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Holiday rentals with a pool in Downtown Pensacola

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Downtown Pensacola

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

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Top Guest favourite
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.
Home in East Pensacola Heights
4.92 out of 5 average rating, 106 reviews

Relaxing Getaway with Pool/Hot Tub Near Downtown

Picture your family enjoying the pool & hot tub while you grill out in the large private backyard, or lounge in the comfy screened in porch seating area of this peaceful getaway! Located b/t the bayou & scenic bluffs overlooking the bay, our home is close to all the area has to offer! Relax on the beach, visit the fishing pier or historic downtown's upscale dining/shopping. 1 block from Exchange Park which has baseball/softball fields, a playground, free wifi, walking path/trails & picnic areas!

Top Guest favourite
An aerial view showcases the townhome situated along the coastline, with the Gulf's waves gently breaking in the background. The neatly arranged buildings reflect a clean layout, while palm trees and a parking area are visible below, highlighting the nearby beach setting.
Condo in Pensacola Beach
4.99 out of 5 average rating, 114 reviews

Spacious Townhome for Families w/ Beach+Bay Access

Come enjoy the very best of beach life! This Boardwalk townhome is steps from the famous white sand of the Gulf while also offering community pool access & a private, sandy beach on the calmer waters of the bay that is perfect for children to enjoy. This spacious 2 bed/2.5 bath unit (King in master!) has an open layout with beautiful furnishings & outdoor living space on all 3 levels. Plenty of natural light & some Gulf views from each of the balconies you can access from every room in the home.

Top Guest favourite
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 Pensacola Beach
4.93 out of 5 average rating, 108 reviews

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

When you stay at this centrally-located place, your family will be close to everything. The home is ranch-style and located on the canal in a fast-growing beachy community. Minimum stairs if you walk down to the canal. Take advantage of the local golf course which is minutes from the home. Enjoy the beautiful weather, shopping, and the local beaches (Navarre, Pensacola, and Destin) then come home to relax in your home away from home. We do not host parties or special events. Non smoking home.

Top Guest favourite
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.
Home in Downtown Pensacola
4.91 out of 5 average rating, 212 reviews

Historic Downtown Bayfront Home Pool Mins to Beach

The Bayfront Manor brings the best of both worlds to your vacation or business stay in Pensacola. Located 5 min walk from historic downtown, Seville Square, and Palafox Street, the location is ideal for all dining, nightlife, and events. The home is positioned on the corner of Bayfront Dr allowing for great water views of Pensacola Bay. The best beaches on the Gulf are only a 10 min drive. The location is also great for wedding parties as the Barkley House and Christ Church are walkable.

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
4.96 out of 5 average rating, 193 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 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, 202 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.

Guest favourite
A dining area features a large wooden table set with white plates and blue napkins, surrounded by gray chairs. The kitchen, with gray cabinetry and stainless steel appliances, is visible in the background, while beach-themed decor accents the walls.
Townhouse in Pensacola
4.96 out of 5 average rating, 129 reviews

Turn & Slip Inn w/pool to this luxe 3BR townhouse

Your family will be close to everything in this modern and roomy home. Visit downtown attractions just a 5 min drive away or lounge at the pool after coming back from the beach, just 15 min away. Head out to the nearby farmers’ market and craft a meal in the fully stocked kitchen. Enjoy a drink, away from any bugs, in the screened in patio while grilling up some fish from Joe Patti’s seafood market. No matter what you choose you’ll enjoy your relaxing stay at the “Turn and Slip Inn”!

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, 173 reviews

Funky Flamingo~ Guest House~ Pool & Kitchenette

This charming East Hill bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & patio. 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!

Guest favourite
The image captures the nighttime view of a screened-in pool area, illuminated by blue lights. The architectural structure showcases a modern design, with clear visibility of the surrounding landscape featuring trees and grassy grounds. Soft lighting enhances the atmosphere, suggesting a serene outdoor space.
Tiny home in Pensacola
4.97 out of 5 average rating, 157 reviews

Tiny Home Pool View 25 Mins to Beachb

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 located in the backyard 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.

Guest favourite
Home in Pensacola
4.93 out of 5 average rating, 109 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

PLEASE READ entire description to ensure accurate expectations. Relax while the kids play! Enjoy a private pool (seasonally heated), bubbling hot tub, and A/C game room packed with fun. Parents can unwind in the new massage chair or simply enjoy the peaceful backyard oasis. Centrally located—just 10 min to Downtown, 20 to Perdido Key, and 30 to Pensacola Beach—this family retreat blends relaxation, comfort, and connection for your perfect getaway!

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, 200 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.

Top Guest favourite
An aerial view captures a family-friendly home nestled in a spacious yard with lush greenery. A private, crystal-clear pool is seen in the backyard, surrounded by patio space. The property is bordered by a fenced area, providing a sense of seclusion and tranquility.
Home in Pensacola
5 out of 5 average rating, 117 reviews

Blue Angels Haven | Central Pensacola Pool Retreat

This family-friendly 3BR, 2BA home in Pensacola is perfect for up to 6 guests. Enjoy a private backyard oasis with a sparkling pool, ideal for relaxing or family fun. The spacious interior features a fully equipped kitchen and cozy living area. Located just minutes from Pensacola Beach, local attractions, Navy bases, this home offers the perfect balance of comfort and convenience for your next getaway. Please see why I have 100+ 5 star reviews!

Popular amenities for Downtown Pensacola rentals with a pool

When is the best time to visit Downtown Pensacola?

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Avg. price$199 NZD$197 NZD$184 NZD$204 NZD$229 NZD$232 NZD$287 NZD$215 NZD$195 NZD$174 NZD$168 NZD$177 NZD
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Quick stats about holiday rentals with a pool in Downtown Pensacola

  • Total holiday rentals

    Explore 10 holiday rentals in Downtown Pensacola

  • Nightly prices starting at

    Downtown Pensacola holiday rentals start at $177 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,960 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Downtown Pensacola holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Downtown Pensacola rentals

  • 4.9 Average rating

    Downtown Pensacola stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

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

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