Southwest Florida Holiday Rentals

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Our top choices for Southwest Florida holiday rentals

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,115 reviews)
"Beautiful rooms and perfect location!!"
United States
Olivia Rose
The price is AU$334
includes taxes & fees
2 Apr - 3 Apr
The Suites at Fishermen’s Village- 2 Bedroom Suites

Marriott's Crystal Shores

Marriott's Crystal Shores
3.5 star property
South End
9.2 out of 10, Wonderful, (225 reviews)
"Hotel is well maintained and has beautiful grounds and beach"
United States
Chris
The price is AU$1,869
includes taxes & fees
6 Mar - 7 Mar
Marriott's Crystal Shores

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,603 reviews)
"Room was clean and was cleaned in the middle of our stay and staff was great."
United States
Glen
The price is AU$889
includes taxes & fees
8 Mar - 9 Mar
Sundial Beach Resort & Spa

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (95 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is AU$978
includes taxes & fees
8 Mar - 9 Mar
SeaSpray Resort

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,666 reviews)
"Location and suite amenities were perfect "
United States
Robert
Edison Beach House

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,131 reviews)
"Everything was wonderful."
United States
Walter
The price is AU$695
includes taxes & fees
28 Mar - 29 Mar
Island Inn

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,208 reviews)
"Staff really were accommodating. The location was perfect and the rooms were clean and quiet. We enjoyed the pool and beach."
United States
Glenn
The price is AU$478
includes taxes & fees
2 Apr - 3 Apr
Captiva Beach Resort

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (83 reviews)
"Very nice room with great beachside gulf views."
United States
PEGGY
Seabreeze at Anna Maria Island Inn

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,338 reviews)
"Wonderful stay!"
United States
Victoria
The price is AU$400
includes taxes & fees
5 Mar - 6 Mar
Tropical Beach Resorts

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (258 reviews)
"Great place! "
United States
Michelle
The price is AU$263
includes taxes & fees
2 Apr - 3 Apr
Kon Tiki Inn

Christian Retreat Conference Center

Christian Retreat Conference Center
3.0 star property
Bradenton
9.6 out of 10, Exceptional, (4 reviews)
"A bargain given the cost of other hotels. Nice being hosted by Christians!"
United States
Patrick
The price is AU$183
includes taxes & fees
29 Mar - 30 Mar
Christian Retreat Conference Center

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (431 reviews)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
Haley's at The Anna Maria Island Inn

StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.2 out of 10, Wonderful, (30 reviews)
"Loved stay here!!! "
United States
Melissa
The price is AU$201
includes taxes & fees
4 Apr - 5 Apr
StudioRes by Marriott Fort Myers Airport

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (277 reviews)
"The property was super cute and clean! It also had just about anything you could need!"
United States
Wyatt
The price is AU$352
includes taxes & fees
10 Mar - 11 Mar
Matlacha Tiny Village

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (371 reviews)
"Room was clean and great location."
United States
Jennifer
Pelican Post at Anna Maria Island Inn

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (599 reviews)
"The location is ideal, rooms are nice and the owners are extremely accommodating. "
United States
Catherine
A Beach Retreat

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,246 reviews)
"We love everything about this property and stay here whenever we're in Naples."
United States
Sarah
Bellasera Resort

River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (280 reviews)
"Staff was very helpful. Room was clean and comfortable. Setting is very nice. "
United States
Martin
The price is AU$448
includes taxes & fees
6 Mar - 7 Mar
River Wilderness Waterfront Cabins

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,263 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
The price is AU$450
includes taxes & fees
2 Apr - 3 Apr
Hibiscus Suites - Gateway to Siesta Key

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.0 out of 10, Wonderful, (8 reviews)
"I loved the location, for a couple the place is wonderful, I would only request, 2 nice beach chairs and an umbrella. Great communication, clean, we will come back for sure. "
United States
Lourdes
The price is AU$1,226
includes taxes & fees
5 Mar - 6 Mar
Alamanda Villas
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$214 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.