Search Vacation Homes in Southwest Florida

  • 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

In two weeks
In two months
In three months
In four months

Our top choices for Southwest Florida vacation homes

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is ¥24,269
¥61,450 total
includes taxes & fees
Jun 17 - Jun 18
Siesta Key Island Rentals

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (43 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ¥18,501
¥53,199 total
includes taxes & fees
Jun 16 - Jun 17
Siesta Heron Suites & Villas

Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.4 out of 10, Exceptional, (3 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
The price is ¥22,192
¥69,147 total
includes taxes & fees
Jun 23 - Jun 24
Noel Real Estate

Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (65 reviews)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
The price is ¥10,427
¥37,665 total
includes taxes & fees
Jun 18 - Jun 19
Completely remodeled beautiful waterfront property on canal with dock

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is ¥13,813
¥35,271 total
includes taxes & fees
Jun 12 - Jun 13
Nestled in North Port. Updated 2 Bed / 1 Bath.

Swimming pool, lake view, minutes to Naple's downtown and beach.

Swimming pool, lake view, minutes to Naple's downtown and beach.
East Naples
9.2 out of 10, Wonderful, (47 reviews)
"Simply a wonderful stay. The pool was a plus."
United States
Toni G.
The price is ¥24,062
¥30,077 total
includes taxes & fees
Jun 16 - Jun 17
Swimming pool, lake view, minutes to Naple's downtown and beach.

Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (10 reviews)
"This was our second stay at Driftwood Inn and we enjoyed it as much this time as the last! Property is immaculately cleaned, comfortable and has everything we need. The beach is a short walk away and the included cart, umbrellas and beach chairs make it easy to enjoy your time relaxing in the sun. Highly recommend this property for your beach time!"
United States
Heather
The price is ¥48,623
¥92,686 total
includes taxes & fees
Jun 17 - Jun 18
Driftwood Inn

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.4 out of 10, Exceptional, (79 reviews)
"It was very clean, appreciated that. "
United States
Juanita D.
The price is ¥17,757
¥29,618 total
includes taxes & fees
Jun 17 - Jun 18
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home

Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home
3.0 star property
Hancock
The price is ¥18,400
¥83,780 total
includes taxes & fees
Jun 12 - Jun 13
Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home

Tropical Mango Grove Stay Whiskey Creek Area

Tropical Mango Grove Stay Whiskey Creek Area
2.0 star property
McGregor
The price is ¥17,293
¥47,327 total
includes taxes & fees
Jun 16 - Jun 17
Tropical Mango Grove Stay Whiskey Creek Area

Emerald Entry Retreat

Emerald Entry Retreat
2.0 star property
LaBelle
The price is ¥27,437
¥66,655 total
includes taxes & fees
Jun 24 - Jun 25
Emerald Entry Retreat

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is ¥20,374
¥53,879 total
includes taxes & fees
Jun 23 - Jun 24
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (141 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is ¥15,894
¥80,478 total
includes taxes & fees
Jun 15 - Jun 16
IMG Lake & Beach Home with Pool White Sand Beaches MAY 16-10, Oct, Nov SPECIALS!

Kapok in Bradenton

Kapok in Bradenton
Sunny Shores
9.6 out of 10, Exceptional, (41 reviews)
"The property exceptionally clean."
United States
David R.
The price is ¥20,051
¥85,086 total
includes taxes & fees
Jun 30 - Jul 1
Kapok in Bradenton

Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean and well accommodating. There was room for our boat in the driveway. Will definitely stay again if in the area."
United States
Jeremy
The price is ¥14,305
¥45,314 total
includes taxes & fees
Jun 22 - Jun 23
Path to Paradise.

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.5 star property
Fort Myers
The price is ¥28,874
¥57,234 total
includes taxes & fees
Jun 12 - Jun 13
Bright & Cozy Townhome · Pool & Near Downtown

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (38 reviews)
"We had a very comfortable stay and had all the amenities that we needed."
United States
Susan H.
Mimosa Memories

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.0 out of 10, Wonderful, (28 reviews)
"Easy check in . Clear communication.Beautiful home .Quiet neighborhood ! No surprises. Highly recommend."
United States
Paula
Charming 2-bedroom house in lovely Sarasota with yard.

Home in quiet Bird Sanctuary Neighborhood, close to Beach

Home in quiet Bird Sanctuary Neighborhood, close to Beach
South Venice
9.6 out of 10, Exceptional, (19 reviews)
"Good location for us"
United States
EdgefieldFarm
The price is ¥14,437
¥49,968 total
includes taxes & fees
Jun 23 - Jun 24
Home in quiet Bird Sanctuary Neighborhood, close to Beach

Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is ¥21,896
¥45,115 total
includes taxes & fees
Jul 1 - Jul 2
Lakeview Bradenton Rental Near Beaches & IMG
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

Southwest Florida Vacation Homes information

Number of reviews
389
Accommodation
1109 Vacation Homes
Lowest Price
¥29,618
Highest Price
¥92,686

Explore a world of travel with Expedia