Holiday rentals with a pool in Downtown Pensacola

Funky Flamingo~ Guest House~ Pool & Kitchenette

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

Private Pool-Near NAS- Grills-Arcades-FamilySetUp

You have found a home that is loved by so many who come to Pensacola! This home offers so much for families: arcade games, board games, foosball coffee table, cards, the pool, it's full of fun! Guests rave about how clean it is, that pics are accurate & how quiet the neighborhood is yet a simple drive to restaurants, attractions and the beaches. Great for visiting military at NAS/Corry station or fall events as The Fair/FooFooFest/ArtsFest/Blue Angels Homecoming/Haunted Tours/Songwriters Fest.

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.

$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!

Sunset on the Bayou near NAS/Downtown Pensacola

If you’re looking for a quiet get-away on the water, you will find it here. Our cozy 2 bed/2 bath condo is like a cottage by the sea in a condo setting. Relaxing coastal decor and a beautiful view from the balcony make our home enjoyable inside and out. Enjoy all the amenities of home, sunbathe by the pool, fish from the dock, relax on the balcony, grill out on the lawn. Its all here. Just a short drive from Pensacola NAS, Pensacola Beach and historic Downtown Pensacola. (No pets allowed)

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of Mexico from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach! Nothing separates you from the best white-sand beach on the Gulf Coast. This beach condo boasts a vibrant interior filled with beach-themed accents, a private balcony with sweeping ocean views, and access to 2 pools (1 heated) and a hot tub. Enjoy the best restaurants and shopping on the beach, all within a short walk.

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.

Quiet & Cozy Family Home! Perfect Winter Stay!

Welcome to your quiet Pensacola getaway! The perfect home base for beach days, Blue Angels excitement, and relaxing evenings. Located in a peaceful neighborhood just minutes from Pensacola Beach, NAS Pensacola, and downtown, this clean and comfortable home is ideal for families, couples, military visitors, and longer winter stays. Whether you’re here for the sugar-white beaches, aviation events, or a laid-back escape, this home offers space, convenience, and comfort without the crowds.

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!

Sunny Large Two Bedroom Townhouse - Pool

Relax with our thorough cleaning, prioritizing your comfort. In a tranquil subdivision, Brookside offers a sunlit pool and tennis courts. The cozy living area guarantees a comfortable stay. 🌞 Pet-friendly with pre-approval, we welcome your furry friends. Only a 27-minute drive to white sandy beaches, enjoy a scenic 14-mile journey to Pensacola Beach or reach NAS Pensacola in 30 minutes. Don’t miss the breathtaking Blues fly every Sunday evening. Your ideal getaway awaits!

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.

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.