
Holiday rentals with a pool in Pensacola Beach
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Pensacola Beach

Total holiday rentals
Explore 2,230 holiday rentals in Pensacola Beach

Nightly prices starting at
Pensacola Beach holiday rentals start at $137 NZD per night before taxes and fees

Verified guest reviews
Over 49,350 verified reviews to help you choose

Family-friendly holiday rentals
2,010 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 210 rentals that welcome pets

Rentals with dedicated workspaces
1,210 properties have a dedicated workspace

Wi-Fi availability
2,200 of Pensacola Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pensacola Beach rentals

4.8 Average rating
Pensacola Beach stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Pensacola Beach
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

Serenita Ora: Quiet Waterfront Unit with 2 Kayaks!
Welcome to Serenita Ora! Come enjoy beautiful views, coffee on the balconies and the peaceful waters. Our oasis sits directly on a calm, shallow cove of Perdido Bay, providing the perfect place for families to play safely. *BOAT SLIP AVAILABLE TO RENT* This 2 bed/2.5 bath sleeps 5-6 and includes a full kitchen, laundry, and 2 Kayaks! Spend all day right here enjoying the quiet serenity, tucked away from the hustle and bustle. Or take a short 5 minute drive to Perdido Key Beach, restaurants, etc.

East Bay Hideaway — A Private Waterfront Escape
Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

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.

Waterfront, sleeps 7, walk to everything!
Recently updated 2 bedroom, 2 bathroom 1200 sq ft. large open concept living and dining space and washer/dryer in the unit. Double sliders to the triple size balcony with amazing sunset views over The Little Sabine Bay and The Gulf of Mexico. Centrally located across the street from Casino Beach, The boardwalk, and great restaurants. This is truly one of the best spots on the island with the best of everything including the most amazing views with the convenience of walkability to everything.

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.

$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!

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!

Best view on the beach! Beach gear included!
Beautiful 1 bedroom, 1.5 bath condo sleeps 6. Bring your swimsuits and get ready to relax! Condo is on 12th floor, tower closest to the pier. - 1 bedroom with king size bed, cozy bunk area for kids, and gel foam mattress on fold-out sofa. (ALL MATRESSES NEW IN SEPTEMBER 2025). - All linens and towels provided, including beach towels! - 2 beach chairs, 2 boogie boards and a beach umbrella included - Washer & dryer - Fully equipped kitchen to enjoy dinner with a view - Wi-Fi & cable

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p
Welcome to The Diving Dolphin... a 2 bedroom/ 2 bathroom condo located in Emerald Isle Condominium complex~ Directly on Pensacola Beach! This beautiful condo is located on the 5th floor and overlooks the stunning waters of the Gulf of Mexico! Come on in and relax- this condo has it all! The condo has a capacity to comfortably sleep 6. We will send you a welcome packet with details about the complex, unit and area! ~COMPLIMENTARY BEACH CHAIR & UMBRELLA SET UP MARCH - OCTOBER!~

Beachfront Condo • Pool & Resort Perks
Welcome to Pensacola Perch, an 8th‑floor beachfront condo offering expansive views of Pensacola Beach—perfect for dolphin watching and catching the Blue Angels airshow. This modern 2BR/2BA condo sits in the highly sought‑after Emerald Isle gated resort, where guests enjoy premium amenities including direct beach access, two swimming pools, a hot tub, sauna, and a beachfront fitness center. From March–October, enjoy complimentary beach chairs and an umbrella from La Dolce Vita.

Soundside Paradise
Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!
Popular amenities for Pensacola Beach rentals with a pool
House rentals with a pool

Hot tub/ Pool Relaxing Getaway

Beautiful Paradise Home - 1 Mile From Beach - POOL

Poolside Family Retreat w/ Hot Tub & Game Room

Private Pool-Near NAS-Grills-Game Room FamilySetUp

Historic Downtown Bayfront Home Pool Mins to Beach

Casa Verde: Heated Pool +JET SKI & Pontoon rental

Condo on Pensacola Beach

Quiet Pool Home Getaway! Airbnb's FAV Home! TOP 1%
Condo rentals with a pool

Melody of the Sea - On the Beach - Incredible View

Welcome To Florida's Hidden Gem!

Stay at Sunshine Daydream on Pensacola Beach

2B Gulf Views at Emerald Dolphin 540 - Pet

Bayside Retreat-Panoramic Sunset Views

Welcome to Pura Vida: Top-Floor View & Beach Bliss

Pensacola Beach Condo w/ Great Views (F12)

Bluewater 306 Direct Gulf Front, HUGE Wrap Balcony
Other holiday rentals with a pool

King Bed Paradise | Outdoor Theatre | Paddleboards

Fabulous 2 bedroom end unit at South Harbour - 4A

Private Saltwater Pool Home Near Pensacola Beach

Pensacola Beach Bungalow Heated Pool & Golf Cart

The Intendencia Country Club

Gulf Front w/Terrace in Tower 3!

Sunset Social @ The Boardwalk Condo

Beach Club 1906 - 𝑷𝒂𝒓𝒂𝒅𝒊𝒔𝒆 𝑭𝒐𝒖𝒏𝒅
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- Destin Beach
- Gulf Shores Public Beach
- Crab Island
- Destin Harbor Boardwalk
- Perdido Key Beach
- OWA Parks & Resort
- Opal Beach
- Henderson Beach State Park
- Village of Baytowne Wharf
- Gulf State Park
- Navarre Beach Fishing Pier
- Flora-Bama Lounge
- Johnson's Beach, Gulf Islands National Seashore
- Alabama Point Beach
- The Hangout
- HarborWalk Village
- Gulf Breeze Zoo
- The Wharf Amphitheater
- The Lighthouse Condominiums
- Fort Walton Beach Landing
- Jade East Towers
- The Boardwalk on Okaloosa Island
- Gulfarium Marine Adventure Park
- Destiny East





