Holiday rentals with a pool in Pensacola Beach

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

A modern dining area features a round table with light-colored tableware, surrounded by four white upholstered chairs. Behind the table, a stylish shelving unit displays decorative items against a marbled wall. Expansive glass doors provide a view of the ocean and allow natural light to flood the space.

4.96 out of 5 average rating, 316 reviews

Phoenix X 1105- 1BR Florabama Beach Luxury Suite

This meticulously maintained and beautifully furnished Phoenix 10 condo is the epitome of elegance and sophisticated luxury for the discerning couple or small family seeking respite in a beach resort setting. Sip your morning coffee on your private balcony overlooking the beach and Gulf of Mexico. Situated directly on the beach! Parking available in Association lobby for a $60 fee per stay. Linens, towels and complementary starter package (TP/ paper towels, dish detergent and shampoo provided)

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.

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.

4.99 out of 5 average rating, 165 reviews

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

Townhouse in Navarre Beach

A spacious deck overlooks the calm waters of the Sound, framed by a clear blue sky. Two round, textured outdoor poufs are positioned near the railing, inviting relaxation while enjoying scenic views of the shoreline and distant piers.

4.97 out of 5 average rating, 122 reviews

Waterfront, beach, dock - your Salty Air Retreat!

Embrace island living in our little corner of paradise! This beautiful, family friendly home offers you the ultimate getaway with the clear, calm waters of the Sound right outside your door and the emerald green waters of the Gulf across the street. Swim, fish, and paddle board from your own backyard. Or just enjoy the view from your hammock as your kids build sandcastles on the private white sandy beach. Discover for yourself why Navarre Beach has been named "Florida's Most Relaxing Place"!

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, 128 reviews

Beachfront Condo With Pool & Resort Amenities

Welcome to Pensacola Perch, an 8th floor beachfront condo where you will enjoy expansive views of Pensacola Beach–– a perfect vantage point for dolphin sightings & the Blue Angels Air Show. This 2BR/2BA condo is in the sought after Emerald Isle gated resort where guests can enjoy resort amenities such as direct beach access, 2 swimming pools, a hot tub, sauna, & beachfront fitness center. There’s also complimentary use of 2 chairs & an umbrella from La Dolce Vita all through March to October.

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.

4.97 out of 5 average rating, 205 reviews

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

Perfect little place for couples or small families to get some R&R. This condo has a poolside view in a lovely little complex, and is just one building back from the beach - steps from paradise! The Gulf boasts some of the most beautiful beaches in the world, and this is the perfect location tucked away from the busy crowds but still close to restaurants, activities, live music, national parks, and a world class spa. The condo is well-equipped and recently updated in October 2022. Come enjoy!

A vibrant welcome sign featuring a flamingo and pineapples is displayed on the door. Inside, a spacious living area includes a white sofa, two black wire chairs adorned with colorful cushions, and a window dressed with sheer curtains, allowing natural light to fill the space.

4.96 out of 5 average rating, 175 reviews

The Flamingo Flat @ Villas on the Gulf

🦩Flamingo Flat: Ask about JAN/FEB longer stay discounts! This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach. For great shopping, dining & entertainment you can drive ( less than 3 miles West) to the main hub of P’Cola Beach. Trolley service available during summer months. The beautiful Portofino Island Resort is just 1 mile to the East. MUST BE 25 TO RENT. NO CHILDREN UNDER 12. NO PETS. EARLY CHECK IN MAY BE AVAILABLE FOR AN ADDITIONAL $50.

Apartment in Orange Beach

A seaside balcony offers a table surrounded by tall, teal chairs. The horizon meets the sparkling blue waters under a clear sky, reflecting sunlight on the surface. The scene invites moments of relaxation and enjoyment of the coastal views.

4.9 out of 5 average rating, 388 reviews

Beachfront - PENTHOUSE - Breathtaking 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.

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 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, 150 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!

This aerial view showcases the resort's dual swimming pools surrounded by lounge chairs. The heated pool is visibly larger and features curved edges. Beyond the pools, the white sandy beach and emerald waters of the Gulf are in view, with beach umbrellas lining the shore.

4.97 out of 5 average rating, 126 reviews

307 Beach Front Views ~ Special Rate ~ Book Jan 19

Come experience this Beautiful 5 Star Gulf Front Condo, Heated Gulf Side Pool & Hot tub, This Newly Renovated unit offers a Private, Gulf Front Balcony with Amazing Gulf Views, watch Dolphins, Swim in 2 Gulf Side pools, 1 heated, Hot tub on the Gulf. Sleeps 6, Gulf Front Balcony Master on Gulf, 2 BDRM, 2 BA, Master Suite has a luxurious King Size Cloud Lux Tempur-Pedic Bed. Guest Rm 2 has a Euro Top Plush Queen Mattress, LR has a Memory Foam Queen sleeper sofa.

Popular amenities for Pensacola Beach 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, 123 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

4.93 out of 5 average rating, 110 reviews

A screened-in pool area features a clear, blue pool surrounded by a spacious deck. Lounge chairs are positioned around the pool for relaxation. Lush palm trees and greenery are visible in the background, offering a glimpse of the outdoor environment.

Home in Pensacola Beach

Fun, sun, sand, and rest. Enjoy your stay with us.

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

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.

4.99 out of 5 average rating, 126 reviews

Home in Pensacola

Private Pool-Near NAS- Grills-Arcades-FamilySetUp

5 out of 5 average rating, 103 reviews

The private backyard features a fire pit surrounded by seating against a backdrop of palm trees and a moonlit sky. Soft lighting enhances the serene atmosphere, while a fence provides privacy. A hammock is visible in the distance, adding to the outdoor relaxation space.

Home in Orange Beach

Gameroom*Pool*Bikes*4 Arcades*Firepit*Ping Pong

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

4.95 out of 5 average rating, 160 reviews

A tranquil pool area is seen, featuring a clear blue swimming pool framed by a spacious deck. Palm trees dot the landscape, and a two-story building stands in the background. Comfortable seating options are present nearby, providing a relaxing outdoor atmosphere.

Home in Gulf Shores

Cabana, Pool, Fire Pit, 4 min walk to beach!

Apartment rentals with a pool

A spacious living area features large windows showcasing panoramic views of the ocean. Comfortable seating arrangements include a sectional sofa and armchairs, accompanied by a rustic dining table that seats six. A stylish chandelier hangs above, with a flat-screen television positioned on a wooden cabinet.

4.96 out of 5 average rating, 24 reviews

Sunrise to Sunset Views at Portofino 3-1301!

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, 214 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

An open living area features a modern design with a comfortable gray sofa and a light wooden coffee table. A dining table is visible in the background, accompanied by stylish chairs. A large wall-mounted TV is positioned above a white console cabinet, complementing the bright and inviting atmosphere.

4.95 out of 5 average rating, 39 reviews

The Lazy Luna | Family Friendly

Apartment in Fort Walton Beach

4.89 out of 5 average rating, 280 reviews

Okaloosa Island Oceanfront Paradise Studio Condo

4.97 out of 5 average rating, 138 reviews

A sandy beach stretches along the coastline, meeting gentle waves lapping at the shore. Sunbathers are scattered along the beach, with colorful umbrellas providing shade. In the distance, a pier extends into the water beneath a bright blue sky dotted with fluffy white clouds.

Apartment in Gulf Shores

*Beach Condo | Gulf Views | Family Favorite

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.

5 out of 5 average rating, 105 reviews

5 * Upscale Perdido Key, FL Waterfront Condo

Apartment in Fort Walton Beach

A bright studio room features a spacious bed with decorative pillows and a cozy blanket. A comfortable sofa is positioned nearby, and a small dining area is visible. Large sliding glass doors open to a balcony, allowing natural light to fill the space.

5 out of 5 average rating, 115 reviews

Waterfront cozy condo with king bed & resort pool

A vibrant, layered drink is served in a tall glass on a woven tray. The background features a sandy beach and tranquil turquoise waters under a clear blue sky, creating a relaxing coastal setting from the balcony.

4.99 out of 5 average rating, 165 reviews

Beach Front, Low Density Condo in Perdido Key!

Other holiday rentals with a pool

5 out of 5 average rating, 14 reviews

Beach Club #1404 'Pelican Pointe'

5 out of 5 average rating, 10 reviews

The exterior of the three-story beach home is showcased, featuring a large, inviting pool surrounded by lounge chairs. A spacious deck is visible, with the front of the house displaying double gables and multiple balconies. Lush landscaping is present around the pool area.

Home in Navarre Beach

Private Pool, Steps to the beach, Golf cart

5 out of 5 average rating, 7 reviews

Home in Navarre

Salt & Serenity | 3BR Coastal Island Escape

A bright living area features large glass doors that provide seamless access to panoramic ocean views. Comfortable seating is arranged around a light-toned sofa and stylish furniture. Natural light fills the space, highlighting the coastal decor and soothing color palette.

5 out of 5 average rating, 7 reviews

Sleeps 6-Stunning Ocean Front Views-Luxury Resort

4.94 out of 5 average rating, 17 reviews

A serene view of the waterfront at dusk is captured, showcasing a blend of warm sunset hues. Coastal homes are seen lining the shore, with palm trees dotting the landscape. A bridge is visible in the distance, adding to the tranquil atmosphere.

Apartment in Destin

WinterRetreat~PvtBeach~Heatedpool~HotTub~Resort

The living area features a light-colored, slipcovered sofa paired with a stylish chandelier above. A decorative console table holds elegant accessories, and large glass doors provide views of the Gulf, inviting natural light into the space.

5 out of 5 average rating, 32 reviews

A STEP ABOVE ! Stunning views on the 19th floor !

A spacious living area features large windows showcasing unobstructed views of the Gulf of Mexico. Comfortable seating arrangements include soft sofas and armchairs, complemented by a wooden coffee table. Natural light fills the room, creating a bright and airy atmosphere.

5 out of 5 average rating, 26 reviews

Gulf Front Views*Wraparound Balcony*Heated Pools!