Holiday 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 favourite

Condo in Pensacola Beach

4.97 out of 5 average rating, 132 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.

2 – 9 Jan

$1,944 AUD total

Guest favourite

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.

24 Apr – 1 May

$1,343 AUD total

Guest favourite

Guest suite in Gulf Breeze

4.9 out of 5 average rating, 144 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.

7 – 14 Sept

$1,325 AUD total

Guest favourite

Cottage in Pensacola

4.98 out of 5 average rating, 421 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.

5 – 12 Dec

$1,742 AUD total

Guest favourite

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!

13 – 20 Nov

$2,028 AUD total

Guest favourite

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!

18 – 25 Oct

$2,819 AUD total

Superhost

Townhouse in Pensacola

4.87 out of 5 average rating, 142 reviews

Herons Nest: Gorgeous Waterfront Unit with Kayaks!

Welcome to Heron's Nest! Our oasis sits on a calm, private, shallow cove of Perdido Bay, providing FANTASTIC balcony views AND the perfect place for families to relax, swim, play, & paddle safely, all directly behind this waterfront unit. This 2 bed/2.5 bath sleeps 6 and includes a fully stocked kitchen, laundry, & 2 Kayaks! Spend all day enjoying the onsite beach, heated community pool, kayaking, swimming, etc, or take a quick 5 minute drive to Perdido Key Beaches, restaurants, & more!

27 Jan – 3 Feb

$1,752 AUD total

Guest favourite

Condo in Orange Beach

4.95 out of 5 average rating, 128 reviews

Beachfront Luxury Condo with Stunning 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.

31 Jan – 7 Feb

$1,839 AUD total

Guest favourite

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.

11 – 18 Sept

$1,366 AUD total

Guest favourite

Apartment in Pensacola

4.87 out of 5 average rating, 501 reviews

Hermosa Flor apartment( Duplex).

A beautiful water front privet apartment, DUPLEX(studio, open concept ) with a nine feet deep pool available and the beach ( only 3 min away). This apartment is across the canal from a sandy beach which is a great relaxing time for a family or singles to have fun and enjoy activities like fishing, boating, and other fun things on the water. the apartment itself is located in a calm and peaceful area. Pool it is complementary!!!!! Sharebel backyard and pool.

15 – 22 Dec

$1,663 AUD total

Guest favourite

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.

30 Dec – 6 Jan

$1,846 AUD total

Guest favourite

Guest suite in Pensacola

4.87 out of 5 average rating, 103 reviews

Hidden gem with private pool! Centrally located!

The Hideaway is a completely private guest suite, close to Pensacola Beach, downtown Pensacola and Pensacola Airport! There is also a private swimming pool exclusively for guests to use! We can accommodate up to 4 guests! There is one bedroom with a queen size bed and a pull out, queen size sofa bed in the living room. There is also a kitchenette with a mini fridge / freezer, a microwave, and a Keurig coffee maker.

17 – 24 Jan

$1,699 AUD total