
Vacation rentals with a pool in Pensacola
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pensacola
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

East Bay Getaway - Studio with Pool & Hot Tub
Welcome to East Bay Getaway, a private studio nestled in the woods. This clean and comfortable room with private entrance is a MIL suite attached to your host's home, on more than an acre. It features a kitchenette (no stove), high-speed WiFi, 32" smart TV, and dedicated HVAC system. Plenty of outdoor space, with a large pool and hot tub in the shared, privacy fenced backyard. A bike/walk path is directly across the street, which goes for miles either direction. 3- burner BBQ grill - NEW for 25!

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.

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!

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.

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.

Backyard Oasis Family friendly Pensacola Beach, FL
Welcome to Paradise w/ POOL. Kid friendly. Now that we have rented out our home there are two main things to note: 1) we live upstairs and you will hear our kids footsteps. (7-8am). No complaints about voices. 2) our pool is Not heated. Enjoy sound side beach access RIGHT across the street! Best sunsets on the beach! Gulf of Mexico is 5 blocks away. Private lanai with grill and pool access. Enter underneath the stairwell into your unique private 2 bedroom 1 bath suite. Keypad on door.

Sunset on the Bayou near NAS/Downtown Pensacola
If you’re looking for a quiet get-away on the water, you will find it here. Our cozy 2 bed/2 bath condo is like a cottage by the sea in a condo setting. Relaxing coastal decor and a beautiful view from the balcony make our home enjoyable inside and out. Enjoy all the amenities of home, sunbathe by the pool, fish from the dock, relax on the balcony, grill out on the lawn. Its all here. Just a short drive from Pensacola NAS, Pensacola Beach and historic Downtown Pensacola. (No pets allowed)

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!

Poolside Family Retreat w/ Hot Tub & Game Room
PLEASE READ entire description to ensure accurate expectations. Relax while the kids play! Enjoy a private pool (seasonally heated), bubbling hot tub, and A/C game room packed with fun. Parents can unwind in the new massage chair or simply enjoy the peaceful backyard oasis. Centrally located—just 10 min to Downtown, 20 to Perdido Key, and 30 to Pensacola Beach—this family retreat blends relaxation, comfort, and connection for your perfect getaway!

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!

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.

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
House rentals with a pool

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

The Palm Oasis | Heated Pool • Hot Tub • Beach

5BR*Heated Pool*Fire Pit*Pet Friendly*Fenced Yard

Cozy Ranch House/Screened in Pool/ 3BD

Private Pool-Near NAS-Grills-Game Room FamilySetUp

Pensacola Serenity Hot tub mini Golf arcade games

The Carriage House: relaxing stay with pool

Saltwater Pool! Cottage-Mins to Downtown & Beaches
Condo rentals with a pool

Marisol del Cielo/Sea Sun Of The Sky-On The Beach

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

Beachfront Bliss: Walk to Dine & Play on Sands

Walk to Everything-Best Sunset-Comfy King-Stocked

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p

Pensacola Beach Condo w/ Great Views (F12)

This is the one! Perfect Getaway near the beach.

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

Beautiful Pensacola Beach Home

Private-Relaxing, Pool, Dwntwn PNS & Beaches

Cozy Coastal Downtown Home

*Vitamin Sea* (Ocean View, w/ Beach Supplies)

Tranquil and Spacious Condo - PBC 110

Elegant townhome + oversized luxury pool

Pensacola Downtown Poolside Paradise w/ King Bed

3BR/2BA home by Gulf Islands National Seashore
When is the best time to visit Pensacola?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 CAD | $183 CAD | $220 CAD | $205 CAD | $220 CAD | $247 CAD | $272 CAD | $224 CAD | $199 CAD | $188 CAD | $187 CAD | $172 CAD |
| 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 vacation rentals with a pool in Pensacola

Total vacation rentals
Explore 130 vacation rentals in Pensacola

Nightly prices starting at
Pensacola vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 8,920 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Pensacola vacation rentals include wifi access

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

4.8 Average rating
Pensacola stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Pensacola’s top spots, include Palafox Market, Pensacola Museum of Art, and Bruce Beach
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