Holiday rentals with a pool in Gulf Breeze

An aerial view showcases the townhome situated along the coastline, with the Gulf's waves gently breaking in the background. The neatly arranged buildings reflect a clean layout, while palm trees and a parking area are visible below, highlighting the nearby beach setting.

4.99 out of 5 average rating, 116 reviews

Spacious Townhome for Families w/ Beach+Bay Access

Come enjoy the very best of beach life! This Boardwalk townhome is steps from the famous white sand of the Gulf while also offering community pool access & a private, sandy beach on the calmer waters of the bay that is perfect for children to enjoy. This spacious 2 bed/2.5 bath unit (King in master!) has an open layout with beautiful furnishings & outdoor living space on all 3 levels. Plenty of natural light & some Gulf views from each of the balconies you can access from every room in the home.

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, 169 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.

5 out of 5 average rating, 175 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!

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.

When you stay at this centrally-located place, your family will be close to everything. The home is ranch-style and located on the canal in a fast-growing beachy community. Minimum stairs if you walk down to the canal. Take advantage of the local golf course which is minutes from the home. Enjoy the beautiful weather, shopping, and the local beaches (Navarre, Pensacola, and Destin) then come home to relax in your home away from home. We do not host parties or special events. Non smoking home.

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, 132 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, 208 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!

The image features a wooden pier extending into calm waters, leading towards a Bayfront condo complex with yellowish exteriors. Several boats are visible in the water, under a sky adorned with scattered clouds and soft blue hues.

4.92 out of 5 average rating, 120 reviews

Soul Shine - a Water Front Condo

Welcome to Soul Shine, a Bay front condo on Pensacola Beach. The perfect place for fun-in-the-sun, relaxation or family time. Enjoy spectacular views on our private balcony, a relaxed setting for morning coffee, dining alfresco, or afternoon sips with the dolphins! Soul Shine has access to a private pier+ the calm waters of Pensacola Bay, cool off in the pool or head to the emerald waters of the Gulf Coast across the street. Grill your fresh catch beachside or lounge by the fire pit.

Apartment in Orange Beach

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.

4.96 out of 5 average rating, 226 reviews

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.

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, 127 reviews

307 Beach Front Views ~ HUGE Special Book Mar 11

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.

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, 140 reviews

Stunning Gulf Views, Relaxing Family Beach Retreat

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, 192 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.

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, 107 reviews

Pensacola Beach Condo w/ Great Views (F12)

Perfectly situated on the quieter west end of Pensacola Beach this 3rd floor walk-up sits on the Pensacola Bay and is a 5 minute walk to the Gulf of Mexico. It’s our first season of hosting guests and we would love to have you. Our condo is less than 1/2 mile to Peg Leg Pete’s - a Pensacola Beach favorite restaurant. If you want a night-out, the Casino Beach and Boardwalk area has more than 10 restaurants and bars and is less than 2 miles away.

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 Relaxing Getaway

4.97 out of 5 average rating, 37 reviews

A newly renovated inground pool is featured, showcasing crystal-clear water under a bright sky. Two reclining lounge chairs are situated partially submerged for relaxation. A large umbrella provides shade beside the pool, and a surrounding grassy area is bordered by a wooden fence and tropical plants.

Home in Navarre

Sandy Toes and Tiki Flows

4.86 out of 5 average rating, 42 reviews

Home in Perdido Key

Beach Haven: Beautiful views, Kayaks, Pool & more!

Superhost

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.

4.86 out of 5 average rating, 98 reviews

Private (optional) Heated Pool King Beds-NearBeach

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

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

A sandy path leads through tall grass dunes toward the shimmering turquoise water of the Gulf. The bright sky overhead is dotted with light clouds, and a wooden sign stands at the entrance, indicating the path to the beach.

4.95 out of 5 average rating, 337 reviews

Quiet With views and a Gulf breeze

4.97 out of 5 average rating, 136 reviews

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.

Home in Pensacola

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, 214 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

A balcony view overlooks a tranquil sound with soft waves and clouds dotting the sky. Below, a private pool is nestled within a landscaped area, complete with lounge chairs. The beach extends gently along the shoreline, enhancing the relaxed coastal atmosphere.

4.96 out of 5 average rating, 228 reviews

Gulf Getaway+ Waterfront Views *Fully Updated*

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

The open living area features a dining table with four white chairs, a comfortable gray sofa, and a television mounted on the wall. Light enters through a window overlooking the sleeping area with a bed, enhancing the space’s relaxed atmosphere.

4.88 out of 5 average rating, 146 reviews

Footsteps away from beautiful beaches 🏖🏝⛱

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

4.96 out of 5 average rating, 116 reviews

Short Walk to Beach With a Pool!

A scenic view is presented, featuring a vibrant blue sky above a calm waterfront. A pool area is visible, surrounded by sun loungers. Lush palm trees and well-maintained lawns enhance the outdoor space, offering a relaxing atmosphere. Nearby buildings line the waterfront, adding to the picturesque setting.

4.84 out of 5 average rating, 229 reviews

Gorgeous Beach Condo

A modern kitchen is seen alongside a dining area with a table and stools. The open living space features a sofa and accent chair, with natural light filtering in from a large window. A cozy sleeping area is positioned in the background, adorned with soft decor.

4.88 out of 5 average rating, 329 reviews

The Sandy Secret

Other holiday rentals with a pool

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

An outdoor patio area features a large wooden table surrounded by several chairs. A private pool is visible nearby, with a fenced enclosure providing safety. Sunlight filters through the surrounding trees, creating a bright and inviting space for gatherings.

5 out of 5 average rating, 24 reviews

Casanana Beach Retreat- Beach Only 3 Miles Away!

4.96 out of 5 average rating, 45 reviews

Heated Pool, Direct Beach Access, Beach Gear

A screened pool area features a curved swimming pool and a separate hot tub with blue tile accents. Surrounding spaces include lounge chairs and a barrel sauna. Lush greenery and a wooden fence are visible in the background, creating a secluded atmosphere.

4.87 out of 5 average rating, 53 reviews

Casa Tranquilo Heated Pool and Sauna!

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

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

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 spacious balcony features a glass-top table surrounded by four high-back chairs, offering panoramic views of the Santa Rosa Sound. The ceiling fan enhances comfort while the inviting blue sky and gentle waves create a serene coastal setting.