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, (271 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
The price is AU$195
includes taxes & fees
5 May - 6 May
Kon Tiki Inn

Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,046 reviews)
"Very nice, will stay there again."
United States
Duane
The price is AU$406
includes taxes & fees
13 May - 14 May
Lovers Key Resort

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
The price is AU$179
includes taxes & fees
11 May - 12 May
Venice Beach Villas

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,720 reviews)
"perfect location in the midst of Time Square activity. looking foward to another stay"
United States
Mary
The price is AU$369
includes taxes & fees
4 May - 5 May
Edison Beach House

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is AU$558
includes taxes & fees
27 Apr - 28 Apr
MALU LANI Inn & Marina

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (943 reviews)
"Wonderful stay"
United States
Doug
The price is AU$718
includes taxes & fees
3 May - 4 May
GullWing Beach Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,238 reviews)
"Clean and very close to beach. "
United States
Daniel
The price is AU$329
includes taxes & fees
26 Apr - 27 Apr
Captiva Beach Resort

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (622 reviews)
"Love this place"
United States
Marialis
The price is AU$268
includes taxes & fees
3 May - 4 May
A Beach Retreat

4 Mi to Siesta Key Beach: Condo w/ Private Patio

4 Mi to Siesta Key Beach: Condo w/ Private Patio
3.5 star property
Sarasota
4 Mi to Siesta Key Beach: Condo w/ Private Patio

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, (1,176 reviews)
"Clean place Staff was friendly Place was fun "
United States
LaRae
The price is AU$357
includes taxes & fees
26 Apr - 27 Apr
The Suites at Fishermen’s Village- 2 Bedroom Suites

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,429 reviews)
"We had a very nice time and the resort was centrally located and right down the road from the beach. "
United States
Christopher Kevin
The price is AU$343
includes taxes & fees
3 May - 4 May
Tropical Beach Resorts

Hibiscus House Bed Breakfast Inn Parrot Room

Hibiscus House Bed Breakfast Inn Parrot Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in, clean room and very close to many restaurants and bars"
United States
david
The price is AU$337
includes taxes & fees
22 Apr - 23 Apr
Hibiscus House Bed Breakfast Inn Parrot Room

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (247 reviews)
"Staff very accommodating."
United States
Genevieve
The price is AU$299
includes taxes & fees
23 Apr - 24 Apr
Tropical Villas of Venice Beach

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, (83 reviews)
"The cottage was very clean. It is exactly as described. The host was extremely responsive and very helpful."
United States
Silvana C.
The price is AU$356
includes taxes & fees
21 Apr - 22 Apr
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Lido Key
9.8 out of 10, Exceptional, (124 reviews)
"Super clean, perfect location, and cool decor - and, most important, veeerry comfortable beds! We loved our stay! "
United States
Kevin L.
The price is AU$411
includes taxes & fees
23 Apr - 24 Apr
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and the perfect location! Close to the beach, restaurants, and the grocery! We loved the heated pool in February. "
United States
Robert
The price is AU$633
includes taxes & fees
7 May - 8 May
Alamanda Villas

Lovely Condo! IMG Academy 5 Min · Anna Maria Island · Heated Pools & Hot Tubs

Lovely Condo! IMG Academy 5 Min · Anna Maria Island · Heated Pools & Hot Tubs
Bradenton
10.0 out of 10, Exceptional, (124 reviews)
"We enjoyed our stay. Is as shown in pictures and description. "
United States
Erin M.
The price is AU$446
includes taxes & fees
21 Apr - 22 Apr
Lovely Condo! IMG Academy 5 Min · Anna Maria Island · Heated Pools & Hot Tubs

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.0 star property
Fort Myers
The price is AU$481
includes taxes & fees
21 Apr - 22 Apr
Bright & Cozy Townhome · Pool & Near Downtown

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,289 reviews)
"Clean room, quiet and in a location convenient to Siesta Key. The pool is very nice, although located at the front of the property alongside a busy road. Would definitely recommend this hotel, especially if a kitchenette is desired."
United States
CAROLYN
The price is AU$237
includes taxes & fees
22 Apr - 23 Apr
Hibiscus Suites - Gateway to Siesta Key

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (789 reviews)
"So nice to walk to restaurants and shops. Very walkable. Clean. Updated and relaxing atmosphere. Parking was really convenient and accessible. Would stay again."
United States
Deborah
The price is AU$430
includes taxes & fees
3 May - 4 May
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 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$132 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.