A crowded beach with people sunbathing and swimming.

Southwest Florida Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southwest Florida vacation rentals

A modern hotel room with a kitchenette, a bed, a seating area, and a wardrobe.

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, (159 reviews)
"Great location, clean and comfortable"
United States
Jodi
$84 nightly
The price is $94
Oct 21 - Oct 22
Total with taxes and fees
StudioRes by Marriott Fort Myers Airport
A beach with a thatched-roof structure, palm trees, and a view of the sea.

2. 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, (1,344 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
$175 nightly
The price is $196
Oct 30 - Oct 31
Total with taxes and fees
The Suites at Fishermen’s Village
A balcony with wicker furniture, a bottle, and glasses, overlooking a sunset over a body of water and buildings.

3. Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,092 reviews)
"Clean room, AC was Perfect, and deck view was amazing"
United States
Carlos
$248 nightly
The price is $277
Oct 18 - Oct 19
Total with taxes and fees
Lovers Key Resort
A beach with a view of the ocean and a sunset.

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,162 reviews)
"Great location"
United States
Nicole
$247 nightly
The price is $276
Oct 17 - Oct 18
Total with taxes and fees
Island Inn
A pool area with a waterfall feature, lounge chairs, and palm trees.

5. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,973 reviews)
"Amazing resort,"
United States
kurt
$150 nightly
The price is $170
Oct 19 - Oct 20
Total with taxes and fees
Tropical Beach Resorts
A beach view from a balcony with a pool, palm trees, and a building with a balcony.

6. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,939 reviews)
"Great stay."
United States
Angie
$230 nightly
The price is $256
Oct 23 - Oct 24
Total with taxes and fees
Edison Beach House
A sectional sofa with a chaise, a small table, and a wicker ottoman in an outdoor setting with a clear sky and palm trees.

7. Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
8.0 out of 10, Very good, (1,026 reviews)
"Great location and cleanliness was excellent"
United States
J
$146 nightly
The price is $163
Nov 8 - Nov 9
Total with taxes and fees
Flamingo Inn
A modern living room with a white sofa, colorful cushions, a wooden coffee table, and a ceiling fan.

8. Park Shore Resort - Dream Holiday Stays

Park Shore Resort - Dream Holiday Stays
4.0 star property
Park Shore
$441 nightly
The price is $489
Nov 1 - Nov 2
Total with taxes and fees
Park Shore Resort - Dream Holiday Stays
A beach with clear turquoise water and a sandy shore.

9. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (76 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$191 nightly
The price is $213
Oct 18 - Oct 19
Total with taxes and fees
The "Grouper"
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

10. 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, (477 reviews)
"Great location and walking distance to the beach"
United States
Francesca
$200 nightly
The price is $226
Nov 2 - Nov 3
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
A beach with a clear sky, palm trees, and a sunlit ocean.

11. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (978 reviews)
"Highly recommended, coastal by the sea, good for family outings."
United States
MARYTE
$558 nightly
The price is $614
Oct 18 - Oct 19
Total with taxes and fees
GullWing Beach Resort
A pool area with lounge chairs and umbrellas, a beach with umbrellas and lounge chairs, and palm trees.

12. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,714 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
$416 nightly
The price is $464
Oct 18 - Oct 19
Total with taxes and fees
Sundial Beach Resort & Spa
A covered outdoor area with a hammock, wooden deck, and string lights.

13. 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.
$254 nightly
The price is $274
Oct 18 - Oct 19
Total with taxes and fees
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

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
$378 nightly
The price is $420
Oct 16 - Oct 17
Total with taxes and fees
Noel Real Estate
A compact room with a bed, a dining area with a table and chairs, a kitchen area, and a painting on the wall.

15. Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
East End
9.0 out of 10, Wonderful, (76 reviews)
"Great little place, really enjoyed having the kitchen and the grill. "
United States
Eric W.
$303 nightly
The price is $321
Oct 18 - Oct 19
Total with taxes and fees
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
A family of four holding hands on a sandy beach with a clear sky and calm sea in the background.

16. 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
$315 nightly
The price is $334
Oct 18 - Oct 19
Total with taxes and fees
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
A kitchen with a microwave, cabinets, and a ceiling fan. There is a dining area with a table and chairs.

17. 2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
3.0 star property
Naples
$187 nightly
The price is $208
Oct 17 - Oct 18
Total with taxes and fees
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
A modern living room with a large window, a flat-screen TV, and a potted plant.

18. 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.
$193 nightly
The price is $215
Oct 18 - Oct 19
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.
A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

19. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,342 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$345 nightly
The price is $383
Oct 21 - Oct 22
Total with taxes and fees
Bellasera Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

20. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (692 reviews)
"Enjoyed our stay"
United States
Robin
$205 nightly
The price is $231
Nov 4 - Nov 5
Total with taxes and fees
A Beach Retreat
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

Naples Bay Resort & Marina

Naples Bay Resort & Marina

10/10 Excellent
"Very clean and friendly staff"
Michelle 2-night trip
Posted 4 hours ago
Naples Bay Resort & Marina

Find out more about Southwest Florida

Everything you need to know about Southwest Florida vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Florida vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Florida vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southwest Florida in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $86 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southwest Florida rentals

At Expedia, we put the best Southwest Florida vacation 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 vacation.

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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