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Seaside Vacation Rentals

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    Travelers to Seaside are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 112 Rentals in Seaside
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Waterside in Seaside - 5108581 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Reviewed July 20, 2016
    This is an excellent house for the beach. It is on the corner of E. Ruskin and 30A, roughly 45 seconds from the pavilion to the beach. The Seaside city center is roughly 60...
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    Welcome to Waterside (11 East Ruskin) This three bedroom, three bath shaded retreat is just steps to the beach. Located at the corner of East Ruskin Street and 30A, Waterside is directly across from the private East Ruskin Pavilion beach access. You can sun all day and return home to the cool,...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    73 Odessa Street 5-night minimum during spring break and summer Settle right in to Furs, Fins and Feathers and take advantage of the porch swings, sun deck and its nearby location to Westside Pool and the Gulf. This classic Seaside beach cottage includes a dine-in kitchen, a large living area with...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    498 Forest Street 5-night minimum stay required during spring break and summer Featured in South Walton Life, you will love that this cottage is just a five-minute walk to everything. On the first floor, there is a furnished front porch with a swing, a living area with a queen sleeper sofa, a...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    40 Venice Circle 5-night minimum stay required during spring break and summer Splendor in the Sand is a well-appointed 3-bedroom/3.5 bath home, conveniently located near the Adult and Family Pools/Fitness Center. On the first floor, there is a large den, a king bedroom with private bath, as well as...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Satellite TV
    • Balcony
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    • DVD Player
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    Above the Crowd – 25 Central Square # 301 – Seaside, FL Above the Crowd is a sophisticated and stylish two story penthouse apartment that offers the best of new urbanism living. This unit was completely renovated in 2016 and has all new floors, kitchen, additional bathroom, renovated existing...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    751 Forest Street 5-night minimum stay required during spring and summer Comfort, class, and conveniences- Southern Splendor offers it all. The front entry leads you into a fully-equipped kitchen with a gas stove and bar seating, as well as a living area, a dining area and access to the screened-in...
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    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Internet Access
    • Balcony
    • Washer
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Center Stage – 63 Central Square – Seaside, FL End of Summer Special - 20% Off! Appropriately named “Center Stage”, this sophisticated town center apartment is ideally located in the heart of Seaside. Center Stage is directly in front of the Seaside Amphitheater where you can watch weekly plays...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    "What was not to enjoy!? The proximity of the cottage to the center of town was perfect, it was nice and clean, and we will be back!" --Shore is Fun Guest Survey, 2017 32 Pensacola Street 5-night minimum stay required during spring break and summer Shore is Fun is conveniently located just a short...
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    Seaside, Florida Panhandle
    Rental Home - 3 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 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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    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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    Margarita Days1 / 21
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 2012
    My husband and stayed here for a couple days without our kids. The size is perfect for 2 people. Since it is only one bathroom I would not recommend for families with older...
    Reviewed July 16, 2012
    A very cozy cottage, perfect for a vacationing couple. No more than 2 people can be here comfortably though. We spent our honeymoon here and had a lovely time. Literally across...
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    Margarita Days is a charming 2-story beach cottage tucked behind Bella Vista on Tupelo Street in Seaside. It's the perfect getaway for a couple or small family as it sleeps 2 to 4 with a queen bedroom and full bath on the first floor, and a sleeper in the living area for 2 children if needed. It...
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, 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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    Station, The1 / 15
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Reviewed November 16, 2015
    What a great spot. One block to the shores or to old town. Fabulous 4 bedroom home that was nicely compartmentalized for multiple families with plenty of shared space and...
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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, 3 Bathrooms, Sleeps 6 Quick View
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    45 Central Square 5-night minimum stay required during spring break and summer Far Niente is short for “doing nothing” and this is the perfect place for doing exactly that! This grand two-story penthouse is located above Central Square in Seaside, offering panoramic views of the town and the Gulf...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Welcome to Karibu in Seaside (111 Grayton Street) Karibu is the delightful guest cottage to Hakuna Matata. Both are conveniently close to the Westside Pool and only a two minute walk to the beach. Karibu opens into a small courtyard with barbecue grill, and is privately accessible by one of...
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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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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    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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    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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    A Ritz Sea Inn1 / 15
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed November 28, 2016
    The location of this property is hard to beat. It's one street behind the Seaside square with a plentitude of shopping and dining. It's directly across the street from the beach...
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    29 Quincy Circle 3-night minimum stay required during spring break and summer Just steps away from the beach and located in the Medical/Arts building of Central Square, this spacious two-bedroom is a metropolitan masterpiece. Twelve-foot high ceilings and dark hardwood floors open the space and...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    561 Forest Street 5-night minimum stay required during spring break and summer Soulshine is conveniently located just minutes away from Ruskin Place Artist Colony and the Seaside Chapel. This cottage has lots of floor space and comfortably embraces large families. The first floor includes a...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Grill
    • DVD Player
    • Washer
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    Persuasion - 42 Savannah Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Beautiful Persuasion is situated in the quaint town of Seaside, Florida. Located in the panhandle, Seaside resembles a modernistic approach to 'old Florida', with...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    25 Central Square, #302 This two-story one-bedroom penthouse is the definition of cosmopolitan living at the beach. Boasting a spectacular view of the Gulf of Mexico and overlooking Seaside’s Central Square, this grandeur accommodation is fully equipped with a kitchen, dining area, half bath and...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2376 East County Hwy. 30A Find out for yourself why this home has more repeat guests than any other in Seaside, Florida! Savannah Sands is a classically designed Gulf front beauty with stylish West Indies décor throughout. As you enter the house, on the first floor is the master king bedroom with a...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    "It was wonderful! The house worked so well for our group of twelve. It was very clean, and we enjoyed ourselves very much." --Guest Survey, 2017 142 East Ruskin Street Located near the pools, fitness center and tennis courts, Big Pink is also just a short walk to Ruskin Place, Central Square and...
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    Seaside, Florida Panhandle
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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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    6 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    147 Grayton Street The Old Natchez Compound is conveniently located across from the Westside Pool and combines three separate living areas- perfect for a large family or group. On the left side of the compound, Oak Creek Annie’s (OAKCR) speaks of rustic times and folklore with a queen bedroom and...
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    Seaside, Florida Panhandle
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 13
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • DVD Player
    • Satellite TV
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    842 Forest St. 5 night minimum stay required during spring and summer Named after the owners' favorite Jimmy Buffet song, Banana Republic is a 3 BR, 2.5 bath stylish combination of tropical and mid-century décor that sleeps 7 and is located near the Westside community pool in Seaside, Florida. The...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    152 East Ruskin Street Located near Ruskin Place Artist Colony and the beach, Somewhere is a delightful cottage to experience Seaside. Walk through Somewhere’s private canopied entrance onto its screened-in porch where you’ll find a peaceful and uplifting decor, offering a cozy living room,...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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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, 3 Bathrooms, Sleeps 8 Quick View
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    Welcome to Hakuna Matata at Seaside (111 Grayton Street) Leave your worries at home. In fact this home's name means "no worries" and our guests will have none while vacationing here! Upon your first step onto the long front porch, you will be tempted to stop and rock and relax in the inviting...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    39 West Ruskin Street 5-night minimum stay required during spring break and summer A perfect place to escape everyday stresses, Take Five is located a few minutes from the beach and to Seaside's Central Square. This stylish cottage has a nice and cozy living room, a dining area and a fully-equipped...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    123 Grayton Street 5-night minimum stay required during summer Midsummer Night's Dream is not exactly what you'd find in Shakespeare, but definitely what you'd find in Seaside, FL. Located across from the Westside Pool and only a block from the beach, a large screened-in front porch greets you into...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    "Great house, town, beach, food. This house was a very nice place to say." --Starry Night Guest Survey, 2017 13 Odessa Street 5-night minimum stay required during spring break and summer This spectacular cottage is located directly across the street from the beach. The first floor includes all...
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    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
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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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    Location Information
    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Kid friendly
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    "The cottage was in a great location and is a really nice place to be." --Whatcha Dune Guest Survey, 2017 608 Forest Street 5-night minimum stay required during spring break and summer Whatcha Dune is family-friendly cottage located near the Seaside Chapel, directly across from Forest Street Park....
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    Location Information
    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2038 East County Hwy. 30A 5-night minimum stay required during spring break and 7-night minimum in summer. No children under the age of 12. It you are looking for a great panoramic view of the Gulf, Sugaree is the place to be. This beachfront beauty encompasses everything from classy beach décor to...
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    Location Information
    Seaside, Florida Panhandle
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Welcome to Crisobel (52 Odessa Street) From the front porch swing to the rooftop deck, Crisobel offers our guests an unparalleled Seaside beach experience. From the first moment you enter the home you’ll know that it’s been designed to create a backdrop for the perfect family vacation. Recent...
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    Location Information
    Seaside, Florida Panhandle 32459
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Seaside, Florida Panhandle
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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