Southwest Florida Holiday Rentals

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Holiday Rentals in Southwest Florida

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5096)
"The room was clean and the staff was very nice."
United States
Jill
The price is NZ$319
includes taxes & fees
16 Nov - 17 Nov
Tropical Beach Resorts

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4.0 star property
Bonita Springs
9.2 out of 10, Wonderful, (702)
"great staff, nice rooms, quiet and pleasant get away"
United States
Andy
The price is NZ$299
includes taxes & fees
15 Dec - 16 Dec
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1156)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort

Pelican Post at Anna Maria Island Inn

3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (317)
"Great location"
United States
Michael
The price is NZ$490
includes taxes & fees
30 Nov - 1 Dec
Pelican Post at Anna Maria Island Inn

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (294)
"Fun place to stay for family vacation "
United States
Todd
The price is NZ$768
includes taxes & fees
8 Dec - 9 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (243)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is NZ$302
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn

Edison Beach House

3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1554)
"All around great place to stay"
United States
David
The price is NZ$359
includes taxes & fees
17 Nov - 18 Nov
Edison Beach House

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2193)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key

GullWing Beach Resort

3.5 star property
South Island
9.4 out of 10, Exceptional, (932)
"Great location"
United States
Andrey
GullWing Beach Resort

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is NZ$473
includes taxes & fees
19 Nov - 20 Nov
The Inn On Siesta Key

Lovers Key Resort

3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1012)
"The attention was excellent,very polite staff definitely I m going back with my family thank you"
United States
Antonio
Lovers Key Resort

Matlacha Tiny Village

3.0 star property
Matlacha
8.8 out of 10, Excellent, (265)
"Amazing spot. Love it. Quiet, and very suitable for us. The hosts are amazing; they will do anything in their power to accommodate your needs. Highly recommend it."
United States
Isabel
The price is NZ$362
includes taxes & fees
16 Nov - 17 Nov
Matlacha Tiny Village

Haley's at The Anna Maria Island Inn

3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (390)
"Shampoos conditioners and lotions, beach towels, cleanliness freshness, thank you it was a good day"
United States
Karen
Haley's at The Anna Maria Island Inn

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1027)
"We loved our stay and plan on returning. Loved the sunset cruise from the marina "
United States
Paul
The price is NZ$413
includes taxes & fees
16 Nov - 17 Nov
The Suites at Fishermen’s Village- 2 Bedroom Suites

Wiggins Pass Chalet

4.0 star property
Naples
9.6 out of 10, Exceptional, (236)
"Room was very clean, staff was awesome, and the location was perfect. I will definitely stay here again."
United States
Tamisha
Wiggins Pass Chalet

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (571)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very good, (342)
"Enjoyable stay. "
United States
Lori
The price is NZ$413
includes taxes & fees
17 Nov - 18 Nov
Tiny House Siesta

StudioRes Fort Myers Airport

3.0 star property
Fort Myers
8.4 out of 10, Very good, (8)
"Clean room, staff, amenities, easy check in, easy access to gas stations, restaurants, and retail. "
United States
Gina
The price is NZ$185
includes taxes & fees
15 Dec - 16 Dec
StudioRes Fort Myers Airport

Island Inn

3.5 star property
West End
9.4 out of 10, Exceptional, (1116)
"Really nice, updated, and clean room with a screened waterfront balcony in a perfect place on the island (far enough away from the big resorts to be in a quieter area, but close enough to the center area of the island to be convenient). "
United States
Chris
The price is NZ$472
includes taxes & fees
18 Nov - 19 Nov
Island Inn

Bridgewalk Resort

3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (759)
"Great stay!"
United States
Sufyan
The price is NZ$567
includes taxes & fees
15 Dec - 16 Dec
Bridgewalk 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 favorite 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 depends 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 NZ$161 per night. Entering your travel dates in the search wizard you might find 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.