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
9.2 out of 10, Wonderful, (110 reviews)
"Great stay."
United States
cynthia
The price is NZ$135
includes taxes & fees
19 Aug - 20 Aug
StudioRes by Marriott Fort Myers Airport

2. 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, (1,296 reviews)
"Great location and love the shops being under us. Great view and food options."
United States
Nathaniel
The price is NZ$335
includes taxes & fees
18 Aug - 19 Aug
The Suites at Fishermen’s Village- 2 Bedroom Suites

3. Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village
3.0 star property
Fort Myers
9.6 out of 10, Exceptional, (27 reviews)
"Great place to stay"
United States
Rachel
The price is NZ$419
includes taxes & fees
23 Aug - 24 Aug
Landing Apartments Fort Myers near Eastwood Village

4. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,868 reviews)
"Lovely stay. Right on a beautiful beach. Located near food, shopping etc. Great place to stay."
United States
Brian
The price is NZ$375
includes taxes & fees
16 Aug - 17 Aug
Edison Beach House

5. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,684 reviews)
"Clean room and beach view"
United States
Carla
The price is NZ$849
includes taxes & fees
31 Aug - 1 Sept
Sundial Beach Resort & Spa

6. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,145 reviews)
"Great views, clean room, amazing beach and staff!!! Can't wait to come."
United States
Daniel
The price is NZ$379
includes taxes & fees
24 Aug - 25 Aug
Island Inn

7. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (965 reviews)
"We really enjoyed our stay here and plan on staying here again!"
United States
Claudia
The price is NZ$957
includes taxes & fees
1 Sept - 2 Sept
GullWing Beach Resort

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,404 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is NZ$243
includes taxes & fees
26 Aug - 27 Aug
Hibiscus Suites - Gateway to Siesta Key

9. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is NZ$717
includes taxes & fees
16 Aug - 17 Aug
Cedar Run Resort - Roam Hospitality

10. 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$437
includes taxes & fees
14 Aug - 15 Aug
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

11. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,297 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is NZ$347
includes taxes & fees
17 Aug - 18 Aug
Captiva Beach Resort

12. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,321 reviews)
"The perfect place for a family vacation"
United States
Lorenzo
The price is NZ$472
includes taxes & fees
17 Aug - 18 Aug
Bellasera Resort

13. 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$829
includes taxes & fees
17 Aug - 18 Aug
Epic Arcades Heated Pool Home by Beach & Mercato

14. 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$681
includes taxes & fees
22 Aug - 23 Aug
Noel Real Estate

15. 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$375
includes taxes & fees
16 Aug - 17 Aug
Nestled in North Port. Updated 2 Bed / 1 Bath.

16. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (819 reviews)
"loved it here"
United States
Hannah
The price is NZ$557
includes taxes & fees
8 Sept - 9 Sept
Bridgewalk Resort

17. Lovers Key Resort 803 Stunning views of Estero Bay

Lovers Key Resort 803 Stunning views of Estero Bay
Fort Myers Beach
10.0 out of 10, Exceptional, (62 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$633
includes taxes & fees
12 Sept - 13 Sept
Lovers Key Resort 803 Stunning views of Estero Bay

18. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is NZ$659
includes taxes & fees
7 Sept - 8 Sept
MALU LANI Inn & Marina

19. 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, (471 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is NZ$294
includes taxes & fees
26 Aug - 27 Aug
Haley's at The Anna Maria Island Inn

20. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,757 reviews)
"Clean quiet and close to the beach. Best place for a quiet weekend getaway in a cute quiet beach town"
United States
Lindy
The price is NZ$305
includes taxes & fees
18 Aug - 19 Aug
Tropical Beach Resorts
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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