Holiday Homes in Southwest Florida

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Our top choices for Southwest Florida holiday homes

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
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, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is €308
includes taxes & fees
12 May - 13 May
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, (23 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is €192
includes taxes & fees
3 May - 4 May
Nestled in North Port. Updated 2 Bed / 1 Bath.

Hibiscus House Bed Breakfast Citrus Room

Hibiscus House Bed Breakfast Citrus Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely beautiful room and amenities and the breakfast was delicious and with so many options. Loved the communication and cannot wait to come back! "
United States
Crissa
The price is €233
includes taxes & fees
5 May - 6 May
Hibiscus House Bed Breakfast Citrus Room

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
Bradenton
10.0 out of 10, Exceptional, (14 reviews)
"Great spot, lovely back yard and pool, so relaxing we loved it."
United States
Cadence
The price is €358
includes taxes & fees
18 May - 19 May
Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Lakeside Retreat with Heated Pool

Lakeside Retreat with Heated Pool
Hancock
7.6 out of 10, Good, (37 reviews)
"The front door code lock worked when it wanted too. Forcing us to lock the front door and use the back door and walk around. Except when that door stopped working. Bugs found in the master bath in 2 different areas that we had to spray and wipe up. Yes, I understand its Florida but still. However the bed sheets were clean, lots of pillow choices, and towels to use. Property could use a refresh, its been beaten up a bit through the rentals but a good deal on price for what you receive. Pool...
United States
John
The price is €372
includes taxes & fees
29 Apr - 30 Apr
Lakeside Retreat with Heated Pool

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, (75 reviews)
"Very clean, the host was very good at communication. We were there for an event so we wouldn't have to drive back to Tampa. It was a seamless stay. The host had snacks and small fridge and freezer, coffee maker, air fryer and microwave. It was a older and a little dated, but clean and just what we needed. We would stay again."
United States
Paul Vance R.
The price is €161
includes taxes & fees
29 Apr - 30 Apr
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is €299
includes taxes & fees
4 May - 5 May
[escape to paradise] siesta key beach getaway

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Sunny Shores
9.4 out of 10, Exceptional, (39 reviews)
"Excellent for a family trip."
United States
RHEA
The price is €429
includes taxes & fees
29 May - 30 May
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

"Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (31 reviews)
" Clean, easy to get to, well stocked with towels, beach towels, etc. Gorgeous outdoor seating and pool. Would stay again. "
United States
Danielle W.
The price is €314
includes taxes & fees
30 Apr - 1 May
"Stingray" 3 miles to Anna Marie

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 €293
includes taxes & fees
29 Apr - 30 Apr
Home in quiet Bird Sanctuary Neighborhood, close to Beach

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, (39 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.
The price is €219
includes taxes & fees
29 Apr - 30 Apr
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

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.
Southgate
10.0 out of 10, Exceptional, (74 reviews)
"Wonderful Stay"
United States
Christopher R.
The price is €229
includes taxes & fees
29 Apr - 30 Apr
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Tropical Mango Grove Stay Whiskey Creek Area

Tropical Mango Grove Stay Whiskey Creek Area
2.0 star property
McGregor
The price is €241
includes taxes & fees
28 May - 29 May
Tropical Mango Grove Stay Whiskey Creek Area

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, (22 reviews)
"This is the most gorgeous house and so charming! Just lovely and relaxing!"
United States
Colleen P.
Charming 2-bedroom house in lovely Sarasota with yard.

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.
The price is €235
includes taxes & fees
4 May - 5 May
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.5 star property
Fort Myers
The price is €300
includes taxes & fees
30 Apr - 1 May
Bright & Cozy Townhome · Pool & Near Downtown

"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>

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, (43 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
The price is €215
includes taxes & fees
29 Apr - 30 Apr
Swimming pool, lake view, minutes to Naple's downtown and beach.

Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway
Bradenton
10.0 out of 10, Exceptional, (142 reviews)
"Great property, wonderful and responsive host"
United States
Erik H.
The price is €353
includes taxes & fees
11 May - 12 May
Paradise Cove -- A perfect Beach Getaway
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
614
Accommodation
1051 Holiday Homes
Lowest Price
€161
Highest Price
€429

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