Southwest Florida Holiday Rentals

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Our top choices for Southwest Florida holiday rentals

1. StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.2 out of 10, Wonderful, (184 reviews)
"Location was great."
United States
Joseph
The price is NZ$142
includes taxes & fees
18 Nov - 19 Nov
StudioRes by Marriott Fort Myers Airport

2. Lehigh Resort Club

Lehigh Resort Club
3.5 star property
Joel
9.0 out of 10, Wonderful, (132 reviews)
"Great place to relax"
United States
Juan
The price is NZ$236
includes taxes & fees
6 Dec - 7 Dec
Lehigh Resort Club

3. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,169 reviews)
"Upon arrival, the front desk was very helpful explaining everything in detail. The room was very clean & spacious and had everything we needed for our stay. The location on the beach and the view was AMAZING!! We would definitely stay here again…HIGHLY RECOMMEND!!!"
United States
Elizbeth
The price is NZ$523
includes taxes & fees
19 Nov - 20 Nov
Island Inn

4. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,057 reviews)
"Great resort and location!"
United States
Christine
The price is NZ$351
includes taxes & fees
29 Nov - 30 Nov
Tropical Beach Resorts

5. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,370 reviews)
"Great place to stay but comes with a price."
United States
John
The price is NZ$374
includes taxes & fees
30 Nov - 1 Dec
The Suites at Fishermen’s Village

6. Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
8.0 out of 10, Very good, (1,028 reviews)
"Cute, clean, beachside inn. Will definitely be back!"
United States
Emily
The price is NZ$304
includes taxes & fees
17 Nov - 18 Nov
Flamingo Inn

7. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,720 reviews)
"Great trip, beautiful island and great location!"
United States
Jeremy
The price is NZ$603
includes taxes & fees
29 Nov - 30 Nov
Sundial Beach Resort & Spa

8. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (299 reviews)
"Such a cute place that we have never heard of! Walked to cute tiny shops, got awesome bbq……… very quaint and quiet. Had a great time."
United States
Shannon
The price is NZ$397
includes taxes & fees
15 Nov - 16 Nov
Matlacha Tiny Village

9. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,967 reviews)
"Best place ever"
United States
Joshua
The price is NZ$375
includes taxes & fees
17 Nov - 18 Nov
Edison Beach House

10. Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (320 reviews)
"Debbie and Sean are excellent hosts. Very clean, very comfortable, very quiet. Pet friendly, which is awesome also. Great location also just a couple miles from downtown or the beach.."
United States
Joseph
The price is NZ$285
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn

11. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (987 reviews)
"Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities."
United States
Jennifer
The price is NZ$1,001
includes taxes & fees
12 Dec - 13 Dec
GullWing Beach Resort

12. Lakeside Oasis

Lakeside Oasis
2.0 star property
Iona
The price is NZ$448
includes taxes & fees
20 Nov - 21 Nov
Lakeside Oasis

13. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
United States
Canyon L.
The price is NZ$362
includes taxes & fees
15 Nov - 16 Nov
The "Grouper"

14. 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, (488 reviews)
"Location was perfect"
United States
Amylynn
The price is NZ$325
includes taxes & fees
9 Dec - 10 Dec
Pelican Post at Anna Maria Island Inn

15. Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.0 out of 10, Wonderful, (4 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
The price is NZ$728
includes taxes & fees
30 Nov - 1 Dec
Noel Real Estate

16. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (700 reviews)
"Enjoyed our stay"
United States
Robin
The price is NZ$374
includes taxes & fees
6 Dec - 7 Dec
A Beach Retreat

17. 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)
"Check in was easy, the cottage was clean and organized, the bed was very comfortable. "
United States
Jacob S.
The price is NZ$461
includes taxes & fees
15 Nov - 16 Nov
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

18. Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
East End
9.6 out of 10, Exceptional, (55 reviews)
"Loved this place! So private and cute! We walked to Wickies for breakfast and lunch and did Mudbugs for dinner! Best beaches were Blind Pass and Tarpon Bay! Make sure to use the code for a discount for Adventures in Paradise Shelling tours!"
United States
Stephen
The price is NZ$597
includes taxes & fees
16 Nov - 17 Nov
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

19. Lovers Key Resort Fort Myers Beach High floor Stunning Views Pool balcony

Lovers Key Resort Fort Myers Beach High floor Stunning Views Pool balcony
Fort Myers Beach
10.0 out of 10, Exceptional, (64 reviews)
"It had everything we needed & more! Views were amazing!!! We saw dolphins, loved the restaurant, and the pool!"
United States
Rose D.
The price is NZ$606
includes taxes & fees
6 Dec - 7 Dec
Lovers Key Resort Fort Myers Beach High floor Stunning Views Pool balcony

20. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,484 reviews)
"This place was perfect!"
United States
Kat
The price is NZ$276
includes taxes & fees
16 Nov - 17 Nov
Hibiscus Suites - Gateway to Siesta Key
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.

Find holiday rentals that suit your style

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$142 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.

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