Holiday rentals with a pool in Gulf Breeze

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)

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"!

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.

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

Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Townhouse in Navarre Beach

A balcony view is presented, featuring two light blue chairs positioned against a white railing. The landscape includes grass and shrubbery, leading towards a glimpse of water in the distance. Various structures are visible across the water, set against a clear sky.

4.91 out of 5 average rating, 197 reviews

Large Island Townhouse w/ View of Santa Rosa Sound

This 1500 sq. ft. townhouse is home away from home! On an island, it has access to Santa Rosa Sound & is across the street from Gulf of Mexico. Very comfortable w/ 2 bedrooms & 2.5 baths. It has a fully furnished kitchen & 3 balconies. Enjoy water views from main floor & master bedroom. An on-site swimming pool, pier w/ boat slips & beach frontage will meet water recreation needs. Has Direct TV. If you plan to be messy or not clean up after yourself, please don't rent my beach house.

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

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

Relax with family or friends at our cozy condo with amazing views of the bay and the Gulf of Mexico. You are mere steps from the gulf's famous sugar white sandy beaches. Enjoy the complex's amenities- sun at the private beach, swim in the pool (unheated), grill on the BBQ and chill at the fire pit. Rent bikes and explore the miles of beach paths and the Fort at Pickens. You're a short drive to the core of the beach where there's shopping, restaurants, bars and family activities.

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.

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

Experience the most beautiful beaches just steps away from your newly remodeled mid-century modern beach condo. The kids (big ones too) will enjoy the Arcade1up PAC-Mania and 70" Flat Screen TV. Our fun condo sleeps 6 comfortably with a King in the master bedroom and two queens in the second bedroom. All beds have brand new 5 star Zinus 12" mattresses, so you'll sleep like a baby:) You'll find the kitchen is fully stocked and ready to support all your cooking needs.

Popular amenities for Gulf Breeze 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

4.89 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

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.

4.93 out of 5 average rating, 110 reviews

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

A private heated pool is surrounded by a spacious stone deck, featuring several lounge chairs for relaxation. The pool is positioned under an elevated structure, allowing for shade and easy access. Tall palm trees frame the area, enhancing the tropical ambiance.

4.96 out of 5 average rating, 45 reviews

Heated Pool, Beach Gear, Direct Beach Access

Superhost

An inviting backyard features a fire pit surrounded by four wooden chairs, illuminated by soft string lights overhead. A swimming pool is visible in the background, complemented by lush greenery and a clear sky at dusk.

4.8 out of 5 average rating, 81 reviews

Balinese Beach House w/ Pool, Huge Hot Tub & Sauna

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.

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, 209 reviews

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.

Home in Pensacola

Flamingo On Fisher In The Heart Of Pensacola

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.

4.92 out of 5 average rating, 133 reviews

Sunset on the Bayou near NAS/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, 214 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

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

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, 12 reviews

Coastal Hideaway

A wide view of a pristine beach stretches under a clear blue sky, with soft sand marked by gentle footprints. Calm waves roll onto the shore, creating a serene atmosphere, while the horizon meets the water seamlessly.

4.91 out of 5 average rating, 111 reviews

Breathtaking Soundfront Condo|Pool & Beach Access!

4.96 out of 5 average rating, 160 reviews

Salt Shack at Purple Parrot, Perdido Key

Apartment in Navarre Beach

Aerial view of a serene beach featuring soft, white sands and clear turquoise waters. The coastline is framed by two tall buildings, set against a bright blue sky. The tranquil setting highlights the peaceful atmosphere of the Navarre Beach area.

4.96 out of 5 average rating, 191 reviews

Clean cozy Beachside Condo Snowbirds we want YOU!

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, 100 reviews

Book now for spring/summer! Beautiful sound views!

Other holiday rentals with a pool

Guest house in Pensacola Beach

A cozy studio apartment showcases a spacious bed against a white brick wall, accentuated by two pendant lights. A gray sofa is positioned nearby, accompanied by a textured throw pillow. A colorful rug adds warmth, while a framed artwork of a cow provides decorative interest.

4.85 out of 5 average rating, 55 reviews

Poolside Cabana

An outdoor pool is featured, surrounded by a spacious deck with lounge chairs positioned for sunbathing. Bright light reflects off the water's surface, and a clear blue sky complements the scene. A railing provides a barrier, offering views of the beach beyond.

5 out of 5 average rating, 24 reviews

Ocean Breeze East 802

5 out of 5 average rating, 11 reviews

Coastal Comfort~3BR~Pool~Sleeps 9~Pensacola Beach

The vibrant sunset over Sabine Bay is captured, with streaks of orange, pink, and blue reflected on the water's surface. Silhouettes of buildings stand against the colorful sky, and boats can be seen moored along the dock.

5 out of 5 average rating, 25 reviews

Paradise on Pensacola Beach

A well-maintained lawn extends towards a white picket fence bordering a sandy beach. Beyond the fence, the tranquil ocean sparkles under a clear blue sky. A lamp post stands near the edge of the lawn, providing illumination.

4.74 out of 5 average rating, 129 reviews

Beautiful beach views on ground floor

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, 21 reviews

A spacious bedroom is designed with large windows allowing natural light to fill the room. A king-sized bed is featured with a simple gray comforter and two accent pillows. A light area rug with a leaf pattern is positioned beneath the bed. Nightstands with lamps are placed on either side.

Flat in Pensacola Beach

Gulf Breeze Condo w/Pool Access!