Vacation rentals with a pool in Pensacola

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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 favorite

Condo in Orange Beach

4.97 out of 5 average rating, 361 reviews

Direct Gulf Front Studio on the Beach.

You'll love the DIRECT GULF FRONT view of the beach from the private balcony of this studio! Enjoy a cup of coffee or late night drinks listening to the sound of the waves. Just steps from the sandy white beaches and the clear emerald waters. Newer furnishings and whole unit freshly painted. New dishwasher and counters, ductless AC, queen sized bed and full size pull out sofa, remodeled bathroom with walk-in shower, large flat screen TV, updated full kitchen, washer/dryer in unit and Free WiFi.

Dec 22 – 29

G$31,306 GYD per night

Guest favorite

Place to stay in Pensacola

4.9 out of 5 average rating, 188 reviews

Our House Yall's House

5 Miles from 2 I-10 ramps, 25 mins to NAS, 30 mins to 2 different beaches - Pens Bch & Perdido Key, 3 miles to equestrian, 4 miles from NFCU. We have a private entrance, walk-out basement. There are other bedrooms if necessary; however, those would be in our living space & more $$. We can accommodate up to 6 guests. During warmer months, pool and tiki are beautiful, another open patio and outside cooking - grill. Area inside has microwave, coffee pot, refrigerator, toaster oven, 52" t.v.

Dec 15 – 22

G$18,276 GYD per night

Guest favorite

Condo in Pensacola Beach

4.97 out of 5 average rating, 131 reviews

The Flamingo Flat @ Villas on the Gulf

🦩Welcome to the Flamingo Flat! PLEASE READ FULL LISTING. This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach. For great shopping, dining and 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.

Dec 29 – Jan 5

G$30,500 GYD per night

Guest favorite

Guest suite in Gulf Breeze

4.9 out of 5 average rating, 143 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 11 – 18

G$20,193 GYD per night

Guest favorite

Cottage in Pensacola

4.98 out of 5 average rating, 420 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 2 – 9

G$30,569 GYD per night

Guest favorite

Condo in Pensacola

4.98 out of 5 average rating, 117 reviews

This is the one! Perfect Getaway near the beach.

Welcome to a place you will want to return to time and again. Fresh renovations, all the amenities! Steps away from a Tiki bar and huge outdoor pool/hot tub! Live music almost nightly! Parking right out front! Johnson and Orange Beach are minutes away. Our goal is to make sure you have the best possible time! You deserve a break. The couch pulls out to a queen bed. Enjoy full kitchen, large shower, fitness center, indoor and outdoor pool and if something feels like it’s missing, let us know!

Jan 16 – 23

G$29,986 GYD per night

Guest favorite

Condo in Orange Beach

4.91 out of 5 average rating, 273 reviews

PHX 3143 On Beach, Pools and Spas

NOTE>>One Elevator out 11.2023 thru 5.2024. BEACH REFURB PROJECT IS COMPLETE! You’ll love this GULF FACING NEST for your beach stay. 1BR/1BA, King Bed, Queen sofa sleeper, Spa bath, slip covered furniture, 55" Samsung TV with FREE cable, & FREE internet. Amenities include: outdoor and indoor pool, hot tubs, sauna, racquetball and tennis court, shuffle board, fitness center, and arcade. Across from Live Bait - Bar& Live entertainment, Ruby Slipper best brunch place. Parking/ stay is $55.

Dec 23 – 30

G$34,181 GYD per night

Guest favorite

Condo in Pensacola

4.99 out of 5 average rating, 116 reviews

MELODY OF THE SEA - ON THE BEACH- INCREDIBLE VIEWS

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! No roads to cross. Stunning panoramic sunset views! Guests love the option of an indoor heated pool and outdoor pool and hot tub overlooking the ocean. A contemporary electric fireplace in the living room & bedroom is perfect for those cozy mild winters for your stay on the beach. Enjoy a king size bed in the master... nautical bunkbeds with port holes and queen sleeper sofa in the main living areas. Reserve Your Time Away Today!

Jan 23 – 30

G$33,675 GYD per night

Guest favorite

Condo in Navarre

4.97 out of 5 average rating, 103 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.

Dec 26 – Jan 2

G$27,349 GYD per night

Guest favorite

Guest suite in Pensacola

4.88 out of 5 average rating, 414 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 game room! It's set up like condos.

Aug 20 – 27

G$23,259 GYD 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 .

Sep 16 – 23

G$20,550 GYD per night

Guest favorite

Condo in Pensacola

4.95 out of 5 average rating, 172 reviews

Updated Coastal Chic Villa @ Purple Parrot Resort

Relax and enjoy your stay in this newly renovated 1BR/1BH, decorated with a bright color scheme and located in an island paradise. The Purple Parrot is a gated vacation resort that embodies the care-free lifestyle of the islands. The resort is just minutes away from the beaches, marinas and restaurants that make this barrier island a must visit! Our unit is just a few steps from the giant outdoor pool, complete with a grotto waterfall and an island hot tub.

Mar 26 – Apr 2

G$30,959 GYD per night