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, (1,203 reviews)
"We had a great stay!!"
United States
Rebecca
The price is NZ$359
includes taxes & fees
9 June - 10 June
The Suites at Fishermen’s Village- 2 Bedroom Suites

StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.4 out of 10, Exceptional, (54 reviews)
"Great hotel and free clean and friendly staff"
United States
cynthia
The price is NZ$158
includes taxes & fees
20 May - 21 May
StudioRes by Marriott Fort Myers Airport

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (276 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is NZ$217
includes taxes & fees
1 June - 2 June
Kon Tiki Inn

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,747 reviews)
"Room was great, view was amazing!"
United States
Ashley
The price is NZ$472
includes taxes & fees
20 May - 21 May
Edison Beach House

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,483 reviews)
"Loved our stay, room was beautiful and bed was so comfy! So close to the beach, perfect location. Would definitely stay again!"
United States
Amberly
The price is NZ$350
includes taxes & fees
20 May - 21 May
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,311 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is NZ$304
includes taxes & fees
26 May - 27 May
Hibiscus Suites - Gateway to Siesta Key

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (272 reviews)
"Clean room, stuff very friendly, easy access to rooms, close to everything"
United States
RITA
The price is NZ$236
includes taxes & fees
6 June - 7 June
Wiggins Pass Chalet

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (798 reviews)
"Overall a pretty good spot. Friendly and helping staff, clean area, own parking lot"
United States
Celeste
The price is NZ$548
includes taxes & fees
3 June - 4 June
Bridgewalk Resort

Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,049 reviews)
"Very nice, will stay there again."
United States
Duane
The price is NZ$503
includes taxes & fees
1 June - 2 June
Lovers Key Resort

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (284 reviews)
"Excellent stay. Only complaint was this single ply toilet paper parking was good. Had a nice back patio air-conditioned worked great. Would definitely go back"
United States
Dean
The price is NZ$163
includes taxes & fees
21 May - 22 May
Lazy Cuckoo Inn

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (633 reviews)
"Love this place"
United States
Marialis
The price is NZ$378
includes taxes & fees
18 May - 19 May
A Beach Retreat

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (287 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is NZ$445
includes taxes & fees
17 May - 18 May
Matlacha Tiny Village

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,134 reviews)
"The place was amazing and the host was very gracious."
United States
Wendy
The price is NZ$656
includes taxes & fees
19 May - 20 May
Island Inn

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 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 NZ$679
includes taxes & fees
17 May - 18 May
MALU LANI Inn & Marina

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (945 reviews)
"Great location right on the beach."
United States
Adrian
The price is NZ$884
includes taxes & fees
17 May - 18 May
GullWing Beach Resort

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,268 reviews)
"Great accommodations , very clean and Great Service We will certainly return. "
United States
Phillip
The price is NZ$434
includes taxes & fees
7 June - 8 June
Bellasera Resort

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 NZ$733
includes taxes & fees
17 May - 18 May
Noel Real Estate

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,250 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is NZ$452
includes taxes & fees
17 May - 18 May
Captiva Beach Resort

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, (449 reviews)
"Great location, clean and quiet. "
United States
Sara
The price is NZ$506
includes taxes & fees
17 May - 18 May
Haley's at The Anna Maria Island Inn

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, (402 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
The price is NZ$516
includes taxes & fees
19 May - 20 May
Pelican Post at Anna Maria Island Inn
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$217 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.