Vacation rentals with a pool in Pensacola

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.

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.

Guesthouse 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!

4.99 out of 5 average rating, 127 reviews

Private Pool-Near NAS- Grills-Arcades-FamilySetUp

You have found a home that is loved by so many who come to Pensacola! This home offers so much for families: arcade games, board games, foosball coffee table, cards, the pool, it's full of fun! Guests rave about how clean it is, that pics are accurate & how quiet the neighborhood is yet a simple drive to restaurants, attractions and the beaches. Great for visiting military at NAS/Corry station or fall events as The Fair/FooFooFest/ArtsFest/Blue Angels Homecoming/Haunted Tours/Songwriters Fest.

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"!

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

The Bayfront Manor brings the best of both worlds to your vacation or business stay in Pensacola. Located 5 min walk from historic downtown, Seville Square, and Palafox Street, the location is ideal for all dining, nightlife, and events. The home is positioned on the corner of Bayfront Dr allowing for great water views of Pensacola Bay. The best beaches on the Gulf are only a 10 min drive. The location is also great for wedding parties as the Barkley House and Christ Church are walkable.

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.

4.94 out of 5 average rating, 102 reviews

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!

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, 152 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!

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.

4.97 out of 5 average rating, 180 reviews

The image captures the nighttime view of a screened-in pool area, illuminated by blue lights. The architectural structure showcases a modern design, with clear visibility of the surrounding landscape featuring trees and grassy grounds. Soft lighting enhances the atmosphere, suggesting a serene outdoor space.

Tiny home in Pensacola

Tiny Home Pool View 25 Mins to Beachb

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 located in the backyard 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.

5 out of 5 average rating, 206 reviews

A comfortable living area is shown with a large sectional sofa and a patterned chair. A round coffee table is centered in the space, complemented by a potted plant. Natural light enters through a window, while a wall-mounted TV displays a scenic beach image.

Townhouse in Pensacola

Stylish Modern Retreat in Downtown + Pool

It's all about the location! This comfortable, spacious townhome is the perfect home base for all your Pensacola adventures. Enjoy the many activities close by: Pensacola Beach (10 miles), Perdido Beach & Johnson's Beach (15 miles), boat charters and fishing, fine dining and pubs, museums, Blue Angel air shows, festivals, Wahoo baseball etc. Or spend the day relaxing at the beautiful pool. Book now to enjoy all the amenities and comforts this home offers.

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.

4.96 out of 5 average rating, 167 reviews

Salt Shack at Purple Parrot, Perdido Key

The Salt Shack condo is located within the Purple Parrot Village Resort, which is about 1/2 mile from the white sandy beach of Perdido Key! The UPSTAIRS condo's rear terrace overlooks the outdoor resort style pool/hot tub! This vacation home has a king size bed in the bedroom and set of built-in bunk beds in the living room which allows it to sleep up to 4 guests. Other amenities include a heated indoor pool/hot tub, fitness center and saunas.

A corner of the living area is presented with large windows offering expansive views of the water. A wooden desk and a light-colored chair provide a workspace, while a soft armchair and small table create a cozy seating arrangement. Natural light floods the space.

4.94 out of 5 average rating, 111 reviews

Relax Waterfront, Sunset VIEWS, Secluded Beach

Stunning 2-story unit, fully renovated, with plenty of space to accommodate up to 8 people. • Excellent LOCATION on the quite West end of Pensacola Beach. Last complex before National Park at Ft. Pickens • Gorgeous SUNSET views from both balconies • Just a few steps from the GULF OF MEXICO BEACH – perfect for couples and families! • QUIET AND SECLUDED Beach on Santa Rosa Sound

Popular amenities for Pensacola 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

4.94 out of 5 average rating, 212 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, 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

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

4.93 out of 5 average rating, 106 reviews

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.

Home in Pensacola Beach

Heated saltwater pool | Pet Friendly | Family home

4.95 out of 5 average rating, 337 reviews

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.

Home in Pensacola Beach

Quiet With views and a Gulf breeze

5 out of 5 average rating, 20 reviews

Adventures at Gypsy Mermaid

5 out of 5 average rating, 125 reviews

Pensacola Gem! Airbnb's Favorite Home! TOP 10%!

Condo rentals with a pool

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, 26 reviews

Ocean Breeze East 802

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, 42 reviews

The Lazy Luna | Family Friendly

A wooden walkway leads directly to the beach, bordered by tall palm trees and coastal vegetation. The path is flanked by wooden railings, providing a clear route to the shoreline while showcasing the open sky and distant waves in view.

4.85 out of 5 average rating, 195 reviews

Perdido Key Florida. Grand Caribbean East 2 BR 2BA

The two-story unit is presented in a peach-colored exterior with a green metal roof. A balcony is visible on the second floor, framed by white railings. A golf cart is parked in front, and a sign indicates golf cart access only. Lush greenery surrounds the building.

4.88 out of 5 average rating, 219 reviews

Island Resort Cottage in Perdido Key

A bright living area features a spacious sectional couch facing a large flat-screen TV mounted on the wall. Natural light fills the space through expansive windows that offer views of the Gulf. Two round mirrors add depth, and a small table rests on a soft rug.

5 out of 5 average rating, 14 reviews

Palm Beach Club #230 @DEEbeach | Pool + Walk2Beach

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!

A private balcony showcases a round table surrounded by four chairs, overlooking a serene beach. The ocean glistens under a bright sky, with gentle waves lapping at the shore. A sandy beach stretches out in the distance, inviting leisurely strolls.

5 out of 5 average rating, 6 reviews

Perdido Sun #404 on the Beach!

Superhost

A large balcony offers unobstructed views of the Gulf of Mexico, showcasing vibrant blue waters and a sandy shoreline. The clear sky extends above, while the railing provides a safety barrier. Seating is positioned for relaxation and enjoyment of the expansive landscape.

5 out of 5 average rating, 3 reviews

12th floor unit-Fabulous direct ocean views-1230

Other vacation rentals with a pool

5 out of 5 average rating, 5 reviews

A balcony offers a serene view of the ocean at sunset, showcasing striking colors in the sky. Comfortable seating is provided with two lounge chairs and a small table, creating a space for relaxation while enjoying the scenery.

Apartment in Perdido Key

Beachfront Paradise Perdido Key

4.93 out of 5 average rating, 76 reviews

Pickleball Paradise w/Private Hot Tub, Pool & Bar

A serene backyard features a refreshing pool surrounded by lush greenery. Comfortable lounge chairs are positioned under an umbrella, while potted plants add a touch of nature. A patterned outdoor rug connects the seating area to the pool, creating an inviting space for relaxation.

4.88 out of 5 average rating, 97 reviews

Pool House at Indigo Cove, Close to NAS!

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

5 out of 5 average rating, 46 reviews

A well-maintained outdoor area features a swimming pool surrounded by a spacious patio, equipped with several lounge chairs and a shaded seating area. Lush greenery frames the space, with a tall umbrella offering additional shade. A grill is positioned nearby for outdoor cooking.

Home in Northpointe

Pensacola Pistachio Pool Paradise

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

An aerial view captures the Sabine Yacht and Raquet Club, a multi-story building situated near the sandy beach. The Gulf of Mexico's blue waters stretch out beyond the shore. Surrounding areas include a tennis court, a swimming pool, and a boat dock along the coastline.

4.89 out of 5 average rating, 76 reviews

Beautiful Gulf View Waterfront Condo

Superhost

An expansive terrace is shown, featuring a round dining table surrounded by black metal chairs. Scenic views of the Gulf of Mexico and sandy beach extend into the horizon under a clear blue sky.