Southwest Florida Holiday Rentals

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Holiday Rentals in Southwest Florida

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5041)
"Great place and loved the closeness to the beach!"
United States
Nadine
The price is AU$255
includes taxes & fees
20 Oct - 21 Oct
Tropical Beach Resorts
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (1007)
"Fantastic place to stay! Everything was top notch! "
United States
Julie
The price is AU$302
includes taxes & fees
20 Oct - 21 Oct
The Suites at Fishermen’s Village- 2 Bedroom Suites
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (265)
"Very nice place with all necesary accommodations for a Pleasant stay. "
United States
isabel
The price is AU$315
includes taxes & fees
20 Oct - 21 Oct
Matlacha Tiny Village
Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (238)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
United States
Carla
The price is AU$262
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2180)
"Friendly staff, room was really clean!"
United States
Zasha
Hibiscus Suites - Gateway to Siesta Key
Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (667)
"great trip and great stay"
United States
Annamarie
The price is AU$269
includes taxes & fees
17 Nov - 18 Nov
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1143)
"Great place close to the beach"
United States
Yuditza
Captiva Beach Resort
Wiggins Pass Chalet
4.0 star property
9.6 out of 10, Exceptional, (234)
"Great parking, friendly and attentive staff, clean property, and it is near everything we need. Good spot for a family vacationing. "
United States
marcos
Wiggins Pass Chalet
Island Inn
3.5 star property
9.4 out of 10, Exceptional, (1110)
"A great place to enjoy the beach. Beautiful sunsets, We will definitely be back to Island Inn. Thanks for a great vacation!!!"
United States
Dave
The price is AU$444
includes taxes & fees
26 Oct - 27 Oct
Island Inn
Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (378)
"The staff members were so nice and super helpful!! Place was so cute! "
United States
Whitley
Haley's at The Anna Maria Island Inn
GullWing Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (930)
"The view of the beach was spectacular. "
United States
Carol
GullWing Beach Resort
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (308)
"Great location"
United States
Michael
Pelican Post at Anna Maria Island Inn
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1533)
"All around great place to stay"
United States
David
Edison Beach House
Lovers Key Resort
3.0 star property
8.8 out of 10, Excellent, (1009)
"We enjoyed the pool and watching the dolphins from bay front."
United States
Cristine
Lovers Key Resort
Alamanda Villas
3.5 star property
10.0 out of 10, Exceptional, (2)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
The price is AU$708
includes taxes & fees
20 Oct - 21 Oct
Alamanda Villas
Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (332)
"We had a great time at Tiny House, location can not be better and everything was as described."
United States
Elvia
The price is AU$267
includes taxes & fees
20 Oct - 21 Oct
Tiny House Siesta
5 Mi to Dtwn: Family Getaway in Punta Gorda
3.0 star property
The price is AU$179
includes taxes & fees
24 Oct - 25 Oct
5 Mi to Dtwn: Family Getaway in Punta Gorda
SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (52)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is AU$398
includes taxes & fees
20 Oct - 21 Oct
SeaSpray Resort
Family Retreat w/ Heated Pool in Port Charlotte!
3.0 star property
The price is AU$600
includes taxes & fees
23 Oct - 24 Oct
Family Retreat w/ Heated Pool in Port Charlotte!
GreenLinks Golf Villas at Lely Resort
3.0 star property
9.4 out of 10, Exceptional, (532)
"Great location. Easy and very friendly check-in"
United States
Michael
GreenLinks Golf Villas at Lely Resort
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

Everything you need to know about Southwest Florida holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Florida holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Florida holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southwest Florida holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Florida. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Florida holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest Florida holiday rentals we have selected for you start as low as AU$212 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southwest Florida rentals

At Expedia, we put the best Southwest Florida holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest Florida rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Florida holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Florida. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.