Holiday rentals with a pool in 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, 225 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, 130 reviews

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

Guest suite in Gulf Breeze

A hammock is suspended under a shaded structure, positioned in view of a swimming pool. The pool's clear blue water reflects sunlight, surrounded by a privacy fence and lush greenery. Tall trees create a natural backdrop, enhancing the serene outdoor space.

4.9 out of 5 average rating, 237 reviews

East Bay Getaway - Studio with Pool & Hot Tub

Welcome to East Bay Getaway, a private studio nestled in the woods. This clean and comfortable room with private entrance is a MIL suite attached to your host's 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, with a large pool and hot tub in the shared, privacy fenced backyard. A bike/walk path is directly across the street, which goes for miles either direction. 3- burner BBQ grill - NEW for 25!

5 out of 5 average rating, 120 reviews

A custom upright piano converted into a bar is displayed, featuring blue lighting and an array of glassware. A colorful art piece hangs above the piano, alongside a unique lamp atop a wine barrel. The modern decor enhances the inviting atmosphere.

Home in Navarre

1.5 mi to Beach-New Pool! Smart home-Modern Decor!

Joey’s place is a beautiful home in Navarre, Florida, less than 1.5 miles to the beach with a newly added pool (not heated) in June 2024! You'll have the home to yourselves (office & master closet locked). Close to restaurants and shopping, modern décor, smart home, garage parking. Pool added in June 2024. Extended Patio added in September 2024, 8 ft privacy fence added in December 2024. Landscaping being added Spring into Summer 2025. Mural painting on fence surrounding pool Summer-Fall 2025

4.91 out of 5 average rating, 134 reviews

Bay Watch: Charming Waterfront Home with 2 Kayaks!

Welcome to Bay Watch! You'll enjoy gorgeous views, coffee on the balconies & serene waters. This unit sits on a calm, shallow cove of Perdido Bay, providing the perfect place for families to relax, play, and paddle safely. This 3 bed/2.5 bath comfortably sleeps 6 and includes a full kitchen, laundry room, and 2 kayaks! Spend all day right here, isolated and tucked away from the hustle and bustle. Or take a short 5 minute drive to Perdido Key Beaches, restaurants, etc. Continue for more Details

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, 109 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!

5 out of 5 average rating, 135 reviews

Pensacola Gem! Airbnb's Favorite 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.

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.

4.85 out of 5 average rating, 109 reviews

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!

4.96 out of 5 average rating, 240 reviews

A panoramic view of the beach and ocean is presented from the balcony. The water reflects light under a clear sky, while sandy beach stretches along the shoreline. Two bright blue Adirondack chairs are visible by a round table, offering a comfortable seating area for enjoying the surroundings.

Condo in Orange Beach

Beachfront Luxury Condo with Stunning Views

In the heart of Orange Beach is this luxury condo with gorgeous views of the sugar white beaches & emerald waters. From the balcony you can watch the majestic sunrise or marvel at the dolphins playing. When a break from the beach is needed you can enjoy the many amenities onsite. Orange Beach offers activities for the whole family including restaurants & shopping. After a fun day prepare to make dinner in the well appointed kitchen, relax with the cheerful decor & comfortable sitting.

5 out of 5 average rating, 215 reviews

A comfortable living area is shown with a large sectional sofa and a patterned chair. A round coffee table is centered in the space, complemented by a potted plant. Natural light enters through a window, while a wall-mounted TV displays a scenic beach image.

Townhouse in Pensacola

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.

A corner of the living area is presented with large windows offering expansive views of the water. A wooden desk and a light-colored chair provide a workspace, while a soft armchair and small table create a cozy seating arrangement. Natural light floods the space.

4.94 out of 5 average rating, 122 reviews

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

4.97 out of 5 average rating, 173 reviews

Townhouse in Perdido Key

Resort Living! 2 BD Townhome Perdido Key

Enjoy your stay in Perdido Key's Exclusive Lost Key Golf and Beach Club Resort Community which is nestled between Lost Key Golf Course and the Gulf of Mexico. Take advantage of the free beach shuttle service to the white sandy beaches and the private beach club. Gone Coastal Perdido provides the picture-perfect beach vacation where you will create a lifetime of memories...

Popular amenities for Pensacola rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 88 reviews

Home in Perdido Key

pirate ship•slide•rockwall•gameroom•ada•elevator

4.96 out of 5 average rating, 57 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

4.89 out of 5 average rating, 9 reviews

A private fenced pool is surrounded by a spacious patio area, featuring comfortable lounge chairs. Lush greenery is visible in the background, with a well-maintained yard offering ample space. Sunlight reflects off the clear water, creating a serene atmosphere for relaxation.

Home in Scenic Heights

Beautiful Pensacola Beach Home

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.

4.88 out of 5 average rating, 133 reviews

Beautiful Paradise Home - 1 Mile From Beach - POOL

5 out of 5 average rating, 18 reviews

Home in Navarre

The Palm Oasis | Heated Pool • Hot Tub • Beach

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.

4.94 out of 5 average rating, 211 reviews

Flamingo On Fisher In The Heart Of Pensacola

4.92 out of 5 average rating, 112 reviews

Home in Gulf Breeze

Heated saltwater pool | Pet Friendly | Family home

4.93 out of 5 average rating, 224 reviews

A private backyard features a heated pool surrounded by landscaped areas with palm trees and flowers. A covered porch provides shaded seating options, while lounge chairs invite relaxation by the water. A securely fenced area enhances safety and privacy.

Home in Navarre

Good times & tan lines! Only 5 miles to the beach!

Condo rentals with a pool

4.98 out of 5 average rating, 108 reviews

Two wooden lounge chairs are positioned on the sandy beach, facing the serene Gulf waters. Light fluffy clouds scatter across the clear blue sky, while gentle waves lap at the shore, creating a peaceful coastal scene.

Condo in Perdido Key

Marisol del Cielo/Sea Sun Of The Sky-On The Beach

4.93 out of 5 average rating, 137 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

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.

4.98 out of 5 average rating, 149 reviews

Relax at Our Gulf View Oasis

The living room features a cozy arrangement with a dark sofa and loveseat, complemented by a light coffee table. A wall-mounted TV is visible, alongside a sliding glass door that provides access to the private balcony. Tropical foliage can be seen through the glass doors.

4.88 out of 5 average rating, 147 reviews

Sugar Sand Beach Retreat at Villas on the Gulf

The living area features a comfortable gray sofa set, a white coffee table, and a ceiling fan. Natural light enters through sliding glass doors leading to a private patio. An open kitchen with wooden cabinetry and a dining area is visible, highlighted by bar stools at the counter.

4.96 out of 5 average rating, 228 reviews

$0 clean fee! Beachside/pool view/king bed/jacuzzi

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.

4.98 out of 5 average rating, 118 reviews

Pensacola Beach Condo w/ Great Views (F12)

4.95 out of 5 average rating, 182 reviews

Condo in Navarre Beach

La Playa Esmeralda - Panoramic Sunset Views

A dining area features a round table surrounded by six white, wooden chairs. The kitchen, equipped with updated stainless steel appliances, is visible in the background. Natural light enters through large windows, illuminating the space and enhancing the clean, modern design.

4.98 out of 5 average rating, 104 reviews

Book now for spring/summer! Beautiful sound views!

Other holiday rentals with a pool

A decorative knight statue stands beside a window, holding a shield marked with 'Round Table Resort'. Its silver armor is detailed with engravings, and the knight's visor partially covers its face. Green plants are placed near the base, enhancing the welcoming exterior.

5 out of 5 average rating, 62 reviews

Open Concept Coastal 5 Bed Heated* Pool/ Game Room

4.93 out of 5 average rating, 15 reviews

A modern three-story home is situated among lush greenery, visible under a vibrant sunset sky. Multiple balconies offer opportunities for outdoor enjoyment, while a driveway leads to a two-car garage. Palm trees and landscaped areas enhance the home’s welcoming appearance.

Home in Perdido Key

Walk/Bike/Golf Cart to Beach | Luxury Home w/Pool

A balcony space features a hanging chair and a small side table, surrounded by decorative lattice railing. The sun sets in the background, casting a warm glow over the calm water and buildings lining the shore.

5 out of 5 average rating, 37 reviews

Sea-Sun's Greetings • Pensacola Beach • 2BR Condo

4.74 out of 5 average rating, 35 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

4.93 out of 5 average rating, 15 reviews

A vibrant living area features a comfortable sofa adorned with pillows in various shades of blue. A wall mural with tropical leaves and a sun motif adds a lively touch. The open layout provides a view of the modern kitchen in the background.

Home in Gulf Breeze

Pensacola Backyard Oasis

4.83 out of 5 average rating, 6 reviews

An open concept living area is highlighted, featuring a modern kitchen with stainless-steel appliances and granite countertops. A dining area with a wooden table is visible, along with a cozy seating arrangement including a sofa and coffee table. Ample natural light floods the space from the nearby windows.

Townhouse in Pensacola

Downtown Townhome l Pool l Quiet & Family Friendly

4.95 out of 5 average rating, 78 reviews

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A coffee table sits in front, accompanied by small potted plants. Natural light filters in through large windows, while a dining area and a kitchen bar with stools are visible in the background.

Townhouse in Pensacola

Elegant townhome + oversized luxury pool