Vacation rentals with a pool in Pensacola Beach

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Top-rated rentals with a pool in Pensacola Beach

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Guest favorite

Home in Gulf Beach

4.98 out of 5 average rating, 117 reviews

Come stay at Seas~the~Day!! 6th Floor magic!

Come stay at Seas the Day and relax on your private balcony while taking in breathtaking, 6th floor views of the beautiful Gulf of Mexico. We are located minutes from Pensacola NAS along with lots of other restaurants and shopping venues. We fell in love with this 6th floor, cozy condo with views that connect you to the sugar-white sand beaches and sparkling blue gulf waters. The condo is very quiet and easily accessible to the elevator, pool, ocean, grilling area and parking. HAPPY BEACHING!!

Guest favorite

Condo in Pensacola Beach

4.97 out of 5 average rating, 151 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.

Guest favorite

Condo in Pensacola Beach

4.95 out of 5 average rating, 122 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 favorite

Condo in Orange Beach

4.92 out of 5 average rating, 122 reviews

Summerchase beachfront best fall rates book now!

Summerchase Condominium is in the heart of Orange Beach, Alabama right on the Gulf of Mexico. This 10th floor condo has fabulous unobstructed views of the gulf looking east and west! Our condo is the largest 2 bedroom, 2 bathroom floor plan that Summerchase has to offer. The condo has been updated with a beautiful new kitchen and bathrooms. It has a leather sleeper sofa and loveseat in the living room. The facility is a low density building with two elevators to get you to the beach faster!

Guest favorite

Condo in Pensacola

4.96 out of 5 average rating, 150 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!

Guest favorite

Guest suite in Gulf Breeze

4.95 out of 5 average rating, 118 reviews

Cozy Suite | 2BD/1BA | Private Pool and Backyard

Welcome to Bella Blue! Our beautiful and newly renovated Pool Oasis. Quiet private 2 BR / 1 BA apartment with a private crystal clear pool/ inviting firepit and more. Private fenced spacious backyard for pets. Only 6 Miles from beautiful Navarre beach. Hang out in our family friendly play pool or head to the emerald waters of Navarre beach. Located one mile from the Gulf Breeze Zoo, 15 miles from Pensacola Beach. Conveniently located for shopping /restaurants. We hope you enjoy! - Sonya

Guest favorite

Condo in Pensacola Beach

4.88 out of 5 average rating, 120 reviews

Sugar Sand Beach Retreat at Villas on the Gulf

Welcome to Sugar Sand Beach Retreat! You're just a lovely stroll away from the white Sugar Sand beach & gorgeous emerald water of the Gulf of Mexico, ranked #1 Florida Beach in USA Today's 10 Best Reader's Choice Award, 2018 and #4 Best Beaches in America by TripAdvisor, 2019. Our 2 bedroom condo with private entrance & covered parking,comfortably sleeps 6. Enjoy the beautiful foliage on your private balcony overlooking the pool. Or relax by the lagoon to watch the ducks and turtles.

Guest favorite

Guesthouse in Pensacola

4.98 out of 5 average rating, 255 reviews

Pet Friendly, Pool, Hot Tub, Fenced yard.

This cozy one bedroom one bathroom guest house is waiting for you! The guest house is tucked away in a quiet neighborhood in our backyard and includes a kitchenette with washer and dryer. Stay a little while or a while! We have a big fenced in backyard for your pet to play in, a pool to swim in, a grill to cook on, a hot tub to soak in, a firepit to sit by and a hammock to nap in. It's time to Relax! We are just a 16 mile drive to the beach. We would love for you to come and visit!

Guest favorite

Guesthouse in East Hill

5 out of 5 average rating, 126 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 favorite

Guest suite in Gulf Breeze

4.91 out of 5 average rating, 180 reviews

East Bay Getaway - Studio with Pool & Hot Tub

Welcome to East Bay Getaway, a private studio with modern conveniences you expect. This clean and comfortable room with private entry is an attached MIL suite in a home on more than an acre. It features a kitchenette (no stove), high-speed WiFi, 32" smart TV, and dedicated HVAC system. Plenty of outdoor space to enjoy, with a large pool and hot tub. A bike/walk path is directly across the street, which goes for miles either direction.

Superhost

Rental unit in Pensacola

4.8 out of 5 average rating, 152 reviews

Caribbean Blue steps from the beach

The condo is located only 200ft from the unspoiled sugar-white beach of Perdido Key. You'll feel right at home the moment you step inside its beautiful interior, boasting unique teak furniture, original artwork by owner, nautical touches, and calming colors. This is NOT a beachfront property. The condo overlooks a swimming pool. No sea view. Sleeps 4 plus an infant. No unaccompanied guests under 25.

Guest favorite

Condo in Gulf Shores

4.96 out of 5 average rating, 170 reviews

Long Walks & Sunsets * Quiet End of the Beach

Perfect getaway condo at the quiet end of Gulf Shores! Beautiful view of Little Lagoon. Elegant Beach Condo here at Summer House West in Gulf Shores, Alabama. A 1 Bedroom * 1.5 Bath place for intimate getaway or for your small family or just coming by yourself to have time for yourself!