Holiday rentals with a pool in 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, 224 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of America from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach, named America’s Best Beach by the Condé Nast Traveler Readers’ Choice Awards! 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.

4.99 out of 5 average rating, 130 reviews

Private Pool-Near NAS-Grills-Game Room FamilySetUp

You have found a home that is loved by so many who come to Pensacola! This home offers so much for families: arcade room, 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 events as kite fest, wahoo games, bands on the beach, theater, Friday art nights and parades! BookNow

4.99 out of 5 average rating, 177 reviews

A bright living area features a spacious white sectional sofa adjacent to a light wood coffee table. Floor-to-ceiling glass doors offer expansive views of the ocean and sky, enhancing the openness of the space. A dining set is visible on the balcony.

Apartment in Perdido Key

Melody of the Sea - On the Beach - Incredible View

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! Beautifully remodeled and updated! This retreat has the rare double windows to enjoy stunning panoramic sunset views! On the beach (No roads to cross)! Resort has indoor heated pool & outdoor pool & hot tub overlooking the ocean. 2 fireplaces in the living room bedroom for those cozy mild winters. King size bed in the master... nautical bunkbeds with port holes & queen sleeper sofa in the main living areas. Reserve Your Time Away Today

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.

4.9 out of 5 average rating, 220 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, 108 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!

5 out of 5 average rating, 132 reviews

Pensacola Gem! Airbnb's Favorite Home! TOP 5%!

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, quick visits or longer 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.

A spacious single-story home features a blend of stone and siding, surrounded by a manicured lawn. The entrance is marked by a wide porch, complemented by large windows and shutters on either side. A driveway leads toward the garage on the left.

4.85 out of 5 average rating, 109 reviews

Pensacola Blue Angel Pool House

Plenty of Space! Wonderful quiet home with a heated pool in a gated community on the outskirts of town. Located 20-25 min from Perdido Key and Pensacola beaches. The home is excellent for large groups or gatherings. The master bedroom is on one side of the house with all other bedrooms on the opposite side. The master bathroom has a garden tub for relaxing and a huge walk in closet. Outdoor patio is screened patio has an indoor firepit and plenty of games. We look forward to hosting you!

4.88 out of 5 average rating, 104 reviews

A spacious living room is furnished with a large sectional sofa and a matching ottoman, set atop a decorative area rug. Natural light is provided by windows, with ceiling fans enhancing the comfortable atmosphere.

Home in Sanders Beach

Private Pool / Two living rooms /Downtown

This 3000sqft home features a private pool, two living rooms, four bedrooms, two bathrooms, a kitchen, and a beautiful sunroom overlooking a private pool! Two families traveling together?? This is the ideal home for you! This home sleeps 10 comfortably but can accommodate more with the use of an air mattress or crib if traveling with a toddler. Located just a few blocks from Joe Patti's, the Blue Wahoo Stadium, and Palafox Street! YOU AGREE TO ALL HOUSE RULES WHEN YOU BOOK. READ THEM.

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.

4.98 out of 5 average rating, 118 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.

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.

4.96 out of 5 average rating, 148 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.

4.99 out of 5 average rating, 166 reviews

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.

Apartment in Perdido Key

Beach Front, Low Density Condo in Perdido Key!

DON'T FIGHT THE CROWDS for space on the beach! Unwind in our comfortable 4th floor Beach Front "Slice of Paradise" with private beach. The balcony offers unobstructed, gorgeous views of the Gulf and the beautiful white sands of Perdido Key. Soak up the sun as you kick back on the balcony and count the dolphins while being lulled by the sound of the waves and the salt air breeze.

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, 122 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

4.96 out of 5 average rating, 56 reviews

The outdoor space features a heated pool, accompanied by three illuminated spheres on the water's surface. Comfortable loungers and a dining table with chairs are positioned around the area, while an umbrella offers shade. A wall-mounted TV is visible under the covered patio.

Home in Sanders Beach

Luxury Heated Pool Home 8Beds 2.5BA 15min To Beach

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, 109 reviews

Hot tub/ Pool Relaxing Getaway

5 out of 5 average rating, 18 reviews

Home in Navarre

The Palm Oasis | Heated Pool • Hot Tub • Beach

A serene swimming pool is enclosed within a screened structure, capturing the reflection of a colorful sunset on its surface. Lush green fields are visible in the background, providing a tranquil view beyond the pool area.

4.88 out of 5 average rating, 24 reviews

Cozy Ranch House/Screened in Pool/ 3BD

5 out of 5 average rating, 8 reviews

Home in Navarre

The Witch & Pirate | Pool | Pub | BBQ | Unwind!

Superhost

A luxurious spa master bath is featured, showcasing a freestanding white tub set against elegant marble walls. Natural light illuminates the space, highlighting the modern black faucet and sleek design elements of the bathroom.

4.88 out of 5 average rating, 81 reviews

Pensacola Serenity Hot tub mini Golf arcade games

5 out of 5 average rating, 42 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

4.88 out of 5 average rating, 32 reviews

The exterior of the home is captured from above, showcasing a manicured lawn surrounded by trees displaying various autumn colors. Notable features include a curved driveway leading to a front entryway and palm trees flanking the entrance, emphasizing a welcoming atmosphere.

Home in Gulf Breeze

Kelsey's Cove

Apartment rentals with a pool

A balcony space features a hanging chair and a small side table, surrounded by decorative lattice railing. The sun sets in the background, casting a warm glow over the calm water and buildings lining the shore.

5 out of 5 average rating, 37 reviews

Sea-Sun's Greetings • Pensacola Beach • 2BR Condo

Apartment in Orange Beach

4.99 out of 5 average rating, 154 reviews

Beachfront ☀️ Waterfront 🌊 180 ° views in 🧡 of OB

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, 103 reviews

Pensacola Beach, Florida 1BR Amazing View

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.

4.96 out of 5 average rating, 226 reviews

$0 clean fee! Beachside/pool view/king bed/jacuzzi

4.96 out of 5 average rating, 224 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.

Apartment in Perdido Key

This is the one! Perfect Getaway near the beach.

A light-filled living space features a comfortable couch adorned with soft cushions. A coffee table rests on a textured area rug, complemented by a small plant. The adjacent dining area and kitchen can be seen in the background, adding to the open and inviting layout.

4.95 out of 5 average rating, 169 reviews

Pelican's Perch @ Villas on the Gulf

Apartment in Navarre Beach

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, 181 reviews

La Playa Esmeralda - Panoramic Sunset Views

4.91 out of 5 average rating, 110 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.

Apartment in Pensacola

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

Other holiday rentals with a pool

Superhost

A private fenced pool is surrounded by a spacious patio area, featuring comfortable lounge chairs. Lush greenery is visible in the background, with a well-maintained yard offering ample space. Sunlight reflects off the clear water, creating a serene atmosphere for relaxation.

Home in Scenic Heights

4.89 out of 5 average rating, 9 reviews

Beautiful Pensacola Beach Home

A decorative knight statue stands beside a window, holding a shield marked with 'Round Table Resort'. Its silver armor is detailed with engravings, and the knight's visor partially covers its face. Green plants are placed near the base, enhancing the welcoming exterior.

5 out of 5 average rating, 62 reviews

Open Concept Coastal 5 Bed Heated* Pool/ Game Room

4.93 out of 5 average rating, 14 reviews

A modern three-story home is situated among lush greenery, visible under a vibrant sunset sky. Multiple balconies offer opportunities for outdoor enjoyment, while a driveway leads to a two-car garage. Palm trees and landscaped areas enhance the home’s welcoming appearance.

Home in Perdido Key

Walk/Bike/Golf Cart to Beach | Luxury Home w/Pool

5 out of 5 average rating, 25 reviews

A well-constructed carriage house features a spacious front porch with black railings and rocking chairs. The overhang creates a shaded area, while the driveway leads to the garage beneath. Lush trees surround the house, complementing the gravel pathway and landscaped areas.

Guest house in Milton

Rainbow Land Carriage House

5 out of 5 average rating, 19 reviews

Home in Gulf Breeze

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

4.97 out of 5 average rating, 30 reviews

Cozy Coastal Downtown Home

4.95 out of 5 average rating, 78 reviews

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A coffee table sits in front, accompanied by small potted plants. Natural light filters in through large windows, while a dining area and a kitchen bar with stools are visible in the background.

Townhouse in Pensacola

Elegant townhome + oversized luxury pool

An inviting above ground pool is surrounded by a wooden deck, featuring a circular shape and clear blue water. Comfortable lounge chairs are positioned nearby, offering a relaxing spot to enjoy the sun. Tall trees and a privacy screen add a sense of seclusion to the area.