Southwest Florida Holiday Rentals

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Our top choices for Southwest Florida holiday rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (283 reviews)
"Great place to stay!!!"
United States
Tara
The price is AU$184
includes taxes & fees
11 June - 12 June
Kon Tiki Inn

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, (1,225 reviews)
"Great location clean and specious"
United States
Kathryn
The price is AU$296
includes taxes & fees
6 June - 7 June
The Suites at Fishermen’s Village- 2 Bedroom Suites

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,766 reviews)
"Loved the pool and being close to the beach, restaurants and shopping. We will definitely stay again next year."
United States
Jenifer
The price is AU$310
includes taxes & fees
7 June - 8 June
Edison Beach House

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,262 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is AU$348
includes taxes & fees
7 June - 8 June
Captiva Beach Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,535 reviews)
"Clean room and convenient to the beach."
United States
Jacqueline
The price is AU$331
includes taxes & fees
8 June - 9 June
Tropical Beach Resorts

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,136 reviews)
"The place was amazing and the host was very gracious."
United States
Wendy
The price is AU$452
includes taxes & fees
25 June - 26 June
Island Inn

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
8.0 out of 10, Very good, (3 reviews)
"I was extremely disappointed with this property. There was mold visible on the outside of the door, and the inside floors were absolutely filthy and appeared not to have been properly cleaned. The bathtub had pubic hair in it, and the shower was also dirty and unsanitary. I called to report the issues and requested to be moved to a different property. The representative who answered said she would call me back, but I didn't receive a return call until six hours later. By that time, I had no...
United States
Suzette
The price is AU$537
includes taxes & fees
8 June - 9 June
Cedar Run Resort - Roam Hospitality

Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.4 out of 10, Exceptional, (3 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
The price is AU$599
includes taxes & fees
5 June - 6 June
Noel Real Estate

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"This is a great space. Quiet, serene, clean, comfortable and close to what you need. Our family of three had a great stay and highly recommend!"
United States
Taletha
The price is AU$561
includes taxes & fees
8 June - 9 June
MALU LANI Inn & Marina

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (639 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is AU$320
includes taxes & fees
7 June - 8 June
A Beach Retreat

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,326 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is AU$235
includes taxes & fees
7 June - 8 June
Hibiscus Suites - Gateway to Siesta Key

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,654 reviews)
"Excellent stay and amenities for families. "
United States
Megan
The price is AU$708
includes taxes & fees
5 July - 6 July
Sundial Beach Resort & Spa

Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,055 reviews)
"Always a great stay"
United States
Jason
The price is AU$446
includes taxes & fees
6 June - 7 June
Lovers Key Resort

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (482 reviews)
"Great location. Friendly staff nice pool Too much fabric softener fragrance in the linens"
United States
Marianne
Venice Beach Villas

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!
3.0 star property
Pelican
10.0 out of 10, Exceptional, (1 review)
"This place was wonderful! The host is quick to respond to any questions. Cleanliness excellent. The kitchen has anything and everything you could possibly need. We would highly recommend It. Also is a convenient location to the beaches and downtown Cape Coral. We lived in Fort Myers and Cape Coral before hurricane Ian so we were familiar with the area. It’s also located in a very nice neighborhood. Thankyou for a great stay🍊☀️"
United States
Michael
The price is AU$506
includes taxes & fees
19 June - 20 June
Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,278 reviews)
"best hotel at naples"
United States
Carlos
The price is AU$458
includes taxes & fees
7 June - 8 June
Bellasera Resort

Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
LaBelle
9.8 out of 10, Exceptional, (86 reviews)
"Peaceful, loved listening to the cows and roosters in the early morning while sitting on the porch drinking our coffee.Daily visits from the dog’s were a plus. Sleeping in the hammock and sitting by the fire was very relaxing for my wife and I. Our host was also responsive in a timely manner . We hope to visit again soon ! "
United States
Fred F.
The price is AU$357
includes taxes & fees
5 June - 6 June
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (804 reviews)
"Centrally located, all the staff was excellent. Great place to stay! Will stay here again!"
United States
Keri
The price is AU$495
includes taxes & fees
7 June - 8 June
Bridgewalk Resort

Emerald Entry Retreat

Emerald Entry Retreat
2.0 star property
LaBelle
The price is AU$605
includes taxes & fees
17 June - 18 June
Emerald Entry Retreat

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.5 star property
Fort Myers
The price is AU$497
includes taxes & fees
5 June - 6 June
Bright & Cozy Townhome · Pool & Near Downtown
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$184 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.