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Holiday Rentals with Pools in Seaside

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    Travellers to Seaside are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in SeasideView all 79 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Sea Sabella1 / 32
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Reviewed 1 week ago
    This was our first time to stay on the square in Seaside and we absolutely loved the whole experience. The condo is so pretty and fresh. It was exceptionally clean. The use...
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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 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Life in Shorts– 46 Tupelo Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! If you've ever been to Seaside, you will agree that Life in Shorts is exactly what Seaside stands for and was meant to be.... everything you need for a...
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Balcony
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    Pet friendly
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    Smoking allowed
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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...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    A Sight to Sea - 25 Central Square #305 - Seaside, FL “A Sight to Sea” is a sophisticated and stylish 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 overlooks...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Siena – 210 W. Ruskin Place – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Siena is a second floor cozy one-room efficiency unit in Ruskin Place Artist Colony. There is a queen bed and bath (shower only) and a cozy kitchenette for your...
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Internet Access
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    • Cable/satellite TV
    • Waterfront
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachfront 4- Gulfview Honey Moon 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...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    • Cable/satellite TV
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Caribbean - 23 Odessa Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Colorful décor and artwork adorns this fun coastal cottage! As the name implies, Caribbean is a vibrant beach retreat! Located just steps to the private Odessa beach...
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Unforgettable1 / 29
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Internet Access
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2018
    Unforgettable is in a great location if you want to be right in the heart of all the action in Seaside. I will say that it is well decorated and provides great attention to...
    Reviewed 2 June 2017
    Unforgettable is a perfect, comfortable and beautiful rental. Centrally located where you can park your car and forget about it, except for the required trip to Red Bar. The...
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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...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Belle - Formerly Skye – 2026 E. County Hwy 30A – Seaside, FL Beautiful Belle 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...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Bewildered1 / 28
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    Wonderful place to stay..very close to the beach, shopping and restaurants. Don't miss sunset at Bud & Alley's.
    Reviewed 11 March 2017
    Great place to stay in Seaside, FL! My wife, myself, and two others stayed there while in Seaside for the half marathon. Bewildered was clean and neatly kept. Full kitchen with...
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    Bewildered - 25 Central Square #306 - Seaside, FL Bewildered is a spacious two story penthouse apartment that offers the best of new urbanism living. Located on the third and fourth floor of the 25 Central Square Building in the heart of Seaside, this unit offers panoramic Gulf views that can be...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Forsythe House – 208 W. Ruskin Place – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Located right on Ruskin Park, The Forsythe House is a 3BR/2.5BA townhome that combines both modern and traditional the while maintaining the most unique...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bothy 31 / 43
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
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    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2017
    The decor is clean and modern with a beautiful kitchen. All of the bedrooms and/or sleeping accommodations are .comfortable and well thought out. The bottom apartment is...
    Reviewed 3 May 2017
    Very high specification townhouse within 5 minutes walk to the beach and attractions in Seaside. I was there to take advantage of the Golf on the Gulf Coast and The Bothy was a...
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    The Bothy - 304 W. Ruskin Place, Seaside, FL Rent as Bothy 1 or 2 or 3! Recently remodeled, this impressive 3 story plus roof deck town home situated in Ruskin Square has 3 Master en-suite bedrooms with King beds, a bunk room, Queen Murphy bed and Queen sleeper sofa for a total of 4 bedrooms, 5...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Grill
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    As Luck Would Have It – 123 Quincy Circle – Seaside, FL “As Luck Would Have It” is a sophisticated 4-story townhome situated in Ruskin Place Park in the heart of Seaside, Florida. With two bedrooms and two and one half baths, this elegant art-filled home sleeps six. Multiple porches overlook the...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tresor de la Mer1 / 31
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2017
    Loved everything about our stay. The condo was clean, cute, and convenient! Ideal location in the heart of Seaside where we could walk or bike to beach (yes it is only 75 steps...
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    Tresor de la Mer – 25 Central Square #304 – Seaside, FL Exciting 2018 renovation – all new kitchen and interior finishes plus addition of a bedroom with a Twin bunk bed and an additional bathroom! Tresor de la Mer is a sophisticated and spacious two-story penthouse apartment that offers the best...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gift by the Sea - Gulf front Honeymoon Cottage1 / 25
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2018
    Very comfortable, outstanding location, very nicely appointed.Could use a brighter light over the front door, can,t read the lock numbers without a flashlight.Bob Weber
    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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    Gift by the Sea-Beachfront 9 – 2088 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferson as he built Monticello. These...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Lido Deck – 25 Central Square #303 – Seaside, FL Overlooking Seaside’s Town Center and newly renovated amphitheater, this professionally designed 2-bedroom, 2.5 bath condo offers panoramic gulf views, a beautiful courtyard and two private exterior spaces- all within walking distance to Seaside’s...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
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    Pet 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...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Barefoot in the Rain
    8 Bedrooms, 10 Bathrooms, Sleeps 26 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New home under construction ready for summer 2018 Very upscale home with outdoor lanai with large Viking grill and TV Whole house audio system Elevator Rooftop deck with fabulous gulf views Plans available upon request Professionally decorated by Destiny Designs See other homes on our site...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 26
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE BOTHY 1 - 304 W. RUSKIN PLACE, SEASIDE, FL Seaside Cottage meets Urban European 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. In the off season, you can rent a portion of...
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the New and Upcoming Neighborhood of Highland Park! This charming beach cottage is the located in one of Scenic Hwy 30A’s newest subdivisions, Highland Park. This home has 3 bedrooms and 2.5 bathrooms with plenty of living space for you and your guests. Highland Park is a lovely...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beachfront 101 / 29
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Beachfront 10-Honeymoon Cottage – 2070 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferson as he built Monticello....
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE BOTHY 2 - 304 W. RUSKIN PLACE, SEASIDE, FL For more information or to book your next getaway give us a call at (toll free) *******-5718 Seaside Cottage meets Urban European New owners Brian and Libby Boyle of St Andrews, Scotland have extensively remodeled The Bothy. Accents of their British...
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    Location Information
    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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