A crowded beach with people sunbathing and swimming.

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
9.4 out of 10, Exceptional, (146 reviews)
"The place was very nice and clean and great location"
United States
Monica
The price is NZ$166
includes taxes & fees
4 Oct - 5 Oct
StudioRes by Marriott Fort Myers Airport

2. Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,089 reviews)
"Clean room, AC was Perfect, and deck view was amazing"
United States
Carlos
The price is NZ$499
includes taxes & fees
29 Sept - 30 Sept
Lovers Key Resort

3. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,921 reviews)
"Great stay."
United States
Angie
The price is NZ$321
includes taxes & fees
29 Sept - 30 Sept
Edison Beach House

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,156 reviews)
"Great location"
United States
Nicole
The price is NZ$402
includes taxes & fees
29 Sept - 30 Sept
Island Inn

5. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (975 reviews)
"Highly recommended, coastal by the sea, good for family outings."
United States
MARYTE
The price is NZ$930
includes taxes & fees
29 Sept - 30 Sept
GullWing Beach Resort

6. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (151 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is NZ$120
includes taxes & fees
29 Sept - 30 Sept
2 Queen Bed|Nsmk|Cape Coral FL

7. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is NZ$393
includes taxes & fees
30 Sept - 1 Oct
Matlacha Tiny Village

8. 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$688
includes taxes & fees
7 Oct - 8 Oct
Noel Real Estate

9. 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, (1,330 reviews)
"Excellent,clean y quiet"
United States
Carmen
The price is NZ$316
includes taxes & fees
6 Oct - 7 Oct
The Suites at Fishermen’s Village

10. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,335 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
The price is NZ$634
includes taxes & fees
29 Sept - 30 Sept
Bellasera Resort

11. Epic Arcades Heated Pool Home by Beach & Mercato

Epic Arcades Heated Pool Home by Beach & Mercato
Naples Park
10.0 out of 10, Exceptional, (114 reviews)
"GREAT location. Close to shopping, dining and the beach. Cute/clean house! Nice pool area. Would not hesitate in staying here again!"
United States
Tony A.
The price is NZ$927
includes taxes & fees
5 Oct - 6 Oct
Epic Arcades Heated Pool Home by Beach & Mercato

12. Experience your Dream Vacation Home

Experience your Dream Vacation Home
Ave Maria
10.0 out of 10, Exceptional, (21 reviews)
"This property is in a great neighborhood, peaceful, extremely convenient to Ave Maria University. Check-in and check-out instructions were very simple and easy to follow. We had everything we needed for our stay and felt very comfortable in this spacious home. Definitely hope to stay here again!"
United States
Jennifer M.
The price is NZ$921
includes taxes & fees
29 Sept - 30 Sept
Experience your Dream Vacation Home

13. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,310 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is NZ$359
includes taxes & fees
29 Sept - 30 Sept
Captiva Beach Resort

14. 2 Mi to Six Mile Preserve! Family Getaway w/ Pool

2 Mi to Six Mile Preserve! Family Getaway w/ Pool
3.0 star property
Fort Myers
The price is NZ$839
includes taxes & fees
30 Sept - 1 Oct
2 Mi to Six Mile Preserve! Family Getaway w/ Pool

15. 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$452
includes taxes & fees
29 Sept - 30 Sept
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

16. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (185 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is NZ$429
includes taxes & fees
30 Sept - 1 Oct
SeaSpray Resort

17. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,923 reviews)
"Amazing resort,"
United States
kurt
The price is NZ$316
includes taxes & fees
29 Sept - 30 Sept
Tropical Beach Resorts

18. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,702 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
The price is NZ$817
includes taxes & fees
29 Sept - 30 Sept
Sundial Beach Resort & Spa

19. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is NZ$374
includes taxes & fees
30 Sept - 1 Oct
The "Grouper"

20. Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is NZ$378
includes taxes & fees
29 Sept - 30 Sept
Nestled in North Port. Updated 2 Bed / 1 Bath.
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southwest Florida holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southwest Florida. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southwest Florida. Seeing all the best attractions is bound to make you fall in love with Southwest Florida. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southwest Florida short-term rentals, that won’t be hard to do.

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