Holiday Homes in Southwest Florida

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Featured Holiday Homes in Southwest Florida

Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$839
includes taxes & fees
24 Oct - 25 Oct
Siesta Heron Suites & Villas
Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
United States
Julianna
The price is AU$414
includes taxes & fees
26 Oct - 27 Oct
Siesta Key Island Rentals
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
9.6 out of 10, Exceptional, (36)
"This was a calming, relaxing, and refreshing destination. There are unique places to visit nearby."
United States
Donna R.
The price is AU$354
includes taxes & fees
26 Oct - 27 Oct
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Charming home near Anna Maria Island with Jacuzzi
2.0 star property
10.0 out of 10, Exceptional, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
United States
Kyle S.
The price is AU$438
includes taxes & fees
26 Oct - 27 Oct
Charming home near Anna Maria Island with Jacuzzi
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
2.0 star property
10.0 out of 10, Exceptional, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is AU$547
includes taxes & fees
24 Oct - 25 Oct
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Hibiscus House Bed Breakfast Citrus Room
2.0 star property
The price is AU$339
includes taxes & fees
27 Oct - 28 Oct
Hibiscus House Bed Breakfast Citrus Room
Historic Carriage House, 15 min to AMI Beach & IMG
2.0 star property
10.0 out of 10, Exceptional, (10)
"Nice little spot close to downtown Bradenton. "
United States
Matt
The price is AU$373
includes taxes & fees
28 Oct - 29 Oct
Historic Carriage House, 15 min to AMI Beach & IMG
Enjoy a 3-bedroom vacation home in Yacht Club, 19 minutes to Key West Express
9.8 out of 10, Exceptional, (118)
"My husband and I had a very relaxing 10 days here. Very quiet neighborhood and close enough to ride the bikes to Cape Coral beach. "
United States
Leigh L.
The price is AU$602
includes taxes & fees
24 Oct - 25 Oct
Enjoy a 3-bedroom vacation home in Yacht Club, 19 minutes to Key West Express
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
9.6 out of 10, Exceptional, (53)
"Reasonably priced for our getaway. Located close enough for a short drive to the beach for us. The place was very clean. I would stay again!"
United States
Rachel B.
The price is AU$362
includes taxes & fees
26 Oct - 27 Oct
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Kapok in Bradenton
9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
United States
RHEA
The price is AU$737
includes taxes & fees
18 Nov - 19 Nov
Kapok in Bradenton
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
10.0 out of 10, Exceptional, (55)
"We enjoyed the close proximity to the beaches. Great stay would love to come back!"
United States
Scott L.
The price is AU$513
includes taxes & fees
24 Oct - 25 Oct
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
Perfect Getaway with the pool
10.0 out of 10, Exceptional, (26)
"We enjoyed our stay very much. Will stay again"
United States
Christi K.
The price is AU$599
includes taxes & fees
27 Oct - 28 Oct
Perfect Getaway with the pool
[lounge like locals] walk to siesta beach +bikes
9.8 out of 10, Exceptional, (24)
"The property was very clean and conveniently located ."
United States
David
The price is AU$483
includes taxes & fees
24 Oct - 25 Oct
[lounge like locals] walk to siesta beach +bikes
Completely remodeled beautiful waterfront property on canal with dock
9.6 out of 10, Exceptional, (61)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
The price is AU$401
includes taxes & fees
24 Oct - 25 Oct
Completely remodeled beautiful waterfront property on canal with dock
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
9.2 out of 10, Wonderful, (38)
"We enjoyed our stay. Great beach supplies were available."
United States
Anonymous traveller
The price is AU$723
includes taxes & fees
24 Oct - 25 Oct
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
10.0 out of 10, Exceptional, (65)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
The price is AU$390
includes taxes & fees
28 Oct - 29 Oct
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Stylish house minutes from the beach
9.6 out of 10, Exceptional, (25)
"Great location and safe neighborhood. Definitely will stay again if available."
United States
Luis M.
Stylish house minutes from the beach
NEW!! The “WATERSIDE” COTTAGE~With dockage
10.0 out of 10, Exceptional, (41)
"My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly. "
United States
Ron R.
The price is AU$609
includes taxes & fees
27 Oct - 28 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage
Waterfront Getaway, a Boating Paradise
10.0 out of 10, Exceptional, (43)
"Great place to stay with your boat."
United States
arthur n.
The price is AU$535
includes taxes & fees
1 Nov - 2 Nov
Waterfront Getaway, a Boating Paradise
The BEACH & BAY 120 steps away. Semi-private fishing dock, free bikes
9.8 out of 10, Exceptional, (113)
"This was our second time at this location and fourth year at one of Dan & Linda’s properties. Everything was clean and to be expected! We had just enough amenities and perfect access to our local favorites (beach, walking paths, restaurants). Manasota Key is a hidden gem and we’re eager to see it back on its feet from last year’s storms. Grateful for an amazing stay. "
United States
Elizabeth J.
The price is AU$642
includes taxes & fees
25 Oct - 26 Oct
The BEACH & BAY 120 steps away. Semi-private fishing dock, free bikes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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