
Places to stay near Shaggy's Pensacola Beach
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Shaggy's Pensacola Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

4 BR/3 BTH Home In the Heart of Pensacola Beach
Welcome to Fireball Island! Recently updated, professionally decorated 4 BR/3 BTH home with a modern beach vibe. Just a 5 minute walk to the beach and restaurants/shops! Just across the street, there's a 2 block direct path to beach access, which puts you right at the beginning of the quieter part of the beach, away from the major condos/hotels. Conveniently located just past the Pensacola Beach commercial strip, you'll enjoy a short walk to all the best shops, bars, and restaurants in town.
4.93 out of 5 average rating, 102 reviews
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, 278 reviews
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, 120 reviews
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
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, 112 reviews
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, 288 reviews
Kayaks & Paddle Boards SunRise & SunSet Views
Welcome to SunnySide UP! The serene 2 bedroom 2.5 bath with water view is located on Little Sabine Bay in Pensacola Beach, FL. Relax on the patio as you look out at the tranquil water as you sip your morning coffee or glass of wine in the evenings. The white sandy beaches of the Gulf of Mexico are right across the street, the nearest public access less than a 5 minute walk! You can also easily walk/drive/trolley to the bustling boardwalk with shopping and plenty of great restaurants.
5.0 out of 5 average rating, 108 reviews
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, 153 reviews
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, 508 reviews
Hot Tub! Game Room! Balconies Views! Steps 2 Beach
Welcome to Island SOS, by Stayawhilewithus! A newly renovated coastal escape, just steps from Pensacola’s Baby Beach and a short walk from the stunning Gulf beaches! Enjoy breathtaking views of the Santa Rosa Sound, catch the Blue Angels soaring overhead, and unwind in style with our hot tub, brand-new game room, and spacious outdoor seating areas. With plenty of parking space for your boat or RV, this home is perfect for families, snowbirds, and group getaways.
4.91 out of 5 average rating, 149 reviews
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
4.99 out of 5 average rating, 116 reviews
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, 205 reviewsPopular amenities for holiday rentals near Shaggy's Pensacola Beach
Other top sights near Shaggy's Pensacola Beach
Apartment rentals with wifi

Quiet Pensacola Beach Condo Sleeps 4
4.84 out of 5 average rating, 336 reviews
Amazing Condo on Bay, Steps from Gulf of America
4.93 out of 5 average rating, 266 reviews
Welcome to Pura Vida: Top-Floor View & Beach Bliss
4.94 out of 5 average rating, 136 reviews
307 Stunning Gulf Views ~ Pools ~ Book Sept 26th
4.97 out of 5 average rating, 144 reviews
Pelican's Perch @ Villas on the Gulf
4.95 out of 5 average rating, 178 reviews
Cozy Bayou Bungalow - just steps from the water
4.96 out of 5 average rating, 282 reviews
Gulf front @ Emerald Ise, Pensacola Beach~HEATED p
4.86 out of 5 average rating, 154 reviews
Classic Pensacola Beach Condo!
4.93 out of 5 average rating, 194 reviewsFamily-friendly house rentals

Beach Home with Wraparound Deck & Path to Sand
4.93 out of 5 average rating, 186 reviews
Backyard Oasis Family friendly Pensacola Beach, FL
4.9 out of 5 average rating, 146 reviews
The Cottage By The Bay
4.99 out of 5 average rating, 142 reviews
Fun, sun, sand, and rest. Enjoy your stay with us.
4.93 out of 5 average rating, 121 reviews
Great Gulf Breeze Getaway Near Pensacola Beach
4.87 out of 5 average rating, 151 reviews
Beach Barn | 5min to Pcola Beach • Full Kitchen
4.91 out of 5 average rating, 325 reviews
Gulf Breeze getaway w/hot tub, minutes to beach
4.87 out of 5 average rating, 201 reviews
Airport Convenience | Pets AOK | Multiday Discount
4.93 out of 5 average rating, 148 reviewsApartment rentals with air conditioning

Coastal Townhouse Across From Sound
4.94 out of 5 average rating, 118 reviews
Ocean Tranquility label by guest“Heaven on Earth”.
4.95 out of 5 average rating, 131 reviews
Mid-Century Breeze
4.9 out of 5 average rating, 166 reviews
Downtown Intimate Light-Filled Getaway
5.0 out of 5 average rating, 268 reviews
Charming East Hill Cottage
4.91 out of 5 average rating, 194 reviews
Classic Coastal Getaway in Downtown + Free Parking
4.98 out of 5 average rating, 117 reviews
Stylish Place 7 Miles from the Beach/self-check-in
4.94 out of 5 average rating, 143 reviews
Entire studio space is private, clean & relaxing.
4.96 out of 5 average rating, 217 reviewsOther great holiday rentals near Shaggy's Pensacola Beach

Pensacola Beach South Harbour
4.97 out of 5 average rating, 30 reviews
Last Minute August Escape | Pensacola Beach
4.67 out of 5 average rating, 18 reviews
11th Floor Paradise on Pensacola Beach
4.93 out of 5 average rating, 92 reviews
Blue Crab Condo in the Heart of Pensacola Beach
4.85 out of 5 average rating, 41 reviews
On the Beach! 2Bedroom/2Bath CondoFor6-Kitchen-SHB
4.73 out of 5 average rating, 83 reviews
South Harbour 8B - 𝑲𝒂𝒊 𝑴𝒂𝒌𝒂𝒏𝒊
5.0 out of 5 average rating, 17 reviews
Fabulous 2 bedroom end unit at South Harbour - 4A
5.0 out of 5 average rating, 7 reviews
Rare Waterfront Find! Stay 4/25-4/28 or 6/14-6/21
4.91 out of 5 average rating, 11 reviewsDestinations to explore
- Destin Beach
- Gulf Shores Public Beach
- Crab Island
- Destin Harbor Boardwalk
- Perdido Key Beach
- Opal Beach
- OWA Parks & Resort
- Henderson Beach State Park
- Village of Baytowne Wharf
- Flora-Bama Lounge
- Gulf State Park
- Navarre Beach Fishing Pier
- The Hangout
- Johnson's Beach, Gulf Islands National Seashore
- Alabama Point Beach
- HarborWalk Village
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- The Track
- Waterville USA/Escape House
- Adventure Island
- Pensacola Bay Center
- Phoenix 5 Vacation Rental Condominiums





