228 SGD$299 SGD$276 SGD$344 SGD$436 SGD$483 SGD$331 SGD$276 SGD$273 SGD$247 SGD$231 SGD
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Quick stats about holiday rentals with a pool in Pensacola Beach

  • Total holiday rentals

    Explore 2,090 holiday rentals in Pensacola Beach

  • Nightly prices starting at

    Pensacola Beach holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 47,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,860 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 200 rentals that welcome pets

  • Rentals with dedicated workspaces

    1,050 properties have a dedicated workspace

  • Wifi availability

    2,080 of Pensacola Beach holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pensacola Beach rentals

  • 4.8 Average rating

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

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