Vacation 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 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

The one-bedroom condo is located on Pensacola Beach in Tristan Towers. (The second bedroom is not accessible due to storage use.) Has an incredible view of the Gulf of Mexico and Pensacola Bay (wrap-around balcony). Located on the bay side, a short walk across the street allows easy access to white sand beaches and Gulf waters. The property has tennis courts, a swimming pool, and a pier. Shops, restaurants, and activities are nearby. Free trolley service runs from Memorial Day to Labor Day.

4.95 out of 5 average rating, 169 reviews

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.

Condo in Navarre Beach

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.

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, 212 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!

4.94 out of 5 average rating, 102 reviews

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.

Home in Pensacola

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!

An enclosed outdoor space features a heated saltwater pool surrounded by a safety fence. Metal chairs are positioned nearby on concrete flooring, providing comfortable seating. Soft sunlight illuminates the area, enhancing the tranquil setting.

4.93 out of 5 average rating, 106 reviews

Heated saltwater pool | Pet Friendly | Family home

Welcome to Whispering Sands, your ideal retreat for family relaxation. This centrally located Gulf Breeze oasis offers proximity to shopping, dining, the Gulf Islands National Seashore, and Pensacola Beach's pristine shores, all within a 10-minute drive. Step into a rejuvenated space adorned with new furnishings, flooring, and a fresh paint scheme. Bask in the serenity of the enclosed outdoor seating area or take a refreshing dip in the heated saltwater pool. Your tranquil escape awaits!

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: This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach that was voted BEST BEACH IN THE US! 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.

4.96 out of 5 average rating, 229 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.

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, 207 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.

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, 142 reviews

Beachfront Gulf View Oasis

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.

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, 110 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.

4.97 out of 5 average rating, 345 reviews

A heated pool is prominently featured in the foreground, surrounded by lounge chairs. In the background, the sandy beach leads to the Gulf of Mexico, with beach umbrellas and a fishing pier visible under a bright blue sky dotted with fluffy clouds.

Condo in Navarre Beach

2nd FLOceanFrontFreeChairsUmbrellaHeatedPoolArcade

Complimentary Daily Beach Service: (SEASONAL) Includes two chairs, one umbrella. Available 7 days a week, March 1st–Oct 31st (244 days annually) 9: 00 am – 5: 00 pm; Peak Season (Weather Permitting). Heated Pool: Yes, this condo provides a heated pool! Summerwinds Condo Complex heat’s one of the 3 pools every winter beginning the first day of Thanksgiving and turns off the first day of April.

Popular amenities for Gulf Breeze 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, 133 reviews

Home in Perdido Key

Sunny Side: Awesome Waterfront Unit with 4 Kayaks

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, 112 reviews

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

Superhost

A private pool is surrounded by a spacious patio, featuring palm trees and lush landscaping. The pool's clear water reflects the sky, while a nearby canal offers a serene view with docked boats in the distance.

Home in Navarre Beach

4.88 out of 5 average rating, 106 reviews

Beachie-Private Pool!

4.97 out of 5 average rating, 177 reviews

A wooden dock extends into calm waters, flanked by two covered structures in the distance. The scene is under a bright blue sky, adorned with fluffy white clouds, creating a serene atmosphere for fishing or relaxation.

Home in Navarre

East Bay Hideaway — A Private Waterfront Escape

4.99 out of 5 average rating, 127 reviews

Home in Pensacola

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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

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

4.93 out of 5 average rating, 219 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

4.99 out of 5 average rating, 73 reviews

Condo in Navarre Beach

Beach Gear Included - Walk to Beach - Sunset Views

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, 216 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

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, 134 reviews

Beachfront Condo • Pool & Resort Perks

4.91 out of 5 average rating, 111 reviews

Breathtaking Soundfront Condo|Pool & Beach Access!

4.96 out of 5 average rating, 167 reviews

A view of the resort-style pool is presented, with lounge chairs and umbrellas arranged around the water. Palm trees frame the scene, and the bright yellow exterior of a neighboring building adds vibrant color.

Condo in Perdido Key

Salt Shack at Purple Parrot, Perdido Key

4.96 out of 5 average rating, 212 reviews

A large outdoor pool is surrounded by palm trees and tropical landscaping, offering shaded seating areas under thatched roofs. The pool features a central island with rock formations, and the bright blue water reflects the clear sky above, creating a serene ambiance.

Condo in Perdido Key

This is the one! Perfect Getaway near the beach.

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.

4.93 out of 5 average rating, 28 reviews

Winter Waterfront Condo on Santa Rosa Sound | Walk

Other vacation rentals with a pool

4.96 out of 5 average rating, 83 reviews

A solar-powered swimming pool is enclosed within a netted structure, ensuring a bug-free environment. Colorful lounge chairs surround the pool, complemented by a shaded umbrella and a coffee table adorned with fresh flowers. Lush greenery is visible beyond the enclosure, enhancing the serene setting.

Home in Navarre

Covered Pool | Relax | 5 miles to Navarre Beach

A modern living area features a comfortable seating arrangement, including a spacious sofa and ottoman. Natural light floods in through large windows, offering stunning views of the water. A contemporary electric fireplace and shelving with decorative items add character to the space.

4.94 out of 5 average rating, 83 reviews

Pensacola Pearl

4.93 out of 5 average rating, 28 reviews

Emerald Isle 0201- 𝑺𝒂𝒍𝒕𝒘𝒂𝒕𝒆𝒓 𝑺𝒖𝒏𝒓𝒊𝒔

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, 26 reviews

Paradise on Pensacola Beach

Guesthouse in Pensacola Beach

A private balcony features two turquoise lounge chairs positioned to offer unobstructed views of the bay. Lush greenery frames the scene, which includes a fishing pier extending into the water. A clear sky and distant land contribute to the peaceful atmosphere.

5 out of 5 average rating, 59 reviews

Pensacola Beach Waterfront Condo

5 out of 5 average rating, 37 reviews

An inground pool is surrounded by a beige patio, with landscaped greenery providing a natural backdrop. The water is clear, reflecting the blue sky above. A pool cover is visible on the deck, and ample space allows for relaxation and sunbathing.

Home in East Hill

The Carriage House: relaxing stay with pool

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.