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Holiday Rentals with Pools in Seaside

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    Travellers to Seaside are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    31 Matching Rentals in SeasideView all 84 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
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    • 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 Exciting Renovations for the 2019 Season. More details to come... Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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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 19 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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    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
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    • 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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Above the Crowd1 / 35
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2018
    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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    Unforgettable1 / 29
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • 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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    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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    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)
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    • 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, Gulf Front in Seaside 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 front...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 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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    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 5 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 17 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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    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
    • Washer
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    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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    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)
    • Air Conditioning
    Suitability
    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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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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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    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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home Highlights: - Private Pool - 5 adult bikes provided - Gulf Views - Large Porches - Convenient Location Location: This home is steps from the beach! Sleeping Arrangements (Sleeps 16): First Floor: - Guest Bedroom: King Bed, Private Bathroom with Shower Only -...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Patio
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful cottage is located south of Scenic Highway 30A in the wonderful neighborhood of Old Florida Cottages. Brick paved pedestrian paths & picket fences serve as a backdrop for tropical landscaping & palm trees lining the quiet streets. This home is across the street from the heated...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    Make plans to spend a relaxing vacation in this cozy cottage located in the family-oriented community. You will be delighted with the adorable decor and colorful decorative touches found in this special cottage. Four porches provide wonderful spots to enjoy the gulf breezes. Beautifully landscaped...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Patio
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    * 3 adult bikes * Private Heated Pool ~ Pool heating is available for this property from October 1st through May 1st for an additional fee of $25 per day. Pool will be heated to 83 degrees and cannot be changed. * Gulf views from the third floor tower * Newly painted interior * TVs in every bedroom...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    7 Bedrooms, 8 Bathrooms, Sleeps 28 Quick View
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    • Private Outdoor Pool (Unheated)
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    • Patio
    • Air Conditioning
    • Hot Tub
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home Highlights: - Resort Private Pool and Spa - Swim-Up Bar - Outdoor Living Area - Gulf Views - 3 Living Rooms - Outdoor Gas Grill - Foosball Table - Indoor/Outdoor Wet Bars - Spacious Porches - Gourmet Kitchen - Dual Master Suites - Pool Cabana with 48' Grill - Dining...
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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 28
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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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    This cozy comfortably furnished South Walton vacation rental has one bedroom and would be a perfect place to go to enjoy a romantic getaway for two. However, it can accommodate up to six for a small family vacation as it comes with bunk beds tucked off the hallway and a queen sized sleeper sofa....
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
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    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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    Seaside, Florida Panhandle 32459
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
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    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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    Location Information
    Seaside, Florida Panhandle 32459
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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