Holiday 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

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

Featured Holiday Homes in Southwest Florida and around

Our top choices for Southwest Florida holiday homes

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

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 €265
includes taxes & fees
27 Aug - 28 Aug
September discount,15 mins to AMI, walk to Main St

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 €137
includes taxes & fees
26 Aug - 27 Aug
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

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 €238
includes taxes & fees
29 Aug - 30 Aug
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, (18)
"Great stay! Nice place and location!"
The price is €293
includes taxes & fees
24 Aug - 25 Aug
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

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"
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, (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 €404
includes taxes & fees
29 Aug - 30 Aug
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

Hibiscus House Bed Breakfast Inn Flamingo Suite

The price is €183
includes taxes & fees
27 Aug - 28 Aug
Hibiscus House Bed Breakfast Inn Flamingo Suite

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...

9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
The price is €434
includes taxes & fees
30 Aug - 31 Aug
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...

Tropical Paradise in Sunny Bonita Springs, Florida

4.0 star property
9.8 out of 10, Exceptional, (9)
"Great location, great house, lots of amenities."
The price is €166
includes taxes & fees
6 Sept - 7 Sept
Tropical Paradise in Sunny Bonita Springs, Florida

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 €252
includes taxes & fees
24 Aug - 25 Aug
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

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 €204
includes taxes & fees
6 Sept - 7 Sept
Off the Charts Inn - Queen Double Room

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 €345
includes taxes & fees
2 Sept - 3 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage

[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 "
[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 €371
includes taxes & fees
3 Sept - 4 Sept
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

9.6 out of 10, Exceptional, (35)
"The unit is very nice with everything for a great comfortable stay.. the water view and onsite restaurants are a bonus "
The price is €184
includes taxes & fees
24 Aug - 25 Aug
RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

Paradise Cove -- A perfect Beach Getaway

10.0 out of 10, Exceptional, (127)
"This property was excellent. It suited all of our needs. Plenty of space and sleeping arrangements. Excellent communication. Excellent location. Kids had a blast in the pool, overall experience was amazing. "
The price is €356
includes taxes & fees
25 Aug - 26 Aug
Paradise Cove -- A perfect Beach Getaway

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 "
The price is €346
includes taxes & fees
25 Aug - 26 Aug
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach

Heated Pool, Strong WI-FI, TV, Tiki Bar & Grill, Boat and Kayak Rentals

8.6 out of 10, Excellent, (9)
"I was looking for a nice place close to the airport and my events, and that's what I found."
Heated Pool, Strong WI-FI, TV, Tiki Bar & Grill, Boat and Kayak Rentals

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (63)
"Very comfortable and perfect location to the airport! "
Casa Azul 2Bed/1Bath
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