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Seaside Vacation Rentals

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    Travelers to Seaside are booking October dates now. Secure your vacation rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    2110 East County Hwy 30A 5-night minimum stay required during spring break and 7-night minimum in summer Located on the Gulf side of 30A, Beside The Sea features expansive windows and high ceilings, providing guests with gorgeous Gulf views. The first floor includes a master king bedroom with a...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    'We enjoyed this home so much. It was so clean and well kept, we loved the atmosphere and everything being so close by. Thank you for sharing your home!' --Our Place Guest Survey, 2017 652 Forest Street Our Place By the Sea is a lovely, spacious 1-bedroom home with great porches, a nice patio deck,...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    'We LOVED the home - it was the perfect fit for our family! We can't wait to visit again and stay here!' -- Fleur de Lis Guest Survey, 2017 66 Seaside Avenue Saturday-to-Saturday stay required during spring break and summer; 3-night minimum stay required remainder of the year With beach-inspired...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    109 West Ruskin Place Saturday-to-Saturday stay required during spring break and summer Conveniently located behind the Ruskin Place Artist Colony and near the shops and restaurants of Central Square, Plum Lucky is the combination of two well-appointed cottages--Plum Lazy and Plum Crazy--making...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    640 Forest Street 3-night minimum stay required during spring break and summer, please no children under the age of 5 Named by its owners from Mississippi, the Magnolia State, Suite Magnolia I is a stylish and comfortable duplex-style cottage with a shared front porch with Suite Magnolia II. On the...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    32 Pensacola Street Please no children under that age of 9 Takin It E-sea, located down a short footpath, is the guest house for the main cottage Shore is Fun. Ideally situated, you are just a short stroll from the acclaimed white-sand beach and emerald-green waters of the Gulf. The first floor of...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    2120 East County Hwy. 30A Limited Saturday-to-Saturday stay during peak summer season; please no children under the age of 3 This exclusive residence has been the cover story for several publications including Architectural Digest, Coastal Living, The Coastal Cottage, 30A Style and more. Recently...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    15 Natchez Street 5-night minimum is required during spring break and 7-night minimum in summer Four the Girls is just 100 steps from both the beach and the Westside Pool. This home has been lovingly decorated and maintained and will be your new favorite vacation spot! The first floor welcomes you...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    764 Forest Street 5-night minimum stay required during spring break and summer;Saturday to Saturday required during July 4th holiday week Located near the Westside Pool, the beach and Central Square, Mojo Biblio is a unique home with an open, airy and spacious floor plan and an extensive private...
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    Seaside, Florida Panhandle
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    119 Quincy Circle 4-night minimum stay required during spring break and summer PET FRIENDLY As one of the only dog-friendly rentals in Seaside, Cherished View is the combination of the townhouse, Cherished by the Sea, and the penthouse, Room with a View. With its prime location adjacent to Ruskin...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2454 East County Hwy. 30A Please no children under the age of 5; 5-night minimum stay required during spring break and summer A lovely, colorful home with lots of windows to enjoy the Gulf and Seaside views, not to mention porches and patios on every level, Toye Cottage is one of those amazing...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    15 Tupelo Street 3-night minimum stay required during spring break and summer; please no children under the age of 12 This cottage conveniently opens onto both 30A and Tupelo Street and is just steps to the beach. Once the permanent residence of The Modicas (of Modica Market), Sip 'n Dip is a...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    127 Seaside Avenue 5-night minimum stay required during spring break and summer Located near the Adult/Family pools, tennis, and croquet recreational facilities, String of Pearls is a classic, yet inviting cottage with its antebellum columns and large open furnished front porch. Walking through the...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    55 Central Square 4-night minimum required during summer; 3 night minimum remainder of year Alta Vista is conveniently located in the center of town and is stunning from wall to wall. This recently renovated townhouse includes an oversized master bedroom that is elegantly furnished with a king bed...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    'Very comfortable cottage. Love the tower room on top!' --O Happy Day Guest Survey, 2017 61 Savannah Street 5-night minimum stay required during spring break and summer O Happy Day is a charming cottage that will have you feeling happy all day long. Enter and find a whimsical open living, dining,...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    'We had an awesome experience. We stayed in this same cottage many, many years ago and very pleased to see the updates the owners had made. Nicely done!' --Moon Shine Guest Survey, 2017 62 Pensacola Street 5-night minimum stay required during summer Moon Shine is a great family cottage and the...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    36 East Ruskin Street 3-night minimum stay required during spring break and summer Conveniently located, Sweet Potato is just a short stroll to the beach. This cozy cottage includes a nice screened-in front porch with rockers, a large open living room with dining area, a fully-equipped kitchen and...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    204 Ruskin Place Please no children under that age of 18 The Conservatory is an exquisite 1,600 sq. ft. penthouse that features panoramic views of Seaside, FL from the rooftop, which also includes a hot tub. The master bedroom suite is highlighted by a king bed and an oversized bath with large tub...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Station, The1 / 15
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    31 Smolian Circle Saturday-Saturday stay required during summer; 3-night minimum stay required remainder of the year Your train has finally pulled into 'The Station' when you spend your Seaside, FL vacation in this cottage. Located just minutes from the Westside pool, the beach, and downtown, this...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    'Lovely cottage. It was perfect for us! We didn't realize we would have maid service - they were friendly and did a good job. We had a great time.' --Southern Exposure Guest Survey, 2017 2368 East County Hwy. 30A 6-night minimum stay required during summer; 3-night minimum stay required during New...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2326 East County Hwy. 30A Love Me Tender, Love Me True is located right on Scenic 30A, near Central Square and just 32 steps to the East Ruskin Beach Pavilion, one of Seaside's most photogenic beach walk-overs. Complete with beautiful fixtures, upper-level vaulted ceilings and views of the Gulf,...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    75 Tupelo Street 5-night minimum stay required during spring break and summer Sundance is a large beach cottage with a casual feel and natural tones throughout. Entrance is through a cozy screened-in porch where you will find a living area full of windows for lots of natural light, a dining area, a...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    47 Western Lake (Watercolor) 5-night minimum stay required during spring break and summer Located across from the beach, Masterpiece is an expertly decorated home with custom fabrics, original artwork, state-of-the-art appliances and beautiful dark wood floors. The first floor includes a large...
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    Seaside, Florida Panhandle
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    As Luck Would Have It – 123 Quincy Circle – Seaside, FL “As Luck Would Have It” is a sophisticated 4-story townhome situated in Ruskin Place Park in the heart of Seaside, Florida. With two bedrooms and two and one half baths, this elegant art-filled home sleeps six. Multiple porches overlook the...
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Beachfront Condo with 10' ceilings & King bed1 / 21
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • Ocean Views
    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    This unit is designed as an ADULT ONLY/NO PETS personal vacation residence (couple's or ladies get-away) for 2 persons over the age of 25 only. We have been owners at this location since the 1980's and our original building was destroyed by Hurricane Dennis. If you are interested in the fill...
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Tuscany – 210 W. Ruskin Place – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Tuscany is a spacious, stately townhome perfectly located in the heart of Ruskin Place Artist Colony. It has 2 bedrooms and 2.5 baths and sleeps up to 7 people. The...
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Gift by the Sea - Gulf front Honeymoon Cottage1 / 24
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Satellite TV
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Gift by the Sea-Beachfront 9 – 2088 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferson as he built Monticello. These...
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Bewildered1 / 27
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Bewildered - 25 Central Square #306 - Seaside, FL Bewildered is a spacious two story penthouse apartment that offers the best of new urbanism living. Located on the third and fourth floor of the 25 Central Square Building in the heart of Seaside, this unit offers panoramic Gulf views that can be...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront 101 / 27
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Parking
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Beachfront 10-Honeymoon Cottage – 2070 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferson as he built Monticello....
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sea Sabella1 / 32
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • DVD Player
    • Internet Access
    • Washer
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Sea Sabella – 2314 E. County Hwy 30A – Seaside, FL This luxurious three story home has fifty feet of Gulf frontage and features a beautiful and spacious floor plan. Sea Sabella's specially milled sunken cypress siding was reclaimed from some of North Florida's own rivers and makes the house a...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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