Holiday Homes in Southwest Florida

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Check prices for these dates

Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov
In one month
28 Nov - 30 Nov
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26 Dec - 28 Dec

Featured Holiday Homes in Southwest Florida and around

322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen
Siesta Key Island Rentals
Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (48)
"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. "
United States
Julianna
The price is €252
includes taxes & fees
30 Oct - 31 Oct
Siesta Key Island Rentals
Condo, Pool View | Private kitchen
Siesta Heron Suites & Villas
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
Siesta Heron Suites & Villas
Sun-loungers, beach towels
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.
9.6 out of 10, Exceptional, (36)
"This was a calming, relaxing, and refreshing destination. There are unique places to visit nearby."
United States
Donna R.
The price is €200
includes taxes & fees
30 Oct - 31 Oct
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Smart TV, stereo
Charming home near Anna Maria Island with Jacuzzi
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!"
United States
Kyle S.
The price is €249
includes taxes & fees
3 Nov - 4 Nov
Charming home near Anna Maria Island with Jacuzzi
Property grounds
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
2.0 star property
10.0 out of 10, Exceptional, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is €305
includes taxes & fees
3 Nov - 4 Nov
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Outdoor dining
Kapok in Bradenton
Kapok in Bradenton
9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
United States
RHEA
The price is €416
includes taxes & fees
12 Nov - 13 Nov
Kapok in Bradenton
A heated pool
Enjoy a 3-bedroom vacation home in Yacht Club. Perfect home for family!
Enjoy a 3-bedroom vacation home in Yacht Club. Perfect home for family!
9.8 out of 10, Exceptional, (118)
"My husband and I had a very relaxing 10 days here. Very quiet neighborhood and close enough to ride the bikes to Cape Coral beach. "
United States
Leigh L.
The price is €354
includes taxes & fees
31 Oct - 1 Nov
Enjoy a 3-bedroom vacation home in Yacht Club. Perfect home for family!
Pool
Perfect Getaway with the pool
Perfect Getaway with the pool
10.0 out of 10, Exceptional, (26)
"We enjoyed our stay very much. Will stay again"
United States
Christi K.
The price is €305
includes taxes & fees
3 Nov - 4 Nov
Perfect Getaway with the pool
1 bedroom, iron/ironing board, travel cot, free WiFi
Historic Carriage House, 15 min to AMI Beach & IMG
Historic Carriage House, 15 min to AMI Beach & IMG
2.0 star property
10.0 out of 10, Exceptional, (10)
"Nice little spot close to downtown Bradenton. "
United States
Matt
The price is €209
includes taxes & fees
2 Nov - 3 Nov
Historic Carriage House, 15 min to AMI Beach & IMG
Fridge, microwave, oven, coffee/tea maker
Walk to Siesta key beach | Private Dock | Patio | Pool
Walk to Siesta key beach | Private Dock | Patio | Pool
9.4 out of 10, Exceptional, (14)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is €324
includes taxes & fees
3 Nov - 4 Nov
Walk to Siesta key beach | Private Dock | Patio | Pool
Outdoor pool, a heated pool
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
10.0 out of 10, Exceptional, (165)
"Clean and cute i will totally stay here again!"
United States
Anne F.
The price is €339
includes taxes & fees
1 Nov - 2 Nov
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
Pool
NEW!! The “WATERSIDE” COTTAGE~With dockage
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. "
United States
Ron R.
The price is €344
includes taxes & fees
3 Nov - 4 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage
Property grounds
Completely remodeled beautiful waterfront property on canal with dock
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"
United States
Jennifer R.
The price is €230
includes taxes & fees
3 Nov - 4 Nov
Completely remodeled beautiful waterfront property on canal with dock
Pool
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
9.6 out of 10, Exceptional, (53)
"Reasonably priced for our getaway. Located close enough for a short drive to the beach for us. The place was very clean. I would stay again!"
United States
Rachel B.
The price is €200
includes taxes & fees
30 Oct - 31 Oct
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
House
Hibiscus House Bed Breakfast Seashell Room
Hibiscus House Bed Breakfast Seashell Room
2.0 star property
The price is €228
includes taxes & fees
3 Nov - 4 Nov
Hibiscus House Bed Breakfast Seashell Room
Property grounds
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!
9.6 out of 10, Exceptional, (58)
"Peaceful - beautiful back yard area"
United States
Carmen R.
The price is €293
includes taxes & fees
1 Nov - 2 Nov
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!
Fridge, microwave, oven, stovetop
[lounge like locals] walk to siesta beach +bikes
[lounge like locals] walk to siesta beach +bikes
9.8 out of 10, Exceptional, (24)
"The property was very clean and conveniently located ."
United States
David
The price is €250
includes taxes & fees
30 Oct - 31 Oct
[lounge like locals] walk to siesta beach +bikes
Property grounds
Waterfront Getaway, a Boating Paradise
Waterfront Getaway, a Boating Paradise
10.0 out of 10, Exceptional, (44)
"Great place to stay with your boat."
United States
arthur n.
The price is €283
includes taxes & fees
30 Oct - 31 Oct
Waterfront Getaway, a Boating Paradise
Terrace/patio
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
10.0 out of 10, Exceptional, (66)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
The price is €221
includes taxes & fees
30 Oct - 31 Oct
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Fridge, microwave, oven, stovetop
Stylish house minutes from the beach
Stylish house minutes from the beach
9.6 out of 10, Exceptional, (25)
"Great location and safe neighborhood. Definitely will stay again if available."
United States
Luis M.
The price is €303
includes taxes & fees
2 Nov - 3 Nov
Stylish house minutes from the 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

Fairways Inn of Naples

Fairways Inn of Naples

10/10 Excellent
" Our favorite place to stay in Naples since 2023"
JASON 3-night trip
Posted 1 day ago
Fairways Inn of Naples

Find out more about Southwest Florida

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