Southwest Florida vacation rentals

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Latest Southwest Florida vacation rental deals

MOST POPULARSarasota
Vacation homes from $36
Naples
Vacation homes from $79
Siesta Key
Vacation homes from $89
Fort Myers
Vacation homes from $33
Marco Island
Vacation homes from $126
Fort Myers Beach
Vacation homes from $118

Best Southwest Florida vacation rentals

Most recommended vacation rentals in Southwest Florida

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An Island Getaway at Palm Tree Villas - Holmes Beach - Beach
An Island Getaway at Palm Tree Villas
Holmes Beach, FL
8.9Very good(203)
Parking
Free Wi-Fi
Pool
$565+
Check availability
Updated South Seas Villa with Pool and Private Beach - Captiva - Pool
Updated South Seas Villa with Pool and Private Beach
Captiva, FL
8.8Very good(13)
Parking
Free Wi-Fi
Pool
Spa
$346+
Check availability
Siesta Heron Suites & Villas - Siesta Key - Living room
Siesta Heron Suites & Villas
Siesta Key, FL
8.4Very good(306)
Free Wi-Fi
Pool
$291+
Check availability
Lantana Suite - Captiva - Balcony
Lantana Suite
Captiva, FL
8.5Very good(2)
Parking
Free Wi-Fi
Pet friendly
$585+
Check availability
Seahorse Suite home - Bradenton Beach - Beach
Seahorse Suite home
Bradenton Beach, FL
9.0Wonderful(6)
Free Wi-Fi
Pet friendly
$339+
Check availability
Captain's Quarters By Ami Locals - Bradenton Beach - Pool
Captain's Quarters By Ami Locals
Bradenton Beach, FL
7.9Good(88)
Parking
Free Wi-Fi
Pool
Pet friendly
$495+
Check availability
Marco Beach Vacation Suites - Marco Island - Balcony
Marco Beach Vacation Suites
Marco Island, FL
7.0Good(3)
Free Wi-Fi
Pool
$269+
Check availability
Gorgeous South Seas Villa with Pool and Private Beach - Captiva - Living room
Gorgeous South Seas Villa with Pool and Private Beach
Captiva, FL
8.2Very good(11)
Parking
Free Wi-Fi
Pool
$341+
Check availability
Burnt Store Marina Condo Boat, Swim, Golf! - Punta Gorda - Living room
Burnt Store Marina Condo Boat, Swim, Golf!
Punta Gorda, FL
8.0Very good(23)
Free Wi-Fi
$129+
Check availability
Gorgeous Newly Renovated Marina Front Condo - Captiva - Living room
Gorgeous Newly Renovated Marina Front Condo
Captiva, FL
9.5Wonderful(2)
Parking
Free Wi-Fi
Pool
$414+
Check availability
Alamanda Villa on Holmes Beach - Holmes Beach
Alamanda Villa on Holmes Beach
Holmes Beach, FL
8.7Very good(332)
Parking
Free Wi-Fi
Pool
Pet friendly
$470+
Check availability
Villa #6 Starfish - Holmes Beach
Villa #6 Starfish
Holmes Beach, FL
7.3Good(4)
Parking
Free Wi-Fi
Pool
Pet friendly
$649+
Check availability
Sunrise Garden Resort - Anna Maria
Sunrise Garden Resort
Anna Maria, FL
7.7Good(349)
Free Wi-Fi
Pool
Pet friendly
$353+
Check availability
Stunning Beachfront Residence at South Seas Resort - Captiva
Stunning Beachfront Residence at South Seas Resort
Captiva, FL
9.2Wonderful(6)
Parking
Free Wi-Fi
Pool
$485+
Check availability
Villa #2 Shrimp - Holmes Beach
Villa #2 Shrimp
Holmes Beach, FL
10Wonderful(1)
Parking
Free Wi-Fi
Pool
Pet friendly
$568+
Check availability
Villa #5 Seashell - Holmes Beach
Villa #5 Seashell
Holmes Beach, FL
9.0Wonderful(4)
Parking
Free Wi-Fi
Pool
Pet friendly
$714+
Check availability
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Property Types

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

August

High season

March

Average price (weeknight)

$377

Average price (weekend night)

$406
Cheapest month to stay with an average 23% drop in price.
Most expensive month to stay with an average 17% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Southwest Florida vacation rental

  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Southwest Florida for 10 days.
  • The cheapest Southwest Florida vacation rental found on KAYAK in the last 2 weeks was $74, while the most expensive was $890.
  • Vacation rentals in Southwest Florida are around 33% more expensive than hotels on average. Search here to compare prices for all accommodation types in Southwest Florida.
  • The city in Southwest Florida with the most affordable vacation homes is North Fort Myers, with around 146 properties and an average price of $67. The most popular vacation rentals in Southwest Florida among KAYAK users are Pet-Friendly Fort Myers Home with Patio and Grill!, Private Pool Family-Friendly Cape Coral Retreat!, and Shroom life farm Chicken shack.
See more tips

FAQs when booking a vacation home in Southwest Florida

  • How much is a vacation rental in Southwest Florida for tonight?

    In the last 72 hours, users have found Southwest Florida vacation rentals for tonight for as low as $69. Search here for similar prices

  • How much is a vacation rental for a week in Southwest Florida?

    The average price for a weekly Southwest Florida vacation rental found by KAYAK users in the last 2 weeks is $2,509.

  • How much is a vacation rental for a month in Southwest Florida?

    The average price for a monthly Southwest Florida vacation rental found by KAYAK users in the last 2 weeks is $10,753.

  • What types of vacation rentals are available in Southwest Florida?

    There are loads of different property types that you can make your vacation home in Southwest Florida. You’ll find apartments, cabins, condos, houses, homestays, villas, cottages, bungalows, caravans, holiday parks, houseboats, chalets, castles, luxury tents, farm stays, lodges, recreational vehicles, campgrounds, agritourism, boats, treehouses, caravan parks and barns.

  • What are some of the most-loved vacation rentals available in Southwest Florida?

    There are many types of properties available for Southwest Florida vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Marco Beach Vacation Suites and Econo Lodge North.

  • What are the most popular Southwest Florida vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Parkshore resort apartment and Catina Golf Condo at the Lely Resort.

  • Are there any pet-friendly vacation rentals in Southwest Florida?

    There are a number of dog and pet-friendly Southwest Florida vacation rentals, with around 15% allowing you to bring your pet along with you.

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Where to stay in Southwest Florida?

Our map will help you find the perfect place to stay in Southwest Florida by showing you the exact location of each vacation home.

Everything you need to know for your stay in Southwest Florida

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