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Seaside Rentals with Pools

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    Travelers to Seaside are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    37 Matching Rentals in SeasideView all 112 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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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Margarita Days1 / 21
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Reviewed November 2, 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...
    Reviewed July 16, 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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    About this property
    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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bothy 31 / 42
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Reviewed May 20, 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 May 2, 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 We are offering 20% off full week stays this summer or less than 7 night stays (as few as 4) for remaining open dates in July and August. Rent as Bothy 1 or 2 or 3! Owners Brian and Libby Boyle of St Andrews, Scotland have extensively remodeled The...
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    Seaside, Florida Panhandle 32459
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Coasting in Style1 / 29
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Terrace
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    • DVD Player
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    • Balcony
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 18, 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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    Coasting in Style – 25 Central Square #304 – Seaside, FL Special pricing for open summer weeks! Four-night minimum! Coasting in Style 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...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    A Sight to Sea - 25 Central Square #305 - Seaside, FL Special pricing for open July weeks! Four night minimum! New for 2017 season, the penthouse has been completely redecorated, painted and floors refinished! “A Sight to Sea” is a sophisticated and stylish two story penthouse apartment that...
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    Seaside, Florida Panhandle
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Forsythe House – 208 W. Ruskin Place – Seaside, FL End of Summer Special - 20% Off! 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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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)
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    • Waterfront
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 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 June 4, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bewildered1 / 27
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 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 End of Summer Special - 20% Off! 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...
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    Seaside, Florida Panhandle
    Rental Home - 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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    Skye – 2026 E. County Hwy 30A – Seaside, FL End of Summer Special - 20% Off! 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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Gift by the Sea - Gulf front Honeymoon Cottage1 / 24
    (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 (Unheated)
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 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 End of Summer Special - 20% Off! 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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Bella Vista1 / 44
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 9, 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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    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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Unforgettable1 / 28
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Balcony
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 2, 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...
    Reviewed May 24, 2017
    This is our fifth year to be in the Seaside area for spring break. Three of the five we have rented through Sunburst Beach Vacations and always have been pleased with their...
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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
    Rental Home - 2 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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    Pet friendly
    Kid friendly
    Smoking allowed
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    As Luck Would Have It – 123 Quincy Circle – Seaside, FL Special pricing for open summer weeks! Four-night minimum! “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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront 101 / 27
    (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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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 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 End of Summer Special - 20% Off! 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...
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachfront 4-Honeymoon Cottage – 2334 E. County Hwy 30A – Seaside, FL Special pricing for open summer weeks! Four-night minimum! 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...
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    Seaside, Florida Panhandle
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
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    • Terrace
    • Balcony
    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Seaside, Florida Panhandle 32459
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Seaside, Florida Panhandle 32459
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Hot Tub
    • Washer
    • Satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Seaside, Florida Panhandle 32459
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Seaside Flight and Weather Info
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    83° 70°
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    84° 70°
    August
    81° 66°
    September
    73° 58°
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