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Holiday Rentals with Pools in Seaside

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    Travellers to Seaside are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    25 Matching Rentals in SeasideView all 78 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tuscany – 210 W. Ruskin Place – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Tuscany is a spacious, stately townhome perfectly located in the heart of Ruskin Place Artist Colony. It has 2 bedrooms and 2.5 baths and sleeps up to 7 people. The...
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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bewildered1 / 27
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Balcony
    • Washer
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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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
    • Air Conditioning
    • 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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    West Indian – 23 Odessa Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! This 1 bedroom, 1 bath carriage home is the perfect spot for 1 or 2 guests. Located just 4 homes north of Seaside’s private beaches and minutes to the town center,...
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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tresor de la Mer1 / 32
    (1)Excellent
    1 Bedroom, 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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    • Hot Tub
    • Grill
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    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 2 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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    • 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 3 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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    32459, Seaside, Florida Panhandle
    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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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    32459, Seaside, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Hot Tub
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    Suitability
    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
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    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Barefoot in the Rain
    8 Bedrooms, 10 Bathrooms, Sleeps 26 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
    Suitability
    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 26
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    Sea Sabella1 / 32
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • DVD Player
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    Sea Sabella – 2314 E. County Hwy 30A – Seaside, FL This luxurious three story home has fifty feet of Gulf frontage and features a beautiful and spacious floor plan. Sea Sabella's specially milled sunken cypress siding was reclaimed from some of North Florida's own rivers and makes the house a...
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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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)
    • Grill
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • 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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    About this property
    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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 5 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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    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    32459, Seaside, Florida Panhandle
    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
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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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    32459, Seaside, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Waterfront
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    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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    32459, Seaside, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    32459, Seaside, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beachfront 101 / 29
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Parking
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 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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    32459, Seaside, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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