Holiday rentals with a pool in Pensacola Bay

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.

4.92 out of 5 average rating, 106 reviews

Hot tub/ Pool at this Relaxing Getaway

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!

4.99 out of 5 average rating, 136 reviews

A bright living area offers views of the Gulf through expansive glass doors. The space features comfortable seating, including wicker chairs and a cozy sofa. A telescope stands nearby for observing the shoreline, while a balcony with seating is visible beyond.

Condo in Pensacola Beach

Heated Pool + Sunsets | Modern Beach Escape

TWO Gulf-View Balconies | Heated Pool | Gulf & Sound Beach Access | King Primary Suite • Unobstructed Gulf Views from two private balconies • Heated Pool for cool weather swimming • Direct Beach Access – just steps to sugar-white sand • Primary King Suite with spa-like ensuite • Beach Gear Included – chairs, wagon & umbrella • Jacuzzi Tub for ultimate relaxation • Fully Equipped Chef’s Kitchen + Wet Bar with Ice Maker • 65" Smart TV with Sonos Surround Sound • Gated Community with Covered Parki

4.99 out of 5 average rating, 114 reviews

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 Gulf Breeze

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.

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.

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.

4.89 out of 5 average rating, 121 reviews

Sunny Side: Awesome Waterfront Unit with 4 Kayaks

Welcome to Sunny Side! Come enjoy fun and relaxation right outside your back door! Sitting on a calm, shallow cove of Perdido Bay, Sunny Side provides the perfect place for families to swim and play safely. This 2 bed/2.5 bath sleeps 7 people across 4 different beds and includes a full kitchen, laundry, 4 Kayaks, and more! Spend all day here, tucked away from the hustle and bustle, or take a short 5 minute drive to Perdido Key Beach, restaurants, parks, and more! Continue for more Details

4.92 out of 5 average rating, 131 reviews

A serene waterfront view at sunset features a serene bay with multiple sailboats and yachts docked. The sky is painted in soft shades of pink and purple, reflecting on the calm water. A grassy area with kayaks and canoes is visible in the foreground.

Condo in Pensacola

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)

4.98 out of 5 average rating, 209 reviews

A private balcony offers sweeping views of the Gulf of Mexico, showcasing the clear blue waters and soft sandy beach below. The horizon merges sky and sea, creating a serene coastal scene. Beach chairs and umbrellas are positioned along the shoreline, inviting relaxation.

Condo in Pensacola Beach

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.

4.96 out of 5 average rating, 130 reviews

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

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”!

5 out of 5 average rating, 174 reviews

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 Pensacola

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!

4.97 out of 5 average rating, 163 reviews

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

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.

4.93 out of 5 average rating, 110 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!