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Holiday Rentals near Timpoochee Trail

Begins where Highway 30A separates from US Highway 98, Inlet Beach, Florida 32459
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    Travellers to Inlet Beach are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 32 Rentals in Inlet Beach
    Seaside family home w/ ocean views, shared pool, & plenty of room!1 / 55
    (1)Excellent
    0.3 kilometres from Timpoochee Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    0.0 kilometres from Timpoochee Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    0.3 kilometres from Timpoochee Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    0.2 kilometres from Timpoochee Trail
    10 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    Smoking allowed
    About this property
    Far from simply an ordinary vacation rental home, Gilligan’s Island is a veritable estate! With a main home and guest home totalling 10 bedrooms and 10 bath and accommodating up to 28, this compound is a perfect size for an extended family reunion, or several families travelling together. The...
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    Inlet Beach, Florida Panhandle
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 28
    0.2 kilometres from Timpoochee Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gated, private community with large pool and quick beach access. Privacy South of 30A Adjacent to Rosemary Beach, and South of 30A, our 2250 sq ft gated community beach home has been updated and professionally decorated. Surrounded by dense vegetation, there is a surprising amount of privacy for...
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    Inlet Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.2 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Just Steps from Rosemary Beach in Inlet Beach FOREVER FRIDAY II CARRIAGE HOUSE is furnished with a sofa and a 32 inch Flat Screen TV in the living area, 18 inch Flat Screen in the Queen bed sleeping nook and a reading lamp. The small, but well equipped, efficiency kitchen has a full stove and oven,...
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    Inlet Beach, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.3 kilometres from Timpoochee Trail
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    About this property
    *This Luxury rental is located in a private Community of 10 homes that share a gulf front pool and private beach of their own.Located outside the Rosemary Beach® community. No access to Rosemary Beach community pools or beach walkovers. Inlet Beach Luxury Soak up the Florida sunshine in the light...
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    Inlet Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    0.2 kilometres from Timpoochee Trail
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    SAND DEL MAR is in Inlet Beach, conveniently located on the first street east of Rosemary Beach. The Main House has a great bedroom layout with 3 King Bedrooms, 1 Queen Bedroom and 2 Bunks with 4 Twins. There a beautiful 22' x 12' Private Pool (can be heated for an additional fee) on the property....
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    Inlet Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    0.2 kilometres from Timpoochee Trail
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    *Located steps outside the Rosemary Beach® community. No access to Rosemary Beach community pools or beach walkovers* SOUTHERN SEASIDE COTTAGE is an Open Concept beach home with a lovely fully equipped kitchen with plenty of space for cooking for a large group. The 1st floor opens out to a large...
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    Inlet Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    0.2 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    *Located outside the Rosemary Beach® community. No access to Rosemary Beach community pools or beach walkovers* Just Steps from Rosemary Beach, in Inlet Beach SOUTHERN SEASIDE CARRIAGE is furnished with a 32' Flat Screen TV in the living area, Queen bed sleeping area and a reading lamp. The...
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    Inlet Beach, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Timpoochee Trail
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    About this property
    Located a stone's throw from Rosemary Beach The Best of Both Worlds The whole family will enjoy Southern Seaside Cottage & Carriage House! Located in on the eastern end of Scenic Highway 30A, this property offers all of the amenities you could ever want in a beach rental. You know you've arrived...
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    Inlet Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    0.3 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
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    About this property
    Hardwood floors and neutral tones are accented with pops of color throughout this cozy coastal retreat conveniently located near the Conquina Pool, Main Street and of course, the white sand and emerald waters of the South Walton’s world-famous beaches. An ideal beach getaway, the luxurious Abaco...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    0.3 kilometres from Timpoochee Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hardwood floors and neutral tones are accented with French Country decor throughout this outstanding coastal abode conveniently located near the Coquina Pool, Main Street and of course, the white sand and emerald waters of the South Walton’s world-famous beaches. An ideal beach retreat, the...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Blue Heron Cottage & Carriage House - Comfort At Its Finest!!1 / 37
    (1)Excellent
    0.3 kilometres from Timpoochee Trail
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 27 April 2017
    This property is absolutely perfect. We even used a lot of the elements from this house in our kitchen renovation. As we drove up my teenager daughter who has been to rosemary...
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    About this property
    Take retreat at the Blue Heron Cottage in Rosemary Beach, the quintessential luxury beach home. The Cottage features 3 bedrooms, 3.5 baths and upgrades throughout like stainless steel appliances, marble counters in the kitchen and baths, hardwood flooring throughout, Green Egg grill, and not to...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    0.3 kilometres from Timpoochee Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this warm, luxurious beach cottage, a great home for creating memories with your family and friends. Begin your days viewing the sun rise over the Gulf from the loft balcony and complete them with the amazing sunsets from the dining room and park balcony. The first floor includes a...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.3 kilometres from Timpoochee Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ~ Welcome to your home away from home! This beautiful newly remodeled and refurnished family friendly beach home, 'All 4 Fun,' is located in the heart of Luxurious Rosemary Beach, and in the perfect location '4' an amazing family vacation! Location is key in this wonderful home, it is in close...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.3 kilometres from Timpoochee Trail
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    About this property
    The livin’ is easy at the New Orleans inspired Something Blue Cottage. The backyard oasis holds something dear for each member of your family. The inground pool with water feature makes for hours of cool relaxation for all. Soak up the Vitamin D in one of the sun loungers or enjoy a meal or cool...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    0.3 kilometres from Timpoochee Trail
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    As the perfect petite add-on to the Something Blue Cottage, the Something Blue Carriage House can accommodate up to 6, either in conjunction with the main home or as a standalone vacation property. Your private cottage will feel like a treehouse, as you relax on your private patio overlooking the...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.3 kilometres from Timpoochee Trail
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This beautiful Rosemary Beach home is the epitome of coastal luxury. The ultimate vacation getaway, this incredible home is filled with natural light from the Florida sun. Every detail has been well thought out in this home from the designer furnishing to the beachy decor. A stunner from the moment...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.3 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Whether as additional accommodations to the on-site Highland Cottage or a luxury getaway all by itself, the Highland Carriage House provides an elegant simplicity that will both charm and delight you. Located just steps from the Racquet Club, tennis courts and Sky pool, the Highland Carriage...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This newly-renovated Rosemary Beach carriage house is well-designed allowing for plenty of natural light from the Florida sun. The high-end furnishings and decor give this coastal home a relaxing and luxurious feel. You’ll get beach vibes the second you cross the threshold of this serene home. A...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Timpoochee Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious carriage house near Sky Pool, Fitness Center and Racquet Club Old Florida Style Relax in the Old Florida style ambiance with modern comforts to aid in a pleasant stay. Enjoy the nearby pools and tennis courts, and the Gulf is but a short walk through the picturesque architecture of...
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    Rosemary Beach, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.3 kilometres from Timpoochee Trail
    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Children's Pool
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    IMAGINE....custom crafted perfection from Benecki homes - the builder who brought you the Coastal Living Home in 2012. Some of the sumptuous details you will find in Abaco Cottage & Carriage House are: Venetian plaster, wood beam ceilings, limestone & marble kitchens and baths, wood walls, ceilings...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
    Bennett Carriage House1 / 6
    (1)Terrible
    0.3 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This home is truly a beach lover's dream. With its bright colors and cheery decor, it's sure to give you pleasant dreams of surf, sand and sun. The Bennett Carriage House features a loft bedroom with a queen bed and spiral staircase access. The open kitchen, living and dining areas are...
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    Rosemary Beach, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Timpoochee Trail
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. *** sociis natoque penatibus et magnis dis. Ullamcorper a lacus vestibulum sed arcu non odio. Risus commodo viverra maecenas accumsan lacus vel. In hac habitasse platea...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Timpoochee Trail
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
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    • Washer
    • Air Conditioning
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfort truly meets chic in this luxury Benecki home, steps away from the Rosemary Beach® Fitness Center and Racquet Club. Complete with three floors of ultimate luxury, soothing neutral tones on the Venetian plaster walls greet you upon entry. Eyes avert upward, showcasing a grand staircase...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    0.3 kilometres from Timpoochee Trail
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. *** sociis natoque penatibus et magnis dis. Ullamcorper a lacus vestibulum sed arcu non odio. Risus commodo viverra maecenas accumsan lacus vel. In hac habitasse platea...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    0.3 kilometres from Timpoochee Trail
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inspired by classic Ralph Lauren® style Upon entering, splashes of blue from the entry way table's ginger jars will bring your eyes searching up the adjacent Venetian plaster walls filled with sporty polo prints. This is just the beginning of the elegantly appointed cottage furnished by Atlanta's...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    0.3 kilometres from Timpoochee Trail
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Kid friendly
    Smoking allowed
    About this property
    Close to Coquina Pool! Dejarnette Carriage House is great for a small family or a couple. The dark wood floors and light color accents give the carriage house a very fresh and airy atmosphere. A studio-style first floor features a queen size bed and love seat situated in front of the electric...
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    Rosemary Beach, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.3 kilometres from Timpoochee Trail
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    About this property
    South of 30A Perfectly situated on the south side of Rosemary Beach and steps from the Gulf, this spectacular, one-of-a-kind beach house is a rare and ultimate find. As you enter the gracious courtyard, shaded by stunning crepe myrtles, you will understand the treasure chest of wonderful beach...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    0.3 kilometres from Timpoochee Trail
    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    Kid friendly
    Smoking allowed
    About this property
    An entry way of silky, white Venetian plaster walls stretch out from white peacock pavers turning focus to Bentley Beach Cottage's open first floor living space. The sunken living space houses the kitchen replete with Thermador refrigerator, La Conrue range and Bosch dishwasher. Bar seating for...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
    0.3 kilometres from Timpoochee Trail
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Centrally located on the beach side of 30a On the Gulf-side of Rosemary Beach lies the Bennett Cottage, a family-style cottage accommodating up to twelve - perfect for multiple families or one large family with grandparents joining along for the fun. Bennett Cottage is truly a beach lover's...
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    Rosemary Beach, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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