Holiday Homes in Southwest Florida

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Southwest Florida and around

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is €305
includes taxes & fees
10 Oct - 11 Oct
Siesta Heron Suites & Villas

Hibiscus House Bed Breakfast Seashell Room

2.0 star property
The price is €186
includes taxes & fees
21 Oct - 22 Oct
Hibiscus House Bed Breakfast Seashell Room

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!"
The price is €222
includes taxes & fees
10 Oct - 11 Oct
Charming home near Anna Maria Island with Jacuzzi

Historic Studio Carriage House, 15min to Beach

2.0 star property
10.0 out of 10, Exceptional, (10)
"Nice little spot close to downtown Bradenton. "
Historic Studio Carriage House, 15min to Beach

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!"
The price is €376
includes taxes & fees
8 Nov - 9 Nov
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

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. "
The price is €359
includes taxes & fees
14 Oct - 15 Oct
Siesta Key Island Rentals

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

9.6 out of 10, Exceptional, (35)
"This was a calming, relaxing, and refreshing destination. There are unique places to visit nearby."
The price is €201
includes taxes & fees
13 Oct - 14 Oct
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Island Paradise: Steps to Private Gulf Beaches, Pools, Hot Tub & Golf Cart ALL

9.8 out of 10, Exceptional, (30)
"Very relaxing and laid back."
The price is €838
includes taxes & fees
10 Oct - 11 Oct
Island Paradise: Steps to Private Gulf Beaches, Pools, Hot Tub & Golf Cart ALL

Kapok in Bradenton

9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
The price is €416
includes taxes & fees
1 Nov - 2 Nov
Kapok in Bradenton

Peaceful Room 15 Minutes from Downtown or Beach

9.6 out of 10, Exceptional, (25)
"Easy to find and just as listed. Awesome decor and very comfy bed. Owner very accommodating and answered messages and phone calls when I needed her! Drive to beach each day! "
The price is €115
includes taxes & fees
22 Oct - 23 Oct
Peaceful Room 15 Minutes from Downtown or Beach

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

9.6 out of 10, Exceptional, (52)
"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!"
The price is €207
includes taxes & fees
12 Oct - 13 Oct
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Lulu's Key House Kemp Ridley 1/1 Downstairs

3.5 star property
10.0 out of 10, Exceptional, (4)
"Loved the location! "
The price is €427
includes taxes & fees
14 Oct - 15 Oct
Lulu's Key House Kemp Ridley 1/1 Downstairs

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (66)
"The home was decorated beautiful! We enjoyed ourselves. Comfortable and kitchen were stocked nicely. Great location, 5-10 minutes from most places of interest. Nice communication and easy to check in and out. "
The price is €173
includes taxes & fees
13 Oct - 14 Oct
Casa Azul 2Bed/1Bath

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"
The price is €226
includes taxes & fees
10 Oct - 11 Oct
Completely remodeled beautiful waterfront property on canal with dock

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. "
Enjoy a 3-bedroom vacation home in Yacht Club, 19 minutes to Key West Express

Myakka River

9.8 out of 10, Exceptional, (18)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
Myakka River

Bradenton Breeze

4.0 star property
6.0 out of 10, (2)
"It was good! "
The price is €280
includes taxes & fees
22 Oct - 23 Oct
Bradenton Breeze

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. "
The price is €353
includes taxes & fees
23 Oct - 24 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage

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"
The price is €216
includes taxes & fees
12 Oct - 13 Oct
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Tropical Vacation Home Marco Island Florida - Close to Beaches-Pet Friendly-POOL

10.0 out of 10, Exceptional, (45)
"Great place"
The price is €490
includes taxes & fees
12 Oct - 13 Oct
Tropical Vacation Home Marco Island Florida - Close to Beaches-Pet Friendly-POOL
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Florida Hotel Reviews

Find out more about Southwest Florida

Find out more about Southwest Florida

Southwest Florida Holiday Homes information

Number of reviews
Accommodation
Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia