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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Southwest Florida and around

Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen

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

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 €295
includes taxes & fees
23 Aug - 24 Aug
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
September discount,15 mins to AMI, walk to Main St
1 bedroom, iron/ironing board, travel cot, free WiFi

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
The Ultimate Fishing Retreat- Comfortable and Convenient!
Fridge, microwave, oven, stovetop

The Ultimate Fishing Retreat- Comfortable and Convenient!

2.0 star property
9.8 out of 10, Exceptional, (11)
"Great place"
The price is €402
includes taxes & fees
24 Aug - 25 Aug
The Ultimate Fishing Retreat- Comfortable and Convenient!
Hibiscus House Bed Breakfast Inn Flamingo Suite
House

Hibiscus House Bed Breakfast Inn Flamingo Suite

The price is €184
includes taxes & fees
23 Aug - 24 Aug
Hibiscus House Bed Breakfast Inn Flamingo Suite
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
Beach nearby

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 €403
includes taxes & fees
29 Aug - 30 Aug
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Outdoor dining

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
24 Aug - 25 Aug
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Completely remodeled beautiful waterfront property on canal with dock
Property grounds

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 €210
includes taxes & fees
31 Aug - 1 Sept
Completely remodeled beautiful waterfront property on canal with dock
Bradenton Breeze
Deluxe Villa | Living area

Bradenton Breeze

4.0 star property
6.0 out of 10, (2)
"It was good! "
The price is €423
includes taxes & fees
27 Aug - 28 Aug
Bradenton Breeze
NEW!! The “WATERSIDE” COTTAGE~With dockage
Pool

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 €344
includes taxes & fees
25 Aug - 26 Aug
NEW!! The “WATERSIDE” COTTAGE~With dockage
Charming home near Anna Maria Island with Jacuzzi
Smart TV, stereo

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 €241
includes taxes & fees
29 Aug - 30 Aug
Charming home near Anna Maria Island with Jacuzzi
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Beach

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 €380
includes taxes & fees
16 Sept - 17 Sept
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
House, 3 Bedrooms | Property grounds

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

3.0 star property
The price is €373
includes taxes & fees
23 Aug - 24 Aug
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
Outdoor dining

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 €438
includes taxes & fees
30 Aug - 31 Aug
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
Boca Grande Hotel - Queen Room
Exterior

Boca Grande Hotel - Queen Room

8.8 out of 10, Excellent, (12)
"Enjoyed boca grande very much. Hotel was ver clean. Location was great."
The price is €161
includes taxes & fees
24 Aug - 25 Aug
Boca Grande Hotel - Queen Room
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
Outdoor pool, a heated pool

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
2 Bedroom 2 Bath home near Siesta Key Beach
Exterior

2 Bedroom 2 Bath home near Siesta Key Beach

8.4 out of 10, Very good, (28)
"The house was great forour family vacation. The location was close to everything we wanted to do. Would definitely stay here again!"
The price is €193
includes taxes & fees
24 Aug - 25 Aug
2 Bedroom 2 Bath home near Siesta Key Beach
Gulf Coast Retreat: 3BR Canal Front with Pool
Outdoor dining

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."
Gulf Coast Retreat: 3BR Canal Front with Pool
Tiny House Yellow Lifeguard Stand- pet friendly
Interior

Tiny House Yellow Lifeguard Stand- pet friendly

9.6 out of 10, Exceptional, (43)
"We enjoyed the stay and it worked well. "
The price is €170
includes taxes & fees
26 Aug - 27 Aug
Tiny House Yellow Lifeguard Stand- pet friendly
Casa Azul 2Bed/1Bath
Terrace/patio

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
Sign in
Sign up, it's free

Top Southwest Florida Hotel Reviews

Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

10/10 Excellent
"Everything about the property was amazing it exceeded my expectations, food all restaurants on site were great !! comfortable rooms easy access to the beach and three pools. There are a few things that consumer should know it is a cash free establishment. Everything is charged to your room with taxes, gratuity, and fees as well. There is a bus that runs up to Times Square and over the bridge you will need exact change and be aware of the times for pick up and drop off. Or you can use golf cart service for 3 bux.. this place was great 10 out of 10 "
Chelsea Quinn 5-night trip
Posted 11 hours ago
Pink Shell Beach Resort and Marina