Holiday rentals with a pool in Pensacola

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, 126 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, 216 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.

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 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, 213 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of Mexico from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach! Nothing separates you from the best white-sand beach on the Gulf Coast. This beach condo boasts a vibrant interior filled with beach-themed accents, a private balcony with sweeping ocean views, and access to 2 pools (1 heated) and a hot tub. Enjoy the best restaurants and shopping on the beach, all within a short walk.

5 out of 5 average rating, 123 reviews

Quiet & Cozy Family Home! Perfect Winter Stay!

Welcome to your quiet Pensacola getaway! The perfect home base for beach days, Blue Angels excitement, and relaxing evenings. Located in a peaceful neighborhood just minutes from Pensacola Beach, NAS Pensacola, and downtown, this clean and comfortable home is ideal for families, couples, military visitors, and longer winter stays. Whether you’re here for the sugar-white beaches, aviation events, or a laid-back escape, this home offers space, convenience, and comfort without the crowds.

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.

4.97 out of 5 average rating, 174 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.

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.

4.97 out of 5 average rating, 132 reviews

Poolside Retreat, Hot Tub, 5 min to beach

Looking for the perfect place to stay for your beach vacation? Look no further! Our beautiful, newly furnished home has everything you need for the perfect vacation including your own private pool and hot tub!!! The pool is in a screened in enclosure (bye bye bugs) and surrounded by a covered patio with comfy seating, a sit up bar w/beverage fridge, outdoor TV and a dining table for six. Or kick back and relax poolside in our hammock.

4.89 out of 5 average rating, 122 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

This two story home in Redfish Harbor provides a beach getaway in Perdido Key, Florida. Enjoy the many neighborhood amenities including a dock onto Bayou Garcon, a pool, pickle ball courts and a bocci ball court. This place is perfect for family vacations, a couples getaway or just some fun in the sun with friends. Let the spacious luxury of this home lull you into relaxation.

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.

4.93 out of 5 average rating, 106 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

Wi-Fi

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

4.93 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.

4.93 out of 5 average rating, 74 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.

4.87 out of 5 average rating, 94 reviews

Pool House at Indigo Cove, Close to NAS!

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.

Home in Pensacola Beach

4.8 out of 5 average rating, 81 reviews

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

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 outdoor area features a hot tub alongside a round stock tank pool, each inviting relaxation. A colorful beach ball floats in the stock tank pool. A lounge chair is placed next to the hot tub, surrounded by green grass and gravel.

4.94 out of 5 average rating, 65 reviews

Amazing Hot Tub/ Stock Tank Pool

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

Condo rentals with a pool

4.95 out of 5 average rating, 155 reviews

A spacious balcony dining area is shown, furnished with a wooden table set for six. The ocean and beach are visible in the background, alongside a large pool area with lounge chairs. The clear blue sky complements the tranquil seaside view.

Condo in Perdido Key

Palacio 203 BeachFront Best View 2 Pools Hot Tub!

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 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

4.79 out of 5 average rating, 214 reviews

A panoramic view of the Gulf of Mexico stretches across the horizon, showcasing clear blue waters meeting a sandy shoreline. Sunlight glistens on the water, creating a serene atmosphere. A few figures can be seen enjoying the beach, enhancing the tranquil coastal scene.

Condo in Navarre Beach

Welcome To Florida's Hidden Gem!

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 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

4.95 out of 5 average rating, 168 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

4.91 out of 5 average rating, 105 reviews

A living area is displayed, featuring a comfortable gray sofa with decorative yellow pillows. A set of nested coffee tables sits in front, with a simplistic design. A wall-mounted television and a decorative fireplace are visible, while natural light filters through a window adorned with light curtains.

Condo in Pensacola

Stylish 1 bdrm condo. May sleep 4. Just off I10

Other holiday rentals with a pool

A sunlit living room features a full-size sofa and two accent chairs, complemented by a large Smart TV mounted on the wall. Sliding glass doors open to a balcony offering bay views, with natural light filtering through the beige curtains.

5 out of 5 average rating, 41 reviews

Baywatch Retreat 2/2 Beach Condo w/Pool

4.97 out of 5 average rating, 34 reviews

2BR Condo in Pensacola Beach

4.97 out of 5 average rating, 63 reviews

A wooden deck is featured at the front of a small cabin, outlined by a sturdy railing. Comfortable seating is seen on the deck, shaded by a canopy. A circular firepit made of stone is located on the ground nearby, surrounded by gravel.

Guesthouse in Pensacola

The Rosales serenity suite

5 out of 5 average rating, 14 reviews

Home in Gulf Breeze

Gulf Breeze Oasis-Pool, Hot tub, BBQ, nearby beach

Guesthouse in Pensacola Beach

5 out of 5 average rating, 10 reviews

Gulf Breeze Bungalow

4.93 out of 5 average rating, 76 reviews

An outdoor patio is shown, featuring a fire pit surrounded by comfortable seating. A swimming pool is visible in the background, with lush greenery framing the area. The evening sky creates a serene ambiance, complemented by the flickering flames from the fire pit.

Guest suite in Pensacola

Private Suite with Saltwater pool

4.86 out of 5 average rating, 28 reviews

The living area showcases comfortable seating arrangements with a large, gray sectional sofa and a patterned chair. Natural light floods through floor-to-ceiling sliding glass doors, leading to an expansive balcony with ocean views. A neutral color palette complements coastal decor.

Condo in Perdido Key

Beach Colony East Penthouse 15C

A screened-in swimming pool area features clear blue water, with lounge chairs positioned nearby. Sunlight reflects off the water's surface, and a grassy lawn surrounds the pool area. The house is visible in the background, providing additional context to the outdoor space.