House holiday rentals in Pensacola

The living area features a light-colored sofa and two armchairs, complemented by decorative pillows. A coffee table is centrally placed, with a woven tray on top. Soft lighting is provided by multiple lamps, and large windows are adorned with sheer curtains, allowing natural light to enter.

4.96 out of 5 average rating, 117 reviews

Midtown Luxury Stay w/Courtyard

Centrally located in Pensacola's thriving shopping district, your home base 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!

A charming cottage is set within a lush yard, featuring a welcoming front porch adorned with potted plants. A brick pathway leads to the entrance, framed by vibrant greenery and shaded by mature trees in the background.

4.96 out of 5 average rating, 171 reviews

Walk To Downtown, Fenced Yard, Games, Fire Pit

Welcome to Cooper's Cottage a beautifully renovated 1933 home in the Garden District of Pensacola less than one mile from downtowns historic Seville Square and Palafox St. where you will enjoy bars, restaurants , shopping, art galleries and more. Just 15 min to Pensacola beach and close to NAS home of the Blue Angels. Relax in our fully fenced, pet friendly back yard with gas grill, outdoor dining, lounge seating with fire pit. There are 2 bikes, outdoor games and more. Smart TVs in each room

4.92 out of 5 average rating, 115 reviews

Comfortable Downtown Stay • Pet Friendly Yard

Charming, pet-friendly cottage in Downtown Pensacola! Just minutes to beautiful beaches, Palafox Market, breweries, coffee shops, and the Blue Angels. Enjoy a spacious fenced yard for your pups, fast, reliable Wi-Fi, and a game room for fun nights in. Perfectly stocked for military families, wedding guests, staycations, or remote work. Close to parks, shopping, and dining. Dogs welcome—with treats and bowls! Feel right at home in this comfortable, convenient, and well-located Pensacola escape.

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, 214 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.

4.99 out of 5 average rating, 140 reviews

Modern, cozy, pet-friendly cottage w/king

Auer House (pronounced “our”) is a spacious, modern downtown Pensacola home steps from walkable restaurants and parks. Experience NAS Pensacola and the Blue Angels…sit on the front porch and hear their roar as you catch a glimpse as they practice! We are near the Blue Wahoos Stadium, Joe Patti’s and all the festivals! And Fido is welcome; there’s a dog park across the street! Unwind in this super clean retreat featuring fast WiFi, or sit outside around the fire pit, disconnect and reconnect!

A spacious backyard is illuminated by soft lights, featuring a central gravel area. Woven hammocks are positioned for relaxation, surrounded by a grassy lawn and a wooden fence that provides privacy. Trees stand tall, contributing to the inviting outdoor atmosphere.

4.99 out of 5 average rating, 181 reviews

The Hosta Hangout - A Luxury Central Haven!

Welcome to the Hosta Hangout! This modern duplex embraces a bohemian feel which creates a welcoming space of relaxation and bright engagement. Slow down and decompress in a woven hammock. Laugh with friends and family as you gather around the warm fire or relish the moments of a family cookout. However you choose to spend your time, embrace the uniqueness of this space that had the experience in mind. There are 2 cameras on the exterior of the property which actively record audio & visual.

4.87 out of 5 average rating, 163 reviews

Home in Perdido Key

Blue Heaven: Wonderful Waterfront Unit with Kayaks

Welcome to Blue Heaven! This lovely waterfront home sits on a calm, shallow cove of Perdido Bay, providing GORGEOUS views & the perfect place for families to relax, swim & paddle safely, all directly behind the house. This 2 bed/2.5 bath sleeps up to 6 & includes a full kitchen, laundry, 2 kayaks, a paddle board & more! Spend all day enjoying the onsite beach, heated community pool, kayaking, swimming or take a quick drive to Perdido Key Beaches, dining, and more! Continue for more Details

A charming cottage exterior is presented, featuring a welcoming front porch with two chairs. A stone pathway leads to the entrance, surrounded by a landscaped yard with greenery. The building is framed by trees, creating a serene atmosphere during twilight.

4.95 out of 5 average rating, 198 reviews

The Gray Lady - A Beautiful Cottage in Pensacola!

The Gray Lady is a luxurious cottage in downtown Pensacola. It combines two pieces of paradise - named after Nantucket and located in Pensacola. This home sleeps 9. Relax in the backyard oasis, equipped with a private hot tub! A park, brewery, and restaurants are all within walking distance. Just a mile from downtown, be sure to checkout the restaurants, shops, and nightlife! Pensacola Beach, NAS, Fort Pickens, the mall and airport are all 15 mins away. We hope you enjoy your stay!!

4.96 out of 5 average rating, 205 reviews

The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.

Home in Milton

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

4.94 out of 5 average rating, 358 reviews

An exterior view of the property features a vibrant orange and blue facade. A winding stone path leads to the entrance, surrounded by lush green grass. A patio area is set with outdoor furniture and an umbrella, while colorful kayaks rest against the side of the building.

Home in East Hill

The Orange Bayview 🍊 Pet Friendly 🐬Studio Suite 🌴

Orange You Glad You Found This Place? Steps from Bayview Park including small and large dog parks, dog beach, tennis courts, workout area, boat ramp, Bayview Center & more. 5 minutes to downtown, 15 minutes to Pensacola Beach. While attached to the main house, the guest suite is its own private space, with a separate entrance, temperature control, driveway parking for 2 and room for a 20’ boat. We’ll do anything to make your stay great!

4.99 out of 5 average rating, 124 reviews

The RED DOOR: Explore Downtown Pensacola & Venues!

Step into history at The Hawkins House — a meticulously preserved 1880s gem in downtown Pensacola. This 2,000-sq-ft retreat blends vintage charm with modern comfort, offering a Southern ambiance on a peaceful side street. Sunlit and elegantly furnished, it highlights authentic 19th-century details. Sleeps six comfortably and welcomes screened pets (fee). Your perfect downtown getaway awaits!

4.91 out of 5 average rating, 117 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.

Popular amenities for Pensacola house rentals

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.

4.92 out of 5 average rating, 106 reviews

Hot tub/ Pool at this Relaxing Getaway

4.93 out of 5 average rating, 108 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.

4.97 out of 5 average rating, 173 reviews

A wooden dock extends into calm waters, flanked by two covered structures in the distance. The scene is under a bright blue sky, adorned with fluffy white clouds, creating a serene atmosphere for fishing or relaxation.

Home in Navarre

East Bay Hideaway - Sun. Swim. Sunset. Stargaze.

4.99 out of 5 average rating, 126 reviews

Private Pool-Near NAS- Grills-Arcades-FamilySetUp

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, 103 reviews

Pensacola Blue Angel Pool House

4.98 out of 5 average rating, 54 reviews

A spacious backyard is showcased, featuring a crystal-clear pool surrounded by a stone patio. Lounge chairs are arranged near the water, and a shaded seating area is present nearby. Lush greenery adds privacy, and a wood fence frames the perimeter of the yard.

Home in East Hill

5 BR house with heated pool*

Home in East Pensacola Heights

A heated saltwater pool is showcased in a private outdoor space, surrounded by a wooden privacy fence. The pool is framed by paved stones, with a comfortable seating area partially visible in the background, creating an inviting setting for relaxation.

4.81 out of 5 average rating, 145 reviews

Saltwater Pool! Cottage-Mins to Downtown & Beaches

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, 124 reviews

Poolside Retreat, Hot Tub, 5 min to beach

Weekly house rentals

4.89 out of 5 average rating, 72 reviews

A spacious bedroom features vibrant green walls and a large, neutral-colored quilted bedspread. Two wooden nightstands with lamps are positioned on either side of the bed, accented by decorative pillows in shades of coral. Natural light fills the room from a nearby window.

Home in Old East Hill

Gadsden Hideaway: Historic Downtown Luxury in East

A charming front porch is featured, with two floral-patterned chairs positioned around a small table. A blue door offers a welcoming entrance, and a landscaped area with greenery complements the light-colored siding. A pathway leads to the porch, enhancing accessibility.

4.94 out of 5 average rating, 80 reviews

Piece of Paradise

4.98 out of 5 average rating, 43 reviews

The living area features a cozy blue sofa adorned with patterned pillows, facing a rustic brick fireplace. A sleek staircase with a metal railing leads to the upper level. A wooden coffee table rests in front, displaying decorative items, while natural light filters through nearby windows.

Home in Old East Hill

The Blue House on Belmont!

A modern living area is highlighted by white armchairs and a wooden coffee table. A round dining table is set against a wall adorned with circular decor. The space features light wooden cabinetry and an island in the kitchen area, with natural light streaming through the windows.

4.97 out of 5 average rating, 31 reviews

Downtown Historic Cottage

4.99 out of 5 average rating, 83 reviews

Home in East Hill

Simply Unwind: a retreat style stay. EV Charger

A compact kitchen features light gray cabinetry and a marble countertop. Stainless steel appliances, including a refrigerator and an oven, are visible. Shelves hold dishware and glassware, while a large clock adorns the wall. A rug adds warmth to the tiled floor.

4.75 out of 5 average rating, 189 reviews

1-Bedroom Cottage, Single-Family

A illuminated neon sign reading 'After Dark Playground' is displayed against a textured wall. The warm glow of the sign is complemented by soft orange lighting above, creating an inviting and intriguing atmosphere.

5 out of 5 average rating, 45 reviews

After Dark Playground

A serene bedroom features a spacious blue upholstered bed positioned against a light-colored wall. Natural light streams in through two windows with horizontal blinds, illuminating the room's neutral decor. A ceiling fan offers a modern touch, while a glimpse of a doorway is visible in the background.

4.81 out of 5 average rating, 78 reviews

Urban Escape on D St

Private house rentals

4.93 out of 5 average rating, 73 reviews

Pickleball Paradise w/Private Hot Tub, Pool & Bar

A bright and modern kitchen area features a spacious counter with two stools, a stainless steel refrigerator, and a microwave. A cozy sofa is positioned in the living area, accompanied by a stylish armchair. Natural light enters through the window, highlighting the wood flooring.

4.93 out of 5 average rating, 60 reviews

Tiny House Retreat~Hot Tub~Cozy

4.98 out of 5 average rating, 44 reviews

The living area features a light, airy design with soft, neutral furnishings including a spacious sofa and armchairs. Natural light enters through large windows, complemented by sheer curtains. A woven area rug adds texture, while a decorative plant brings a touch of greenery to the space.

Home in Navy Point

Navy Point Bungalow near Beaches/ Downtown/NAS

A spacious living room is furnished with a large sectional couch, adorned with colorful accent pillows. A coffee table is centrally positioned, while large windows provide natural light and views of the outside greenery. Decorative curtains frame the windows, enhancing the room's inviting feel.

4.78 out of 5 average rating, 219 reviews

Central Comfort: Home in the Heart of the City

A spacious living area is highlighted by a large bed framed by a simple headboard. A couch and an armchair provide additional seating. Soft light from side lamps enhances the neutral color palette, while a large TV is mounted on the wall opposite the bed.

4.89 out of 5 average rating, 53 reviews

Spacious Studio Close to Everything

A cozy living area features a gray sectional sofa with coral pillows, complemented by a glass coffee table. A large mirror reflects natural light, while sheer curtains frame the window, enhancing the spacious feel of the room.

4.97 out of 5 average rating, 71 reviews

Vibrant Airport 2bdr Central Pensacola Getaway

A vibrant dining area features a round table surrounded by plush turquoise chairs. The walls showcase eclectic patterns, including floral and geometric designs. A chandelier hangs above, illuminating the space, while a green wall with a neon sign adds a whimsical touch.

4.89 out of 5 average rating, 62 reviews

Good Vibes. Fun Downtown Cottage