Holiday rentals with a pool in Downtown Pensacola

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.

4.98 out of 5 average rating, 217 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of America from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach, named America’s Best Beach by the Condé Nast Traveler Readers’ Choice Awards! 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.

4.99 out of 5 average rating, 127 reviews

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 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

5 out of 5 average rating, 176 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.

Guest house in East Hill

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!

Home in Downtown Pensacola

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, 218 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.

A well-furnished living area is depicted, featuring two patterned armchairs and a sectional sofa. A coffee table is centered on a vibrant area rug, while a large flat-screen television is mounted on the wall. Natural light fills the space through a glass door leading to the outside.

4.94 out of 5 average rating, 102 reviews

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!

A serene backyard space features a clear blue pool surrounded by lush greenery. Sunlight filters through the trees, and a variety of plants decorate the perimeter. Lounge chairs are positioned near the pool, providing a comfortable area to relax and enjoy the outdoors.

4.95 out of 5 average rating, 209 reviews

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.

4.91 out of 5 average rating, 140 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”!

An aerial view captures a family-friendly home nestled in a spacious yard with lush greenery. A private, crystal-clear pool is seen in the backyard, surrounded by patio space. The property is bordered by a fenced area, providing a sense of seclusion and tranquility.

5 out of 5 average rating, 125 reviews

Pensacola Gem! Airbnb's Favorite Home! TOP 10%!

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.

A balcony overlooks the Gulf of Mexico, featuring two red chairs positioned for seaside relaxation. The horizon reflects sunlight, and sandy beach chairs are visible below along the shoreline, creating a serene oceanfront view.

4.93 out of 5 average rating, 152 reviews

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!

4.94 out of 5 average rating, 186 reviews

A bright living area features a comfortable seating arrangement and a wooden dining table for four. Large windows provide views of the beach, allowing natural light to fill the space. A flat-screen TV is mounted on the wall, complemented by beach-themed decor and soft furnishings.

Apartment in Perdido Key

Serving Vitamin SEA! Ground floor BEACHFRONT views

Welcome to Perdido Skye!! Our property location is 13785 Perdido Key Dr. Pensacola, FL, 32507. Unit G1. We fell in love with this ground floor, cozy condo with views that connect you to the sugar-white sand beaches and sparkling blue gulf waters. Our corner unit fills the rooms with sunshine and lots of Vitamin SEA and is very accessible to the pool, ocean, grilling area and parking. No hassle or waiting for elevators. HAPPY BEACHING!! Sincerely, Steven and Rebekah

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.

4.99 out of 5 average rating, 142 reviews

Beachfront Gulf View Oasis

TWO Gulf-View Balconies • Heated Pool • Gulf & Sound Access • King Suite • Family-Friendly Escape to our spacious 3-level Pensacola Beach condo for 8! Enjoy Gulf views from two private balconies, direct beachfront access, and a heated community pool. This waterfront retreat features a chef's kitchen, a primary suite with a Jacuzzi, and a fun bunk room. Perfect for families seeking a serene coastal getaway with modern comforts and a prime location near Fort Pickens.

4.98 out of 5 average rating, 194 reviews

A spacious outdoor area is enclosed with a framed structure, featuring soft blue and white lighting along the floor. Potted plants add a touch of greenery, while lounge chairs are neatly arranged within the space, providing a relaxing ambiance for outdoor gatherings.

Tiny home in Pensacola

Tiny Home Pool View 25 Mins to Beacha

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 in the backyard located 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.

Popular amenities for Downtown Pensacola rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 125 reviews

A community pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are arranged neatly along the edge, and two pavilions with covered seating are visible. Lush greenery and a clear blue sky create a serene setting.

Home in Perdido Key

Beautiful Paradise Home - 1 Mile From Beach - POOL

Home in East Pensacola Heights

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.

4.93 out of 5 average rating, 107 reviews

Hot tub/ Pool Relaxing Getaway

4.94 out of 5 average rating, 31 reviews

Two blue kayaks are positioned on a grassy area near calm waters, reflecting the soft colors of the sky. The dock is visible in the background, surrounded by trees, creating a peaceful waterfront scene.

Home in Gulf Breeze

Cozy Bay Front | Fire Pit, Kayaks, Sunsets

4.93 out of 5 average rating, 118 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

A spacious single-story home features a blend of stone and siding, surrounded by a manicured lawn. The entrance is marked by a wide porch, complemented by large windows and shutters on either side. A driveway leads toward the garage on the left.

4.86 out of 5 average rating, 105 reviews

Pensacola Blue Angel Pool House

4.86 out of 5 average rating, 99 reviews

A clear blue pool is captured with a decorative waterfall feature, creating gentle ripples in the water. Stone accents surround the pool, enhancing the serene atmosphere. A seating area is visible in the background, framed by the textured exterior of the house.

Home in Pensacola Beach

Private (optional) Heated Pool King Beds-NearBeach

4.88 out of 5 average rating, 99 reviews

A spacious living room is furnished with a large sectional sofa and a matching ottoman, set atop a decorative area rug. Natural light is provided by windows, with ceiling fans enhancing the comfortable atmosphere.

Home in Sanders Beach

Private Pool / Two living rooms /Downtown

4.95 out of 5 average rating, 337 reviews

Home in Pensacola Beach

Condo on Pensacola Beach

Apartment rentals with a pool

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.

4.93 out of 5 average rating, 134 reviews

Sunset on the Bayou near NAS/Downtown Pensacola

A spacious living area features multiple seating options, including a sofa set and armchairs, with panoramic views of the Gulf visible through floor-to-ceiling windows. Natural light illuminates the room, which has light-colored flooring and a decorative area rug, creating a comfortable and airy atmosphere.

5 out of 5 average rating, 14 reviews

Gorgeous! Modern decor! Holiday Specials!

An aerial view captures the Sabine Yacht and Raquet Club, a multi-story building situated near the sandy beach. The Gulf of Mexico's blue waters stretch out beyond the shore. Surrounding areas include a tennis court, a swimming pool, and a boat dock along the coastline.

4.9 out of 5 average rating, 77 reviews

Beautiful Gulf View Waterfront Condo

4.86 out of 5 average rating, 36 reviews

Apartment in Perdido Key

Windemere 1204-Beachfront Views and Pool

A wrap-around balcony offers a panoramic view of the Gulf of Mexico and nearby homes with varied roof designs. A gently sloping shoreline leads to the water, while the sky displays soft hues, suggesting evening light. The surrounding area is characterized by green spaces and pathways.

4.89 out of 5 average rating, 102 reviews

Pensacola Beach, Florida 1BR Amazing View

A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.

4.99 out of 5 average rating, 134 reviews

Beachfront Condo • Pool & Resort Perks

An aerial view of Gulf Breeze shows a blend of residential buildings and green landscapes. The expansive blue bay stretches into the distance, with bridges connecting the land on both sides. Parking areas and lush trees can be seen throughout the community.

5 out of 5 average rating, 13 reviews

Coastal Hideaway

A serene view of the bay is captured from the balcony, showcasing the calm water and sandy beach lined with outdoor furniture. In the distance, a pier extends into the water, while boats can be seen sailing peacefully, framed by the clear blue sky.

4.99 out of 5 average rating, 110 reviews

Pensacola Beach Condo w/ Great Views (F12)

Other holiday rentals with a pool

A private balcony features a round table surrounded by four wicker chairs, offering sweeping views of the Gulf of Mexico. The tranquil blue waters and clear sky create a serene backdrop for outdoor relaxation.

4.7 out of 5 average rating, 47 reviews

EI 303 2B Gulf Front w/ Spectacular Views!

5 out of 5 average rating, 13 reviews

Great Location with Relaxing Pool

4.96 out of 5 average rating, 50 reviews

The outdoor space features a heated pool, accompanied by three illuminated spheres on the water's surface. Comfortable loungers and a dining table with chairs are positioned around the area, while an umbrella offers shade. A wall-mounted TV is visible under the covered patio.

Home in Sanders Beach

Luxury Heated Pool Home 8Beds 2.5BA 15min To Beach

5 out of 5 average rating, 78 reviews

An electric golf cart with seating for six is parked in front of the townhouse alongside four adult bicycles in various colors. The grassy area provides a friendly outdoor space, complementing the inviting entrance of the property.

Townhouse in Perdido Key

*Eagle's Landing* | Self-Managed | Private Beach

4.72 out of 5 average rating, 32 reviews

An open-concept living space is featured, showcasing a spacious sectional sofa and a decorative circular coffee table. Natural light shines through large windows, while a potted plant adds a touch of greenery. The dining area, equipped with bar stools, is visible in the background alongside a modern kitchen.

Villa in Perdido Key

Hale Piko, Lost Key Golf and Beach Resort NEW

Guest house in Pensacola Beach

5 out of 5 average rating, 11 reviews

Gulf Breeze Bungalow

4.93 out of 5 average rating, 76 reviews

An outdoor patio is shown, featuring a fire pit surrounded by comfortable seating. A swimming pool is visible in the background, with lush greenery framing the area. The evening sky creates a serene ambiance, complemented by the flickering flames from the fire pit.

Guest suite in Pensacola

Private Suite with Saltwater pool