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Holiday Rentals in Seaside, FL

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    Travellers to Seaside are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 24
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Above the Crowd – 25 Central Square # 301 – Seaside, FL Fall and Winter Special. Rent a minimum of 3 nights and receive an additional night free or book a 1 week stay and get 20% off the weekly rate. Valid 9/5/16-3/10/17 excluding Holidays. Above the Crowd is a sophisticated and stylish two story... View all property information
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    Seaside, Florida Panhandle
    1 / 32
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Seaside, Florida Panhandle
    5 of 5 stars Reviewed 12 May 2015
    Great location, immaculate house-fully equipped, and wonderful views. The best rental service I have ever had- they think of everything!! Certainly will return! Only suggestions...
    5 of 5 stars Reviewed 4 June 2014
    This house is spectacular! The whole thing was so well thought out and decorated and would not have changed a thing! One of my most favorite stays in seaside. It is worth the...
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2336 East County Hwy. 30A 3-night minimum stay required during spring break and summer Located on scenic 30A, just steps away from the beach and offering spectacular views of the Gulf of Mexico, this two-story full-service cottage is picturesque, with an abundance of wall windows welcoming the... View all property information
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    Seaside, Florida Panhandle
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    19 Rosewalk 3-night minimum stay required during spring break and summer Mis B’Haven is tucked away in Rosewalk, a cluster of quaint cottages with a pedestrian footpath meandering through a thick grove of oaks trees. This cozy and charming cottage features tongue and groove walls throughout in a... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
    1 / 14
    4.5 of 5 stars (16) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    Seaside, Florida Panhandle
    4 of 5 stars Reviewed 2 November 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...
    4 of 5 stars Reviewed 16 July 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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    1 / 15
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    485 Forest Street Colors A compound is Colors 1 & 2 combined- perfect for large families. Colors A is just a short walk to the beach, swimming pools, fitness center, and the Children’s Park and features a large screened-in front porch, six bedrooms and four bathrooms. The first floor offers two... View all property information
    Location Information
    Seaside, Florida Panhandle
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    1 / 28
    4.5 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Waterfront
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    About this property
    Rome Prize winning architect Walter Chatham built this special beach home, and the same it was on the cover of Architectural Record as the magazine “House of the Year,' and was awarded the prestigious “Award of Excellence” by the National AIA. Featured on the covers of 30A, Florida Architecture,... View all property information
    Location Information
    Seaside, Florida Panhandle
    4 of 5 stars Reviewed 18 July 2014
    This is a amazing house with a contemporary design and tons of great features, but the house was designed for its wow factor and not for comfort. Rent this place if you want to...
    5 of 5 stars Reviewed 20 March 2013
    My husband and I spent a wonderful week in this exquisite beach home; we loved it! Artistic and modern in design; equipped with many extra amenities and features. We would highly...
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    59 West Ruskin 3-night minimum stay required during spring break and summer Spin Echo is a well-appointed cottage located near the Seaside Lyceum and within walking distance to the sugar-white sand beach, as well as to shopping and dining in Central Square. On the first floor, you will find a hall... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
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    About this property
    Firefly - Beachfront 8 – 2094 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 Gulf... View all property information
    Location Information
    Seaside, Florida Panhandle
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • Porch
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    • Pet-friendly
    • Child-friendly
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    • x
    About this property
    Coasting in Style – 25 Central Square #304 – Seaside, FL Fall and Winter Special. Rent a minimum of 3 nights and receive an additional night free or book a 1 week stay and get 20% off the weekly rate. Valid 9/5/16-3/10/17 excluding Holidays. Coasting in Style is a sophisticated and spacious two... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    53 West Ruskin Street "When I walked into my cottage, I understood why it was named 'This Side of Paradise.' Everything was perfect ... convey[ing] a coastal chic aesthetic without a hint of beach kitsch."Southbound Magazine, winter 2013 (Also,At Home Tennesseecover, 2013) Decorated by Lisa... View all property information
    Location Information
    Seaside, Florida Panhandle
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Hot Tub
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    • Porch
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    • Child-friendly
    • x
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    • x
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    A Sight to Sea - 25 Central Square #305 - Seaside, FL Fall and Winter Special. Rent a minimum of 3 nights and receive an additional night free or book a 1 week stay and get 20% off the weekly rate. Valid 9/5/16-3/10/17 excluding Holidays. “A Sight to Sea” is a sophisticated and stylish two story... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
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    About this property
    'Dreamcatcher' is the original name given to this seaside cottage. The home has a central seaside location on east ruskin street,close to central square and is located less than 6 houses from the beach. The home has two bedrooms and a loft (with two trundle beds), a living area with a cathedral... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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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 required year-round; please no children under the age of 12 with a maximum of two children between the ages of 12-18 This exclusive residence has been the cover story for several publications including Architectural Digest, Coastal Living... View all property information
    Location Information
    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    201 Smolian Circle 3-night minimum stay is required year round; 5-night minimum for spring break and summer Every 'Now and Then,' you discover the perfect place to kick back and relax. This lovely home includes a spacious floor plan and themed bedrooms, each with private bath and perfect for large... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
    1 / 15
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    2132 East County Hwy. 30A 7 night minimum during spring break, summer, Thanksgiving and Christmas holidays; 4 night minimum during spring, fall and winter seasons This lovely 4-bedroom, four-and-a-half bath cottage (formerly known as Ventanas) has an abundance of windows on all levels and in all... View all property information
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    Seaside, Florida Panhandle
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
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    Center Stage – 63 Central Square – Seaside, FL 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 and concerts. Professionally... View all property information
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    Seaside, Florida Panhandle
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    204 Ruskin Place Please no children under the age of 18 Maiden’s Chambre is located on the second floor of Renaissance House in Ruskin Place Artist Colony. It is a lovely one1bedroom unit with an antique Belgian Walnut queen bed and a private full bath with a Whirlpool tub. The inviting living room... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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. This inviting cottage includes a spacious living room with a comfortable dining area, a full bath, and a... View all property information
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    Seaside, Florida Panhandle
    1 / 35
    Studio, Sleeps 25 | Quick View
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    • Hot Tub
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    How about a last minute get-away to the beach? Due to a cancelation, we now have one of our beautiful homes available for August 7-21 and have drastically discounted the rate! It is our brand new 8 bedroom Big Sandy luxury home which can sleep up to 25! Big Sandy is just one block to the beach and... View all property information
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    Seaside, Florida Panhandle
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    3 of 5 stars (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
    • Porch
    • Waterfront
    • Shared Outdoor Pool...
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    • Pet-friendly
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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.... View all property information
    Location Information
    Seaside, Florida Panhandle
    3 of 5 stars Reviewed 25 November 2014
    We chose this unit because of the available dates and the photos posted. We were able to check in earlier than the regular time as the cottage was ready - which we...
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    30 West Ruskin Street 3-night minimum stay required during spring break and summer Moore Fun is conveniently located just a short walk to the beach and Central Square. On the first floor, you will find a living room with a fireplace, dining room, a spacious and fully-equipped kitchen with separate... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Hot Tub
    • Grill
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    Persuasion - 42 Savannah Street – Seaside, FL Fall and Winter Special. Rent a minimum of 3 nights and receive an additional night free or book a 1 week stay and get 20% off the weekly rate. Valid 9/5/16-3/10/17 excluding Holidays. Stay with Sunburst and get up to $280 in Beach Gear delivered to... View all property information
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    Seaside, Florida Panhandle
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2326 East County Hwy. 30A 4 night minimum, spring break and summer 7 night minimum over July 4th and Memorial Day 4 night minimum (Easter, Labor Day, Columbus Day, Veterans Day, Thanksgiving, Christmas and New Year’s) Love Me Tender, Love Me True is located right on Scenic 30A, near Central Square... View all property information
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    Seaside, Florida Panhandle
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    4 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    750 Forest Street Sandy Toes is the combination of Sea Biscuit and Grace Sea, located near the Westside Pool. Sea Biscuit is a Charleston Style Cottage including an outdoor table for 14, a large screened-in porch with dining table for 8, numerous rocking chairs, a sleeping bench, a built-in stereo... View all property information
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    Seaside, Florida Panhandle
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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 Central Square. This stylish cottage has a nice and cozy living room, a dining area and a fully-equipped kitchen... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    16 Natchez Street 5-night minimum stay required during spring break and 7-night minimum in summer Propinquity is located directly across the street from the acclaimed sugar-white-sand beach and emerald-green waters of the Gulf. On the first floor, you will find four bedrooms: one with a king bed... View all property information
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    Seaside, Florida Panhandle
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    652 Forest Street Our Place By the Sea is a lovely, spacious 1-bedroom home with great porches, a nice patio deck, and an observation tower overlooking the Gulf and the town. Beautifully and newly redecorated to warm and lift your spirits, the home welcomes you with a brightly colored front porch... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    20 East Ruskin Street 5-night minimum stay required during spring break and summer PB&J is a newly remodeled home located steps from the beach and Central Square. A large front porch leads you to a vaulted ceiling kitchen, spacious dining area and comfortable sitting area. Down the hall is a king... View all property information
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    Seaside, Florida Panhandle
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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... View all property information
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    Seaside, Florida Panhandle
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    52 East Ruskin Street 3-night minimum stay required during spring break and summer Located just minutes away from the beach, Central Square and the Adult and Family Pools, Blue Suede Shoes is a classic beach cottage for your getaway. With an open furnished porch at the entry, you’ll be able to... View all property information
    Location Information
    Seaside, Florida Panhandle
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • Grill
    • Hot Tub
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    The Bothy - 304 W. Ruskin Place, Seaside, FL New owners Brian and Libby Boyle of St Andrews, Scotland have extensively remodeled The Bothy. Accents of their British heritage are evident throughout the home. This impressive 3 story plus roof deck townhome situated in Ruskin Square has 3 Master... View all property information
    Location Information
    Seaside, Florida Panhandle
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Yes, it's Gulf Front and it's a Beauty at the Beach! This one is Flip Flops and it's spectacular. A beautiful gulf front vacation condo and close to Seaside. In fact, it's located 5 minutes from Seaside Town Center by car. Check the map! Want the beach and not the pricing of Seaside? Flip Flops -... View all property information
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    Seaside, Florida Panhandle
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    55 Central Square 5-night minimum required during spring break and summer; 3-night minimum recommended for remainder of year Beachtime 2 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... View all property information
    Location Information
    Seaside, Florida Panhandle
    1 / 15
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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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... View all property information
    Location Information
    Seaside, Florida Panhandle
    4 of 5 stars Reviewed 16 November 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 three...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Private Outdoor...
    • Balcony
    • Internet Access
    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Unforgettable - 25 Central Square #307 - Seaside, FL Fall and Winter Special. Rent a minimum of 3 nights and receive an additional night free or book a 1 week stay and get 20% off the weekly rate. Valid 9/5/16-3/10/17 excluding Holidays. Unforgettable is a sophisticated and spacious two story... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    2368 East County Hwy. 30A 6-night minimum stay required during summer; 3-night minimum stay required during New Year’s holiday Southern Exposure offers its guests spectacular views of the sugar-white sand beach of Seaside and emerald-green waters of the Gulf of Mexico. The first floor of this... View all property information
    Location Information
    Seaside, Florida Panhandle
    1 / 6
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Bella Vista is an original Seaside cottage, built in 1981 on Tupelo Street. Its quaint beach decor with its oversized screen porch have made it a favorite family destination for many years. Being just the second house on Tupelo puts it only a few steps to the beach pavilion. The cottage sleeps up... View all property information
    Location Information
    Seaside, Florida Panhandle
    5 of 5 stars Reviewed 9 June 2012
    What a wonderful vacation we had in Seaside and the Bella Vista was just perfect for us. We spent a week in this cozy beach house and it had everything we needed and more. It is...
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