Search Southwest Florida Cottage Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southwest Florida cottages

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (193 reviews)
"Great place to stay! "
United States
Carlos
The price is ¥40,622
¥54,659 total
includes taxes & fees
Jan 21 - Jan 22
The Inn On Siesta Key
3.0 star property
The price is ¥14,547
¥67,449 total
includes taxes & fees
Jan 20 - Jan 21
Pet-friendly Home: 10 Mi to Lake Okeechobee!
9.2 out of 10, Wonderful, (12 reviews)
"Property was perfect for the price."
United States
William M.
The price is ¥11,068
¥26,390 total
includes taxes & fees
Jan 19 - Jan 20
Charming cottage for 2 across warm mineral springs park
9.8 out of 10, Exceptional, (79 reviews)
"A relaxing and magical place for your escape and mental peace. The place was excellent, and the check-in process was magnificent, with excellent communication from the host. This place is a paradise to clear your mind. Thank you so much for all the attention, Kevin, Lorena and Lilo "
United States
Kevin D.
The price is ¥21,204
¥40,782 total
includes taxes & fees
Jan 19 - Jan 20
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
9.6 out of 10, Exceptional, (5 reviews)
"Is good , and Beauty"
United States
Jorge T.
The price is ¥19,449
¥40,941 total
includes taxes & fees
Jan 19 - Jan 20
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
9.2 out of 10, Wonderful, (11 reviews)
"The place is so cute. Very convienent to Warm Mineral Spring. Make sure you go to $20 For non-resident. We had issue with coffeemaker and she was over immediately and fixed! Very ice lady! Washer and dryer outside in shed was convenient too! Bed was comfy too. Definitely would stay again and recommend!"
United States
Melissa
#3 Small house walking distance to Warm Mineral Spring
The price is ¥9,361
¥16,956 total
includes taxes & fees
Feb 1 - Feb 2
1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
10.0 out of 10, Exceptional, (3 reviews)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is ¥13,440
¥43,956 total
includes taxes & fees
Jan 26 - Jan 27
7mi to Anna Maria Newly Renovated Private Cottage

Cottage in Sunny Shores

The "Grouper"
9.4 out of 10, Exceptional, (45 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is ¥15,654
¥33,359 total
includes taxes & fees
Feb 7 - Feb 8
The "Grouper"
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is ¥23,718
¥54,354 total
includes taxes & fees
Jan 19 - Jan 20
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
10.0 out of 10, Exceptional, (1 review)
"Close enough to the beach to enjoy the area. The place was clean and had the necessities."
Singapore
Elizabeth M.
The price is ¥21,188
¥43,039 total
includes taxes & fees
Jan 19 - Jan 20
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4
3.0 star property
The price is ¥18,184
¥76,265 total
includes taxes & fees
Feb 8 - Feb 9
3 Mi to Downtown Bradenton: Family Home w/ Yard!
10.0 out of 10, Exceptional, (3 reviews)
"We stayed over kids spring break. Great location- not far from beaches and great restaurants. "
United States
Molly B.
The price is ¥23,244
¥48,273 total
includes taxes & fees
Jan 20 - Jan 21
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
9.0 out of 10, Wonderful, (11 reviews)
"The location and the property were both ideal for our getaway. "
United States
Trent
The price is ¥14,231
¥32,254 total
includes taxes & fees
Jan 19 - Jan 20
Studio#1-Back Bay Sunsets in Matlacha

Cottage in Manasota Beach

Cozy Beach Cottage
9.4 out of 10, Exceptional, (24 reviews)
"Wonderful location for a peaceful getaway "
United States
pamela
The price is ¥29,727
¥75,968 total
includes taxes & fees
Feb 7 - Feb 8
Cozy Beach Cottage
10.0 out of 10, Exceptional, (9 reviews)
"The home & location were both excellent. The surroundings were very quiet.We enjoyed our stay immensely and would definitely stay again.Thank you for a great experience!"
United States
debbra f.
The price is ¥22,611
¥44,941 total
includes taxes & fees
Jan 21 - Jan 22
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
9.8 out of 10, Exceptional, (9 reviews)
"Lovely old Florida area!! Quiet, charming area.Close to great restaurants, beaches, sunset!We will be back"
United States
Anonymous traveler
The price is ¥21,030
¥45,646 total
includes taxes & fees
Jan 19 - Jan 20
Old Florida Fishing Cottage See The Water From Living Room on Imperial River
9.2 out of 10, Wonderful, (5 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is ¥20,872
¥49,334 total
includes taxes & fees
Jan 19 - Jan 20
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.4 out of 10, Exceptional, (110 reviews)
"A true hidden gem on a great stretch of beach. Loved my time there and would recommend it. "
United States
John V.
The price is ¥47,120
¥90,372 total
includes taxes & fees
Feb 17 - Feb 18
Casey Key Beachfront Escape: Charming 1BR Cottage
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Charming property, clean, quiet."
United States
Nathan H.
The price is ¥26,090
¥31,993 total
includes taxes & fees
Jan 19 - Jan 20
Historic French Cottage in Downtown Arcadia
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Florida Hotel Reviews

Find out more about Southwest Florida

Southwest Florida Cottages information

Number of reviews
511
Accommodation
62 Cottages
Lowest Price
¥26,390
Highest Price
¥90,372

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between ¥26,390 and ¥90,372 per night. No matter your budget, you're sure to find an ideal place to soak up nature's beauty. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southwest Florida?
Southwest Florida has 62 cottages to choose from. Enter your dates and destination and start planning your perfect stay today.
Why book your cottage in Southwest Florida with Expedia?
We think that vacations should be stress-free, so if you're searching for cottages in Southwest Florida at the perfect price, Expedia can help. Keep the budget in check and pick a low-cost option far away from the city rush, or book a luxury cottage to pamper your loved ones.
How can I find cheap cottages in Southwest Florida?
With Expedia's useful filter tool, scoring cheap cottages in Southwest Florida is a cinch. To view properties that are friendly on the wallet, narrow down your search by amenities, star rating and budget.
What is there to do in Southwest Florida near my cottage?
Whether you're into shopping, dining, history or culture, Southwest Florida is one place where it's difficult to be bored! The leading city of Tampa has loads of attractions, including Henry B. Plant Museum, Orpheum Theater and David A. Straz Jr. Center for the Performing Arts. If you're taking off to Sarasota, Sarasota BayWalk, Ed Smith Stadium and Robert L. Taylor Community Complex shouldn't be missed.

Explore a world of travel with Expedia