50 Best Seaside Vacation rentals on Holiday Lettings - Beach rentals

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78 Vacation rentals

27

Seaside Vacation home accommodation

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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. Mu …see more

from $336 / night

$2155 - $4525 / week

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from $336 / night

27

Seaside Vacation home rental

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Persuasion - 42 Savannah Street – Seaside, FL 20% OFF weeks of March 25-April 1, April 8-15 and April 15-22, 2017. Please note that this special applies only to new bookings. Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Beauti …see more

from $326 / night

$2103 - $4365 / week

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from $326 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
55 Central Square 4-night minimum required during summer; 3 night minimum remainder of year Alta Vista is conveniently located in the center of town and is stunning from wall to wall. This recently renovated townhouse includes an oversized master bedroom that is elegant …see more

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33

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 kitch …see more

from $736 / night

$4345 - $9313 / week

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from $736 / night

(1) Excellent 

29

Vacation home rental

Florida Panhandle / Seaside

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Coasting in Style – 25 Central Square #304 – Seaside, FL 20% OFF weeks of March 25-April 1, April 8-15 and April 15-22, 2017. Please note that this special applies only to new bookings. Coasting in Style is a sophisticated and spacious two story penthouse apartment t …see more

from $210 / night

$1350 - $2934 / week

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from $210 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
47 Western Lake (Watercolor) 5-night minimum stay required during spring break and summer Located across from the beach, Masterpiece is an expertly decorated home with custom fabrics, original artwork, state-of-the-art appliances and beautiful dark wood floors. The firs …see more

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15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
"Great house, town, beach, food. This house was a very nice place to say." --Starry Night Guest Survey, 2017 13 Odessa Street 5-night minimum stay required during spring break and summer This spectacular cottage is located directly across the street from the beach. The …see more

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15

Seaside Vacation home rental

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
"We loved the house and location. I've stayed in several homes in the area and this was definitely a favorite. Thanks for the beach bag and all the goodies!" --Guest Survey, 2017 52 East Ruskin Street 3-night minimum stay required during spring break and summer Located …see more

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30

Seaside Vacation home rental

Florida Panhandle / Seaside

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 c …see more

from $511 / night

$3030 - $6456 / week

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from $511 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
"Lovely cottage. It was perfect for us! We didn't realize we would have maid service - they were friendly and did a good job. We had a great time." --Southern Exposure Guest Survey, 2017 2368 East County Hwy. 30A 6-night minimum stay required during summer; 3-night mini …see more

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15

Home rental in Seaside

Florida Panhandle / Seaside

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
842 Forest St. 5 night minimum stay required during spring and summer Named after the owners' favorite Jimmy Buffet song, Banana Republic is a 3 BR, 2.5 bath stylish combination of tropical and mid-century décor that sleeps 7 and is located near the Westside community p …see more

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(2) Excellent 

33

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 rive …see more

from $1051 / night

$6180 - $13380 / week

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from $1051 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
54 Robert's Way 3-night minimum stay required during spring break and summer Spinnaker offers plenty of comfort and fun for your family vacation and is just 4 houses from 30A and the beach. It has been completely renovated in 2017, and you will delight in the updated fu …see more

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15

Vacation home rental

Florida Panhandle / Seaside

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
2132 East County Hwy. 30A 7-night minimum during spring break & summer; 4-night minimum duringThanksgiving and Christmas holidays,spring, fall and winter seasons This lovely 4-bedroom, four-and-a-half bath cottage has an abundance of windows on all levels and in all dir …see more

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(1) Very Good 

15

Vacation home rental

Florida Panhandle / Seaside

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
31 Smolian Circle Saturday-Saturday stay required during summer; 3-night minimum stay required remainder of the year Your train has finally pulled into "The Station" when you spend your Seaside, FL vacation in this cottage. Located just minutes from the Westside pool, t …see more

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15

Vacation home in Seaside

Florida Panhandle / Seaside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
751 Forest Street 5-night minimum stay required during spring and summer Comfort, class, and conveniences- Southern Splendor offers it all. The front entry leads you into a fully-equipped kitchen with a gas stove and bar seating, as well as a living area, a dining area …see more

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15

Vacation home rental

Florida Panhandle / Seaside

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Ask about children
119 Quincy Circle 4-night minimum stay required during spring break and summer PET FRIENDLY As one of the only dog-friendly rentals in Seaside, Cherished View is the combination of the townhouse, Cherished by the Sea, and the penthouse, Room with a View. With its prime …see more

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15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
2454 East County Hwy. 30A Please no children under the age of 5; 5-night minimum stay required during spring break and summer A lovely, colorful home with lots of windows to enjoy the Gulf and Seaside views, not to mention porches and patios on every level, Toye Cottage …see more

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11

Condo rental in Seaside

Florida Panhandle / Seaside

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
Ideally located in the heart of Seaside's Ruskin Place, STAIRWAY TO HEAVEN is the consummate new urban residence. Widely admired and internationally published, this three story residence is a child of the Bauhaus International Modern Movement. Cast in the 1996 movie, ' …see more

from $775 / night

$5425 / week

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from $775 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
73 Odessa Street 5-night minimum during spring break and summer Settle right in to Furs, Fins and Feathers and take advantage of the porch swings, sun deck and its nearby location to Westside Pool and the Gulf. This classic Seaside beach cottage includes a dine-in kitch …see more

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13

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
"Very comfortable cottage. Love the tower room on top!" --O Happy Day Guest Survey, 2017 61 Savannah Street 5-night minimum stay required during spring break and summer O Happy Day is a charming cottage that will have you feeling happy all day long. Enter and find a whi …see more

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(1) Very Good 

27

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Bewildered - 25 Central Square #306 - Seaside, FL 20% OFF weeks of March 25-April 1, April 8-15 and April 15-22, 2017. Please note that this special applies only to new bookings. Bewildered is a spacious two story penthouse apartment that offers the best of new urban …see more

from $255 / night

$1650 - $3588 / week

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from $255 / night

14

Home rental in Seaside

Florida Panhandle / Seaside

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
"It was wonderful! The house worked so well for our group of twelve. It was very clean, and we enjoyed ourselves very much." --Guest Survey, 2017 142 East Ruskin Street Located near the pools, fitness center and tennis courts, Big Pink is also just a short walk to Ruski …see more

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11

Vacation home in Seaside

Florida Panhandle / Seaside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
"The cottage was absolutely wonderful and had everything needed! Was perfect for large group, especially the 2nd floor den. The house was great and Seaside itself just keeps getting better and better!" --Guest Survey, 2017 20 East Ruskin Street 5-night minimum stay requ …see more

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14

Vacation home in Seaside

Florida Panhandle / Seaside

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
2120 East County Hwy. 30A Limited Saturday-to-Saturday stay during peak summer season; please no children under the age of 3 This exclusive residence has been the cover story for several publications including Architectural Digest, Coastal Living, The Coastal Cottage, 3 …see more

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15

Seaside Vacation home rental

Florida Panhandle / Seaside

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Ask about children
750 Forest Street 5-night minimum spring break and summer Sandy Toes is the combination of Sea Biscuit and Grace Sea, located near the Westside Pool. This popular Seaside rental has recently been renovated with new paint and furnishings for a fresh, relaxed beach home a …see more

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(2) Excellent 

42

Vacation home rental

Florida Panhandle / Seaside

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
The Bothy - 304 W. Ruskin Place, Seaside, FL We have reduced our summer rates 5%! 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. This impressive 3 story …see more

from $586 / night

$3760 - $8056 / week

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from $586 / night

11

Home rental in Seaside

Florida Panhandle / Seaside

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
210 Ruskin Place 3-night minimum stay required during spring break and summer Tuscany is a spacious, stately townhome perfectly located in the heart of Ruskin Place Artist Colony. The second floor includes a fully-equipped kitchen with granite counter tops, bar seating …see more

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(1)  

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
45 Central Square 5-night minimum stay required during spring break and summer Far Niente is short for “doing nothing” and this is the perfect place for doing exactly that! This grand two-story penthouse is located above Central Square in Seaside, offering panoramic vie …see more

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24

Vacation home accommodation

Florida Panhandle / Seaside

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Beachfront 4-Honeymoon Cottage – 2334 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferso …see more

from $356 / night

$2125 - $4465 / week

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from $356 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
764 Forest Street 5-night minimum stay required during spring break and summer;Saturday to Saturday required during July 4th holiday week Located near the Westside Pool, the beach and Central Square, Mojo Biblio is a unique home with an open, airy and spacious floor pla …see more

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34

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
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 bath …see more

from $280 / night

$1785 - $3885 / week

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from $280 / night

14

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
19 Rosewalk 3-night minimum stay required during spring break and summer Mis B’Haven is tucked away in Rosewalk, a cluster of quaint cottages with a pedestrian footpath meandering through a thick grove of oaks trees. This cozy and charming cottage features tongue and gr …see more

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15

Seaside Vacation home rental

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
30 West Ruskin Street 3-night minimum stay required during spring break and summer Moore Fun is conveniently located just a short walk to the beach and Central Square. On the first floor, you will find a living room with a fireplace, dining room, a spacious and fully-eq …see more

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14

Vacation home rental

Florida Panhandle / Seaside

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
32 Pensacola Street Please no children under that age of 9 Takin It E-sea, located down a short footpath, is the guest house for the main cottage Shore is Fun. Ideally situated, you are just a short stroll from the acclaimed white-sand beach and emerald-green waters of …see more

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15

Home rental in Seaside

Florida Panhandle / Seaside

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
"We enjoyed this home so much. It was so clean and well kept, we loved the atmosphere and everything being so close by. Thank you for sharing your home!" --Our Place Guest Survey, 2017 652 Forest Street Our Place By the Sea is a lovely, spacious 1-bedroom home with grea …see more

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15

Vacation home in Seaside

Florida Panhandle / Seaside

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
"We had an awesome experience. We stayed in this same cottage many, many years ago and very pleased to see the updates the owners had made. Nicely done!" --Moon Shine Guest Survey, 2017 62 Pensacola Street 5-night minimum stay required during summer Moon Shine is a grea …see more

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15

Vacation home in Seaside

Florida Panhandle / Seaside

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
"The cottage was in a great location and is a really nice place to be." --Whatcha Dune Guest Survey, 2017 608 Forest Street 5-night minimum stay required during spring break and summer Whatcha Dune is family-friendly cottage located near the Seaside Chapel, directly acr …see more

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14

Seaside Vacation home rental

Florida Panhandle / Seaside

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Ask about children
147 Grayton Street The Old Natchez Compound is conveniently located across from the Westside Pool and combines three separate living areas- perfect for a large family or group. On the left side of the compound, Oak Creek Annie’s (OAKCR) speaks of rustic times and folklo …see more

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15

Vacation home in Seaside

Florida Panhandle / Seaside

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
2326 East County Hwy. 30A Love Me Tender, Love Me True is located right on Scenic 30A, near Central Square and just 32 steps to the East Ruskin Beach Pavilion, one of Seaside's most photogenic beach walk-overs. Complete with beautiful fixtures, upper-level vaulted ceili …see more

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