Places to stay near Shaggy's Pensacola Beach

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Top-rated holiday rentals near Shaggy's Pensacola Beach

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Top guest favourite

A spacious outdoor deck is set with a long table, accommodating multiple guests. Chairs and glassware are arranged neatly for dining. Lush green trees surround the area, offering a relaxed atmosphere, while a glimpse of water can be seen in the distance.

Home in Pensacola

Large Mid-Century Home w/Bay View & Ancient Trees

Large nicely furnished 4/4 home located high on a hill overlooking Escambia Bay in Pensacola. This unique home features a large yard & relaxing views of the bay & towering trees, interesting artwork, 2 huge decks, 2 balconies, 70" big screen 4K TV, large open living & huge master suite. Great location short drive from beaches parks & trails. 10 mins from historical downtown, bars and restaurants. 10 mins to Pensacola Airport 25 mins to Pensacola Beach 28 mins to NAS 1 hour to Fort Walton/Destin.

4.89 out of 5 average rating, 279 reviews

Top guest favourite

A spacious living area is shown, featuring two gray sofas and a sleek television mounted on the wall. Sunlight filters through sliding glass doors, revealing a view of the balcony. A light blue accent chair and a decorative side table complement the setting.

Apartment in Pensacola Beach

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.

4.98 out of 5 average rating, 121 reviews

Top guest favourite

A bright waterfront scene is captured, featuring Little Sabine Bay with reflections shimmering on the water's surface. The view includes marinas with sailboats and yachts, framed by palm trees and gardens, with a pool visible in the foreground.

Apartment in Pensacola Beach

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.

5.0 out of 5 average rating, 164 reviews

Top guest favourite

An aerial view captures the Pensacola Beach Boardwalk and surrounding waterfront, with the sun setting over the horizon, creating a gradient of warm colors. The condo building is visible against the backdrop of the beach and pier, offering a view of the vibrant activity along the coast.

Apartment in Pensacola Beach

Walk to Everything-Best Sunset-Comfy King-Stocked

South Harbour Condo 11th Floor corner unit in the heart of Pensacola Beach! Walk to everything, park and relax. Beautiful waterfront condo directly across the street from casino Beach. The 11th floor has the best views, extra windows, larger layout boasting king in master, bunks & Queen in second room. Best view sunsets on the beach, walking distance to anything you need charter fishing, restaurants, rentals, pier, surfing. Lots of upgrades, everything needed for a week or two or longer!

4.99 out of 5 average rating, 114 reviews

Top guest favourite

A private balcony overlooking calm blue waters and a sandy beach. A circular white table with two accompanying chairs is positioned at the edge, creating a space to enjoy the panoramic views of Pensacola Bay.

Apartment in Pensacola Beach

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.

4.95 out of 5 average rating, 291 reviews

Top guest favourite

The open concept living area features a cream-colored sofa and a round coffee table. A wooden loft area is visible in the background, with warm lighting illuminating the kitchen. A large television hangs on the wall, complementing the bright and welcoming space.

Apartment in Pensacola Beach

Amazing Condo on Bay, Steps from Gulf of America

Everything included! Recently remodeled waterfront condo with vaulted ceilings located on Little Sabine Bay and steps from the Gulf of America. Enjoy coffee and cocktails on an amazing balcony overlooking the Bay. Walk or bike to shopping, dining, and the Gulfside. 1 bedroom condo with a loft. The open concept living/kitchen has a 7' island. Beds include King in master, queen in the loft and a queen sofa bed. 1 covered parking spot . 2 bikes 2 Inflatable paddle boards also included.

4.93 out of 5 average rating, 267 reviews

Top guest favourite

A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.

Apartment in Pensacola Beach

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.

4.99 out of 5 average rating, 157 reviews

Top guest favourite

The living area features a brown leather sofa paired with a wooden coffee table and a patterned area rug. A large television is mounted on the wall, while a dining space is visible in the background, showcasing a bright and open layout with natural light.

Apartment in Pensacola Beach

Bay View Condo on Pensacola Beach at Sand Dollar

Welcome to Seashell Suite at Sand Dollar! This lovely 1 bed/1 bath, water view condo is located on Little Sabine Bay in Pensacola Beach, FL! Relax on the patio as you look out at the tranquil water with the salty breeze blowing in your hair. The white sandy beaches of the Gulf of Mexico are right across the street, the nearest public access less than a 5 minute walk away! You can also easily walk/drive to the bustling boardwalk with shopping and plenty of great restaurants.

4.93 out of 5 average rating, 510 reviews

Guest favourite

A modern kitchen area features white cabinetry with a spacious island, complemented by bar stools. Large windows allow natural light to fill the space while offering views of the surroundings. Outside, a wooden staircase leads to an elevated entryway, illuminated softly at night.

Home in Pensacola Beach

Island Life Beach House! 300ft to water!

The entire vibe of this home is "Island Life". If you're looking for a cozy spot on the beach that will make you feel more like you're at home than a tourist on vacation, this is the place for it. Our cute beach house is located on Pensacola Beach, and the water is within sight from the roomy outdoor deck. There are 2 bedrooms and 1 bathroom, kitchen, living space, outdoor space, and everything you need to enjoy life on the beach! FREE PARKING

4.97 out of 5 average rating, 122 reviews

Top guest favourite

A balcony view features a black table with a wooden pelican sculpture at its center. Surrounding palm trees provide shade while Sabine Bay glistens in the background, creating a serene waterfront atmosphere. Comfortable blue chairs are positioned near the table, inviting relaxation.

Apartment in Pensacola Beach

Gorgeous condo steps from beach!

“Welcome to Island Time” Escape to Pensacola Beach! Beautiful renovated one bedroom condo w/ sleeper sofa on Sabine Bay. You are just across the street from Pensacola Beaches beautiful white sand and blue waters. Walking distance to restaurants & activities. Pensacola Beach is the ideal destination if you are looking for a wide variety of activities. Soak in the sun-drenched days while you enjoy your vacation the way it is supposed to be.

4.96 out of 5 average rating, 206 reviews

Top guest favourite

A spacious bedroom features exposed brick walls and large windows allowing natural light. The king-sized bed is dressed in soft linens with decorative pillows. Nightstands with warm lamps flank each side, while a small vase holds flowers on the bed, enhancing the inviting atmosphere.

Loft in Downtown Pensacola

Palafox Balcony | Staycations/Events | Posh A 2BR

Treat yourself to an unforgettable experience at our second floor Palafox St apartment with a balcony overlooking the action in the heart of our beautiful city. Our spacious 2/2 apartment sleeps up to 10 people comfortably and is the perfect destination for a weeknight concert crash pad, a downtown weekend staycation, wedding parties, family vacation, or an extended executive stay. Enjoy the luxury of a home away from home. Reserve today!

4.96 out of 5 average rating, 295 reviews

Top guest favourite

A charming cottage exterior is presented, featuring a light-colored facade and a gabled roof. A welcoming covered porch is visible, framed by tall trees. Two beach cruiser bicycles are parked on the concrete driveway, inviting exploration of the nearby downtown area.

Cottage in West Pensacola

Eclectic Eco- Friendly Luxe City Cottage

New eco chic cottage features high end touches and appliances in a cozy luxe setting. Sitting on the edge of the downtown jurisdiction, you're never too far away from the action on Palafox Street and a quick jaunt over to the beach. Excellent access to Wahoos Stadium, Sanders Beach, The Oar House, Pensacola Yacht Club, Pensacola Country Club, Joe Patti's, and Pensacola's Naval Air Station.

4.99 out of 5 average rating, 617 reviews