
Holiday rentals with a pool in Pensacola Beach
Find and book unique homes with a pool on Airbnb
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.

Ocean Tranquility label by guest“Heaven on Earth”.
Relax with the family at this restful retreat “Heaven on Earth” as one reviewer described. This is our home away from home and is owner managed. Owner management. We offer more personal touches. (hand picked towels bedding and a coffee bar), but more importantly is our exceptional housekeeper. She has over 20 years of experience and over 100 5 star reviews for cleanliness. Memorial Day thru Labor Day we offer free umbrella and two beach chairs. The booker must list names of guests & ages.

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.

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.

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.

Stay at Sunshine Daydream on Pensacola Beach
Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Newly renovated condo with amazing water views!
Experience the clear blue water and white sand of Pensacola Beach. Enjoy spectacular views of Pensacola Bay from a private 3rd floor balcony. This newly renovated condo offers solid surface floors throughout, a fully stocked kitchen and calming beach decor. The master has a queen size bed, flat screen TV, and ensuite bathroom. The 2nd bedroom offers 2 full size bunk beds. The main living room has another flat screen TV, comfortable couch and is a perfect place for your group to gather.

Phoenix X 1105- 1BR Florabama Beach Luxury Suite
NOTICE- CONSTRUCTION: APRIL 20th, 2026. Expansion Joint Sealing Project Starts. This meticulously maintained and beautifully furnished Phoenix 10 condo is the epitome of elegance and sophisticated luxury for the discerning couple or small family seeking respite in a beach resort setting. Situated directly on the beach! Parking available from HOA for $70 fee. Linens, towels and complementary starter package (TP/ paper towels, dish detergent and shampoo provided). Min age to book 25

Pelican's Perch @ Villas on the Gulf
This renovated 2 bed/1.5 bathroom condo is stocked and ready to go--Just bring your groceries and swimsuits! This quaint little beach condo is the perfect, affordable getaway you are looking for. In less than a two-minute walk from the front door, you can have your toes in the sand, soaking up the sun on the Gulf. It features a carport for private parking, two bedrooms, w/ a King bed in one room, two full beds in the other, a couch in the living area, and a queen air mattress.

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.

Wake to Gulf Views, Heated Pool Getaway
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.

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

Beautiful Paradise Home - 1 Mile From Beach - POOL

The Sunshine House | Private Pool + Gulf Views

Poolside Family Retreat w/ Hot Tub & Game Room

East Bay Hideaway — A Private Waterfront Escape

Private Pool-Near NAS-Grills-Game Room FamilySetUp

Pensacola Blue Angel Pool House

Del Sol-Outdoor Oasis with Pool and Hot Tub

Private Pool / Two living rooms /Downtown
Apartment rentals with a pool

Beach Colony East Penthouse 16B

Welcome to "Fanta Sea" @ Waterscape Resort~A328~

Palm Beach Oasis - Waterfront and Quiet

Beachfront ☀️ Waterfront 🌊 180 ° views in 🧡 of OB

Gulf Getaway+ Waterfront Views *Fully Updated*

2BR Condo in Pensacola Beach

Tranquil and Spacious Condo - PBC 110

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p
Other holiday rentals with a pool

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

Open Concept Coastal 5 Bed Heated* Pool/ Game Room

Rainbow Land Carriage House

Portofino Tower 1 - 9th-Floor Knockout

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

Cozy Ranch House/Screened in Pool/ 3BD

Turtle Spa House III

~*Casa Florado |Private Beach Club|Bar|Pool*~
When is the best time to visit Pensacola Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $242 SGD | $241 SGD | $296 SGD | $273 SGD | $340 SGD | $431 SGD | $478 SGD | $327 SGD | $273 SGD | $276 SGD | $252 SGD | $248 SGD |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°C |
Quick stats about holiday rentals with a pool in Pensacola Beach

Total holiday rentals
Explore 2,210 holiday rentals in Pensacola Beach

Nightly prices starting at
Pensacola Beach holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 45,510 verified reviews to help you choose

Family-friendly holiday rentals
1,950 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Rentals with dedicated workspaces
1,150 properties have a dedicated workspace

Wifi availability
2,180 of Pensacola Beach holiday rentals include wifi 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!
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- Gulf State Park
- Destin Beach
- Gulf Shores Public Beach
- Perdido Key Beach
- Crab Island
- Destin Harbor Boardwalk
- Pensacola Beach
- Alabama Point Beach
- OWA Parks & Resort
- Opal Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Village of Baytowne Wharf
- Flora-Bama Lounge
- Gulf Breeze Zoo
- The Hangout
- Henderson Beach State Park
- HarborWalk Village
- Waterville USA/Escape House
- Adventure Island
- Gulfarium Marine Adventure Park
- The Boardwalk on Okaloosa Island
- The Track - Destin
- Fort Walton Beach Landing





