Holiday Homes in Southwest Florida

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Our top choices for Southwest Florida holiday homes

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
Noel Real Estate

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
Siesta Heron Suites & Villas

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, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
Nestled in North Port. Updated 2 Bed / 1 Bath.

Tropical Mango Grove Stay Whiskey Creek Area

Tropical Mango Grove Stay Whiskey Creek Area
2.0 star property
McGregor
Tropical Mango Grove Stay Whiskey Creek Area

Kapok in Bradenton

Kapok in Bradenton
Sunny Shores
9.4 out of 10, Exceptional, (40 reviews)
"Excellent for a family trip."
United States
RHEA
Kapok in Bradenton

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, (25 reviews)
"Great little place. Very clean. Convenient location. All the niceties. "
United States
Ryan M.
Charming 2-bedroom house in lovely Sarasota with yard.

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

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.2 out of 10, Wonderful, (77 reviews)
"Great place to stay!"
United States
Wendi B.
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Path to Paradise.

Path to Paradise.
Olde Englewood Village
Path to Paradise.

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, (45 reviews)
"The house was clean and comfortable and the landcaping and outdoor seating was more than perfect! Communications were excellent as well. I highly recommend. We will visit again if the need arises."
United States
CAROLE
Swimming pool, lake view, minutes to Naple's downtown and beach.

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, (62 reviews)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
Completely remodeled beautiful waterfront property on canal with dock

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
East Naples
9.0 out of 10, Wonderful, (22 reviews)
"Great location and perfect spot for my quick work trip "
United States
Anastasia A.
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.

Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.
Kensington Park
9.2 out of 10, Wonderful, (32 reviews)
"Nice place to stay "
United States
Kari O.
Charming 2 bedroom 2 bathroom home with pool in Sarasota with central location.

Lakeside Haven with Heated Pool

Lakeside Haven with Heated Pool
Hancock
9.2 out of 10, Wonderful, (45 reviews)
"Fun great location"
United States
William H.
Lakeside Haven with Heated Pool

Backyard Oasis & Resort Style Pool

Backyard Oasis & Resort Style Pool
Bradenton
10.0 out of 10, Exceptional, (54 reviews)
"The pool area was wonderful at night!"
United States
Jessica S.
Backyard Oasis & Resort Style Pool

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

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
West End
9.2 out of 10, Wonderful, (43 reviews)
"Very responsive host. The cottage was roomy and comfortable and had everything you needed to cook. The bikes were nice and an added bonus. Beach was a couple of hundred yards. Nice neighborhood. We would stay here again. "
United States
Geo K.
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.5 star property
Fort Myers
Bright & Cozy Townhome · Pool & Near Downtown

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

"Manatee" 3 miles to Anna Marie<br>

"Manatee" 3 miles to Anna Marie<br>
Bradenton
9.8 out of 10, Exceptional, (18 reviews)
"Great location and really nice pool. Had a great week here, easy to get to the island and also close to shopping and dining."
United States
Matthew H.
"Manatee" 3 miles to Anna Marie<br>

"Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (32 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
"Stingray" 3 miles to Anna Marie

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

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Pelican
9.4 out of 10, Exceptional, (40 reviews)
"Very clean and loved the space. Very bright and homey. Loved how well equipped the kitchen was since I was there for Thanksgiving and had to cook a little. Not a far drive from some great spots such as Sanibel Island, Bonita Springs and the outlets for some great shopping. Host was great with communication. Would love to stay again next time I’m in the area. "
United States
Stacy D.
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
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.
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Top Southwest Florida Hotel Reviews

Find out more about Southwest Florida

Southwest Florida Holiday Homes information

Number of reviews
495
Accommodation
1051 Holiday Homes
Lowest Price
NZ$312
Highest Price
NZ$964

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