Holiday rentals with a pool in Ensley

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, 139 reviews

Quiet Lux Family Beach Retreat

TWO Gulf-View Balconies • Heated Pool • Gulf & Sound Access • King Suite • Family-Friendly Enjoy a waterfront Pensacola Beach condo with stunning Gulf views and direct beach access. This spacious 3-level vacation rental sleeps 8 and features two private Gulf-view balconies, a chef’s kitchen, and a bright solarium. Walk to both Gulf and Sound beaches or relax by the heated community pool. Quiet Fort Pickens location with easy access to dining, attractions, and the free island trolley—perfect for

Superhost

An open-plan living area features a light-colored sofa with decorative cushions, two armchairs, and a round coffee table. A dining table with seating for six and a fully equipped kitchen are visible in the background. Natural light brightens the space through large windows.

4.75 out of 5 average rating, 193 reviews

New Townhome! near Downtown and Pensacola Beach

Welcome to this brand new luxury townhome perfect for that get-away you've been trying to plan! Only a short drive away from downtown (15 min), Pensacola Beach (25 min), and conveniently near Publix, restaurants, retail and the interstate makes this the perfect place for you to come enjoy everything beautiful Pensacola has to offer. This townhome features a fully equipped kitchen, gameroom, an open floor plan, community pool, washer&dryer and it's just a short walk away from the community pool.

Apartment in Navarre Beach

A cozy bedroom features a spacious bed covered in a light blue quilt. Two matching pillows are positioned at the head of the bed. A large window offers views of the surrounding landscape, with a picture of a coastal scene displayed above the bed.

4.95 out of 5 average rating, 168 reviews

La Playa Esmeralda - Panoramic Sunset Views

Welcome to La Playa Esmeralda, a beautifully renovated 2nd floor studio. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 2 comfortable beds-1 regular and 1 Murphy bed, along with a coffee bar and fully equipped kitchen. You're just a 5 minute walk to the beach. Enjoy a dip in the pool, grilling in the gazebo and fish all night long on our large, private fishing pier, no fishing license required. Early check-in avail.

4.99 out of 5 average rating, 165 reviews

A bright living area features a spacious white sectional sofa adjacent to a light wood coffee table. Floor-to-ceiling glass doors offer expansive views of the ocean and sky, enhancing the openness of the space. A dining set is visible on the balcony.

Apartment in Perdido Key

MELODY OF THE SEA - ON THE BEACH- INCREDIBLE VIEWS

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! Beautifully remodeled and updated! This retreat has the rare double windows to enjoy stunning panoramic sunset views! On the beach (No roads to cross)! Resort has indoor heated pool & outdoor pool & hot tub overlooking the ocean. 2 fireplaces in the living room bedroom for those cozy mild winters. King size bed in the master... nautical bunkbeds with port holes & queen sleeper sofa in the main living areas. Reserve Your Time Away Today

4.94 out of 5 average rating, 211 reviews

A modern retreat is showcased with a striking dark exterior and large glass windows. The wooden deck is complemented by outdoor seating, while lush greenery surrounds the home, creating a serene setting within the pine forest.

Home in Pace

The Pine House Pace, FL

Enjoy this UNIQUE retreat! Located on 3 acres of lush pines, this home is the perfect getaway for you or your family. With the romantic modern vibe of the house, you are sure to feel RELAXED, REJUVENATED and ready for whatever is next. Cool the day off in our backyard SITTING POOL, or read a book in our 7 ft SITTING WINDOW. Watch the pines sway through our living room observing windows or have friends over for dinner at our outdoor dining area! No matter the reason, the Pine House is for you!

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.

4.92 out of 5 average rating, 133 reviews

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)

4.91 out of 5 average rating, 104 reviews

A living area is displayed, featuring a comfortable gray sofa with decorative yellow pillows. A set of nested coffee tables sits in front, with a simplistic design. A wall-mounted television and a decorative fireplace are visible, while natural light filters through a window adorned with light curtains.

Apartment in Pensacola

Stylish 1 bdrm condo. May sleep 4. Just off I10

Enjoy easy access to everything from this perfectly located home base. Totally refurbished. All new appliances and furniture, microwave, dishwasher, washer and dryer, and various utensils. Toiletries initially supplied. Close to shopping malls, restaurants and fast food outlets. Beautiful Pensacola Bch just 20 mins away. Downtown 15 mins NAS 15 mins Airport 10 mins Hospitals 5 mins Check in after 2 p.m. Check out 11 a.m. Pool key provided but must be returned Perfect for work or leisure

5 out of 5 average rating, 123 reviews

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.

4.96 out of 5 average rating, 135 reviews

A screened balcony features two light-colored seating chairs and a coffee table, offering a view of the waterway. Tall buildings are visible in the background, and a plush blue area rug enhances the inviting space.

Townhouse in Perdido Key

Winter Discounts! Lost Key 3BR Beach & Golf Stay

SNOWBIRDS — WE WANT YOU THIS WINTER! ❄️➡️☀️ Escape the cold! Enjoy discounted, flat monthly rates at “Family Tides,” in Lost Key Beach & Golf Resort This 3 BR/2.5 BA townhome offers: ✔️Gulf views ✔️Resort pools ✔️Private beach club access ✔️5-min walk or complimentary shuttle to the sand Fully stocked kitchen, fast Wi-Fi, washer/dryer, garage parking, & beach gear - all you need for a comfortable long-term stay Perfect for snowbirds seeking sunshine near Pensacola & Perdido Key

A spacious living area is presented with a cozy sectional sofa, accent chairs, and a decorative coffee table. A large TV is mounted on a serene white console. Natural light filters through sliding glass doors, revealing views of the outdoor greenery.

4.87 out of 5 average rating, 141 reviews

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!

4.98 out of 5 average rating, 187 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.

4.89 out of 5 average rating, 122 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

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.

Popular amenities for Ensley rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a 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 at this Relaxing Getaway

4.93 out of 5 average rating, 117 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

4.97 out of 5 average rating, 175 reviews

A spacious screened pool area is showcased, featuring a sparkling blue pool with a shallow entry. Surrounding the pool are lush green trees and a view of the bay, creating a serene backdrop that invites relaxation.

Home in Navarre

East Bay Hideaway - Sun. Swim. Sunset. Stargaze.

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, 104 reviews

Pensacola Blue Angel Pool House

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, 216 reviews

Historic Downtown Bayfront Home Pool Mins to Beach

An outdoor area features a hot tub alongside a round stock tank pool, each inviting relaxation. A colorful beach ball floats in the stock tank pool. A lounge chair is placed next to the hot tub, surrounded by green grass and gravel.

4.94 out of 5 average rating, 65 reviews

Amazing Hot Tub/ Stock Tank Pool

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

An outdoor pool area is enclosed by a screened patio, featuring a rectangular pool and a hammock for relaxation. Comfortable seating is arranged around a coffee table, with greenery adding a touch of nature. A bar with stools is visible, enhancing the outdoor experience.

4.97 out of 5 average rating, 132 reviews

Poolside Retreat, Hot Tub, 5 min to beach

Apartment rentals with a pool

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, 213 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

A bright waterfront scene is captured, featuring Little Sabine Bay with reflections shimmering on the water's surface. The view includes marinas with sailboats and yachts, framed by palm trees and gardens, with a pool visible in the foreground.

5 out of 5 average rating, 144 reviews

Stay at Sunshine Daydream on Pensacola Beach

Apartment in Orange Beach

A cozy living area is furnished with a sofa and an armchair, complemented by wall decorations and soft lighting. A sliding glass door offers access to a balcony, while a compact kitchen area features bar seating. Bright curtains frame the windows, allowing natural light to fill the space.

4.91 out of 5 average rating, 194 reviews

Lei Lani Life, Live it, Love it!

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, 105 reviews

Pensacola Beach Condo w/ Great Views (F12)

The living area features a leather sofa adorned with colorful cushions, complemented by a glass coffee table. A ceiling fan with leaf-shaped blades hangs above, while large windows are framed by bright yellow curtains. A potted plant adds a touch of greenery to the space.

4.92 out of 5 average rating, 203 reviews

Fun Mid-Century Modern Beachside Condo on the Gulf

4.96 out of 5 average rating, 159 reviews

Apartment in Perdido Key

Salt Shack at Purple Parrot, Perdido Key

5 out of 5 average rating, 105 reviews

An aerial view of a coastal vacation home is displayed, showing its modern six-story structure set amidst lush greenery. The expansive parking lot accommodates numerous vehicles, with tennis courts visible nearby. The landscape features both the coastline and the Intracoastal Waterway, highlighting the location's natural beauty.

Apartment in Perdido Key

5 * Upscale Perdido Key, FL Waterfront Condo

Superhost

A balcony with a circular table surrounded by four plastic chairs features a view of the bay. The scene includes grassy areas and nearby buildings, with palm trees visible in the background under a partly cloudy sky.

4.8 out of 5 average rating, 130 reviews

Bliss on the Bay 2BR 2BA Beach Condo with Pool D7

Other holiday rentals with a pool

A comfortable living area features a gray sofa adorned with patterned throw pillows. A round coffee table sits in front of the sofa, while a modern workspace with a chair is positioned nearby. The kitchen is visible in the background, showcasing white cabinetry and a spacious layout.

4.96 out of 5 average rating, 26 reviews

Minutes from white sand and blue seas! 3BR/2.5BA

An open layout features a well-lit living area with a spacious gray couch and decorative pillows. A dining table is visible alongside a modern kitchen with granite countertops and stainless steel appliances. Large windows allow natural light to fill the space, creating a bright and welcoming atmosphere.

4.73 out of 5 average rating, 41 reviews

Home near I-10 with Pool! Late checkout!

A sunlit living room features a full-size sofa and two accent chairs, complemented by a large Smart TV mounted on the wall. Sliding glass doors open to a balcony offering bay views, with natural light filtering through the beige curtains.

5 out of 5 average rating, 41 reviews

Baywatch Retreat 2/2 Beach Condo w/Pool

A spacious pool is surrounded by a brick patio and lush greenery. A gazebo with a distinctive metal roof is visible in the background, providing a shaded area near the water. A slide is positioned at the pool's edge, inviting recreational use.

4.96 out of 5 average rating, 56 reviews

Peaceful Pensacola Paradise

4.88 out of 5 average rating, 97 reviews

Apartment in Pensacola

Perfect for Long Stays • Modern & Cozy 2BR

5 out of 5 average rating, 24 reviews

An adventurous putt-putt golf course is framed by colorful borders in vibrant pink and blue. The course features multiple holes laid out on a lush green surface, surrounded by decorative mulch and plants, with string lights hanging overhead, enhancing the playful atmosphere.

Home in Pensacola Beach

Golfing Bear

A screened-in swimming pool area features clear blue water, with lounge chairs positioned nearby. Sunlight reflects off the water's surface, and a grassy lawn surrounds the pool area. The house is visible in the background, providing additional context to the outdoor space.

4.81 out of 5 average rating, 52 reviews

Cozy 5br Pool House by I-10 and the Beach

A dynamic aerial display features six military jets creating vapor trails against a clear blue sky. Below, a sandy beach runs alongside a vibrant turquoise shoreline, with buildings visible in the background. The scene captures a moment of excitement and movement over a coastal view.