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Holiday Rentals in Seaside, FL

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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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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    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
    1 / 15
    4 of 5 stars (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... 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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    1 / 14
    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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    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    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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    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
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    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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    • Shared Outdoor Pool...
    • Porch
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    • Air Conditioning
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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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    1 / 27
    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 / 32
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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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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    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 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, 4 Bathrooms, Sleeps 6 | Quick View
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    123 Grayton Street 5-night minimum stay required during spring break and 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... 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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    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
    • DVD Player
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Beachfront 4-Honeymoon Cottage – 2334 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
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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... 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
    • Waterfront
    • DVD Player
    • Air Conditioning
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    • Washer
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    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
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    Seaside, Florida Panhandle
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Hot Tub
    • Satellite TV
    • Balcony
    • Internet Access
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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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
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    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    12 Butler Street 3-night minimum stay required during spring break and summer; please no children under the age of 8 Travel down a charming footpath, and discover Gimme Shelter, named after a favorite tune of the owners. This stylish cottage is located on Butler Street, which is near the Lyceum and... View all property information
    Location Information
    Seaside, Florida Panhandle
    5 of 5 stars Reviewed 28 April 2016
    I keep thinking of the line, "A clean, well-lighted place." This cottage emanates good vibes. The dramatic two-story windows allow amazing light; I paused a few moments each day...
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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
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    Seaside, Florida Panhandle
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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,... 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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    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 three bedrooms - each with a private bath. The first bedroom has two sets of built-in bunk beds and private... 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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    • Pet-friendly
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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
    1 / 14
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    Seaside, Florida Panhandle
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    758 Forest Street - Seaside, Florida Lion’s Den is located close to the Westside Pool and the Swim & Tennis Club. This cottage is architecturally unique, as well as charming and inviting. The first floor has a bedroom with two twin bunk beds and a private bath, a comfortable living room, dining... 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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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Grill
    • Satellite TV
    • Air Conditioning
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    • Porch
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    Skye – 2026 E. County Hwy 30A – Seaside, FL Beautiful Skye is situated in the quaint town of Seaside, Florida. Located on the beach side with brilliant Gulf views and convenient access to the beach, the home has just undergone an extensive renovation...new chef’s kitchen, new master bathroom,... 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
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    Seaside, Florida Panhandle
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    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Satellite TV
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool...
    • Hot Tub
    • Air Conditioning
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Seaside, Florida Panhandle
    4 of 5 stars Reviewed 16 September 2015
    My husband and I are honeymooning in this house as I write this. It's an adorable little house. Has a king size bed in the downstairs bedroom and a nice bathroom with a large...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
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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... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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 décor and beautiful pickled hardwood floors throughout, Fleur de Lis is a three-bedroom cottage conveniently located near Central Square and... 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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    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, 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. The first floor has a laundry room, as well as a king and queen bedroom- each with a private bath (shower only). The third... 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Private Outdoor...
    • Balcony
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    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
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    Unforgettable - 25 Central Square #307 - Seaside, FL Unforgettable is a sophisticated and 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... 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
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    Seaside, Florida Panhandle
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    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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    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... 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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    54 Robert's Way 3-night minimum stay required during spring break and summer Spinnaker offers plenty of comfort and fun for your family vacation. The first floor has a Master Queen bedroom with a private porch area, as well as a trundle bedroom. Both bedrooms share a hall bath (shower only) that... View all property information
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    Seaside, Florida Panhandle
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2066 East County Hwy. 30A Click here for additional aerial footage Saturday-to-Saturday stay required during summer; 5-night minimum stay required during spring; and 3-night minimum stay required remainder of the year. The Missing Piece is south of 30A, adjacent to the Pensacola Beach Pavilion,... View all property information
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    Seaside, Florida Panhandle
    1 / 35
    Studio, Sleeps 25 | Quick View
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    • Hot Tub
    • Private Outdoor...
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Satellite TV
    • Washer
    • Air Conditioning
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    • x
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    • x
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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 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... View all property information
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    Seaside, Florida Panhandle
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    4.5 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • Satellite TV
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Shared Outdoor Pool...
    • Porch
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    • DVD Player
    • Air Conditioning
    • Balcony
    • Satellite TV
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    • x
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    • x
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    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
    Location Information
    Seaside, Florida Panhandle