
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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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
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.
4.98 out of 5 average rating, 242 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, 121 reviews
Gulf Breeze getaway w/hot tub, minutes to beach
Welcome to your Gulf Breeze getaway! Perfect for a family vacation, this newly furnished bright and cozy home is located in a peaceful neighborhood surrounded by shady trees. This location is a short 9 minute drive to Pensacola Beach! Local convenient stores and restaurants are also minutes from the home. Be sure to include the dreamy white sands and crystal clear waters of Pensacola Beach into your travel plans. You'll also want to soak in the back yard hot tub to relax at the end of the day!
4.87 out of 5 average rating, 204 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, 114 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, 291 reviews
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, 266 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, 109 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, 156 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, 509 reviews
307 Special Deal ~ Gulf Front ~ Book Oct 17th
Come experience this Beautiful 5 Star Gulf Front Condo, Heated Gulf Side Pool & Hot tub, This Newly Renovated unit offers a Private, Gulf Front Balcony with Amazing Gulf Views, watch Dolphins, Swim in 2 Gulf Side pools, 1 heated, Hot tub on the Gulf. Sleeps 6, Gulf Front Balcony Master on Gulf, 2 BDRM, 2 BA, Master Suite has a luxurious King Size Cloud Lux Tempur-Pedic Bed. Guest Rm 2 has a Euro Top Plush Queen Mattress, LR has a Memory Foam Queen sleeper sofa.
4.97 out of 5 average rating, 144 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, 337 reviews
Welcome to Pura Vida: Top-Floor View & Beach Bliss
4.94 out of 5 average rating, 136 reviews
Island Oasis, 3Bed/2Bath, Pool, & Beach Gear
4.98 out of 5 average rating, 100 reviews
Cozy Bayou Bungalow - just steps from the water
4.96 out of 5 average rating, 287 reviews
Gorgeous condo steps from beach!
4.96 out of 5 average rating, 206 reviews
Book now for spring/summer! Beautiful sound views!
4.97 out of 5 average rating, 116 reviews
Sunrise at Santa Rosa Dunes
4.84 out of 5 average rating, 253 reviews
Gulf Getaway+ Waterfront Views *Fully Updated*
4.96 out of 5 average rating, 243 reviewsFamily-friendly house rentals

4 BR/3 BTH Home In the Heart of Pensacola Beach
4.93 out of 5 average rating, 103 reviews
Beach Home with Wraparound Deck & Path to Sand
4.93 out of 5 average rating, 189 reviews
Backyard Oasis Family friendly Pensacola Beach, FL
4.9 out of 5 average rating, 147 reviews
East Bay Hideaway — A Private Waterfront Escape
4.97 out of 5 average rating, 196 reviews
Great Gulf Breeze Getaway Near Pensacola Beach
4.88 out of 5 average rating, 152 reviews
Fun, sun, sand, and rest. Enjoy your stay with us.
4.93 out of 5 average rating, 123 reviews
Waterfront Sunsets
4.97 out of 5 average rating, 261 reviews
Hot Tub! Game Room! Balconies Views! Steps 2 Beach
4.88 out of 5 average rating, 153 reviewsApartment rentals with air conditioning

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
The Kitchen | Historic East Hill Studio Near Downt
4.95 out of 5 average rating, 100 reviews
Coastal Townhouse Across From Sound
4.94 out of 5 average rating, 120 reviews
The Kelley House | Cozy Fall Suite 3 w/Balcony
4.97 out of 5 average rating, 292 reviews
Charming East Hill Cottage
4.91 out of 5 average rating, 195 reviews
Stylish Place 7 Miles from the Beach/self-check-in
4.94 out of 5 average rating, 143 reviews
The Lazy Dolphin
4.83 out of 5 average rating, 146 reviewsOther great holiday rentals near Shaggy's Pensacola Beach

Eclectic Eco- Friendly Luxe City Cottage
4.99 out of 5 average rating, 613 reviews
Pensacola Beach South Harbour
4.94 out of 5 average rating, 33 reviews
Pet Friendly*Wave n' Sea at Deepwater Cove!
4.74 out of 5 average rating, 42 reviews
South Harbour 8B - 𝑲𝒂𝒊 𝑴𝒂𝒌𝒂𝒏𝒊
5.0 out of 5 average rating, 18 reviews
11th Floor Paradise on Pensacola Beach
4.93 out of 5 average rating, 92 reviews
Location Location Close to everything Beach & Play
4.92 out of 5 average rating, 62 reviews
Cozy & Elegant Condo with Balcony 2 bed/2 baths
5.0 out of 5 average rating, 13 reviews
Blue Crab Condo in the Heart of Pensacola Beach
4.86 out of 5 average rating, 42 reviewsDestinations to explore
- Destin Beach
- Gulf Shores Public Beach
- Crab Island
- Destin Harbor Boardwalk
- Perdido Key Beach
- Opal Beach
- OWA Parks & Resort
- Village of Baytowne Wharf
- Henderson Beach State Park
- 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
- Waterville USA/Escape House
- The Track
- Adventure Island
- Gulfarium Marine Adventure Park
- Pensacola Bay Center





