Search Vacation Homes in Southwest Florida

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Southwest Florida

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!!"
Siesta Heron Suites & Villas

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"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 ¥23,056
¥48,112 total
includes taxes & fees
Sep 3 - Sep 4
Siesta Key Island Rentals

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 ¥16,927
¥39,698 total
includes taxes & fees
Aug 29 - Aug 30
Charming home near Anna Maria Island with Jacuzzi

#D Seatuit/Boat/Swin/Kayak/Fish/Vacay #D

9.8 out of 10, Exceptional, (29)
"We stayed for spring break to escape the cold! Was a very nice time! The pool was so close it was great! The kitchen had everything we needed. Overall a great stay. "
The price is ¥10,436
¥40,441 total
includes taxes & fees
Aug 27 - Aug 28
#D Seatuit/Boat/Swin/Kayak/Fish/Vacay #D

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

9.4 out of 10, Exceptional, (46)
"The atmosphere and art very local"
The price is ¥17,853
¥22,846 total
includes taxes & fees
Aug 26 - Aug 27
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

September discount,15 mins to AMI, walk to Main St

2.0 star property
10.0 out of 10, Exceptional, (10)
"Nice little spot close to downtown Bradenton. "
The price is ¥14,547
¥44,239 total
includes taxes & fees
Aug 27 - Aug 28
September discount,15 mins to AMI, walk to Main St

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 ¥9,551
¥35,089 total
includes taxes & fees
Aug 31 - Sep 1
Completely remodeled beautiful waterfront property on canal with dock

The Ultimate Fishing Retreat- Comfortable and Convenient!

2.0 star property
9.8 out of 10, Exceptional, (11)
"Great place"
The price is ¥26,596
¥68,380 total
includes taxes & fees
Aug 26 - Aug 27
The Ultimate Fishing Retreat- Comfortable and Convenient!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

2.0 star property
10.0 out of 10, Exceptional, (18)
"Great stay! Nice place and location!"
The price is ¥17,853
¥50,077 total
includes taxes & fees
Aug 26 - Aug 27
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

9.2 out of 10, Wonderful, (37)
"This cottage was clean, convenient and comfortable for all of us! We loved being able to walk to the beach without driving and we also enjoyed the grill!"
The price is ¥29,241
¥67,150 total
includes taxes & fees
Aug 29 - Aug 30
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

Hibiscus House Bed Breakfast Inn Flamingo Suite

The price is ¥29,855
¥33,288 total
includes taxes & fees
Sep 25 - Sep 26
Hibiscus House Bed Breakfast Inn Flamingo Suite

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

9.6 out of 10, Exceptional, (51)
"Love the two beds, two baths!"
The price is ¥15,076
¥36,867 total
includes taxes & fees
Aug 26 - Aug 27
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

9.6 out of 10, Exceptional, (35)
"Looking forward to staying there again."
The price is ¥16,163
¥65,461 total
includes taxes & fees
Aug 26 - Aug 27
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

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 ¥27,919
¥57,488 total
includes taxes & fees
Aug 26 - Aug 27
NEW!! The “WATERSIDE” COTTAGE~With dockage

Off the Charts Inn - Queen Double Room

10.0 out of 10, Exceptional, (2)
"Everything was very nice, clean, quiet, and the people on the Island as very friendly . We loved our stay."
The price is ¥22,467
¥33,721 total
includes taxes & fees
Aug 26 - Aug 27
Off the Charts Inn - Queen Double Room

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

9.6 out of 10, Exceptional, (32)
"We enjoyed our stay. Close to the beach. enjoyed the pool.Kitchen was perfect we were able to make breakfast and dinner."
The price is ¥18,955
¥41,678 total
includes taxes & fees
Aug 26 - Aug 27
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

[lounge like locals] walk to siesta beach +bikes

9.8 out of 10, Exceptional, (23)
"Lovely stay at Siesta Key! Minute walk to beaches and restaurants. Very spacious and clean! Highly recommended "
The price is ¥9,989
¥39,665 total
includes taxes & fees
Aug 26 - Aug 27
[lounge like locals] walk to siesta beach +bikes

Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

3.0 star property
The price is ¥22,000
¥63,919 total
includes taxes & fees
Aug 26 - Aug 27
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach

10.0 out of 10, Exceptional, (162)
"A wonderful home to stay in!! We were more than happy with all.the amennities, and the host was very attentive and we had a great stay. ***** five star location "
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach

Gulf Coast Retreat: 3BR Canal Front with Pool

2.0 star property
10.0 out of 10, Exceptional, (24)
"Gulf coast retreat was a perfect home away from home! The location was fantastic. The space itself was clean, comfortable, and exactly as described in the listing. I especially appreciate the clean heated pool, the well-stocked kitchen, the comfortable bed, etc. The host was responsive and easy to communicate with, making check-in and check-out a breeze. I would definitely recommend this place to anyone looking for a relaxing and enjoyable stay in Cape coral."
The price is ¥10,580
¥60,866 total
includes taxes & fees
Sep 15 - Sep 16
Gulf Coast Retreat: 3BR Canal Front with 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 Vacation Homes information

Number of reviews
1,463
Accommodation
975 Vacation Homes
Lowest Price
¥22,041
Highest Price
¥59,511

Explore a world of travel with Expedia

Explore a world of travel with Expedia