Holiday rentals with a pool in Pensacola

Private Pool-Near NAS-Grills-Game Room FamilySetUp

You have found a home that is loved by so many who come to Pensacola! This home offers so much for families: arcade room, 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 events as kite fest, wahoo games, bands on the beach, theater, Friday art nights and parades! BookNow

East Bay Hideaway — A Private Waterfront Escape

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

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.

Downtown Oasis - Pool & Parking

Centrally located in Pensacola's thriving downtown, our poolside oasis is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Full Kitchen, Washer & Dryer, Gas Grill, Garage, and Private Parking. Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. Enjoy your stay in America's first settlement and be sure to check out the VisitPensacola website for events while you're here!

Family Pool House! Airbnb's FAV Home! TOP 5%!

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, quick visits or longer 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.

Newly renovated condo with amazing water views!

Experience the clear blue water and white sand of Pensacola Beach. Enjoy spectacular views of Pensacola Bay from a private 3rd floor balcony. This newly renovated condo offers solid surface floors throughout, a fully stocked kitchen and calming beach decor. The master has a queen size bed, flat screen TV, and ensuite bathroom. The 2nd bedroom offers 2 full size bunk beds. The main living room has another flat screen TV, comfortable couch and is a perfect place for your group to gather.

Pensacola Blue Angel Pool House

Plenty of Space! Wonderful quiet home with a heated pool in a gated community on the outskirts of town. Located 20-25 min from Perdido Key and Pensacola beaches. The home is excellent for large groups or gatherings. The master bedroom is on one side of the house with all other bedrooms on the opposite side. The master bathroom has a garden tub for relaxing and a huge walk in closet. Outdoor patio is screened patio has an indoor firepit and plenty of games. We look forward to hosting you!

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.

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p

Welcome to The Diving Dolphin... a 2 bedroom/ 2 bathroom condo located in Emerald Isle Condominium complex~ Directly on Pensacola Beach! This beautiful condo is located on the 5th floor and overlooks the stunning waters of the Gulf of Mexico! Come on in and relax- this condo has it all! The condo has a capacity to comfortably sleep 6. We will send you a welcome packet with details about the complex, unit and area! ~COMPLIMENTARY BEACH CHAIR & UMBRELLA SET UP MARCH - OCTOBER!~

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!

Beautiful Paradise Home - 1 Mile From Beach - POOL

This two story home in Redfish Harbor provides a beach getaway in Perdido Key, Florida. Enjoy the many neighborhood amenities including a dock onto Bayou Garcon, a pool, pickle ball courts and a bocci ball court. This place is perfect for family vacations, a couples getaway or just some fun in the sun with friends. Let the spacious luxury of this home lull you into relaxation.

Relax Waterfront, Sunset VIEWS, Secluded Beach

Stunning 2-story unit, fully renovated, with plenty of space to accommodate up to 8 people. • Excellent LOCATION on the quite West end of Pensacola Beach. Last complex before National Park at Ft. Pickens • Gorgeous SUNSET views from both balconies • Just a few steps from the GULF OF MEXICO BEACH – perfect for couples and families! • QUIET AND SECLUDED Beach on Santa Rosa Sound