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Our top choices for Southwest Florida cottages

House (2 Bedrooms) | Interior
Relax in Hot Tub, Walk to Springs: North Port Home

Cottage in North Port

Relax in Hot Tub, Walk to Springs: North Port Home
3.0 star property
Relax in Hot Tub, Walk to Springs: North Port Home
The Lookout, 1 King Bedroom 1 Bath | Terrace/patio
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is ￥41,112
￥55,192 total
includes taxes & fees
Dec 21 - Dec 22
The Inn On Siesta Key
Exterior
Charming cottage for 2 across warm mineral springs park

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is ￥11,670
￥26,849 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Charming cottage for 2 across warm mineral springs park
Exterior
#3 Small house walking distance to Warm Mineral Spring

Cottage in Warm Mineral Springs

#3 Small house walking distance to Warm Mineral Spring
9.0 out of 10, Wonderful, (9)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is ￥9,465
￥24,546 total
includes taxes & fees
Dec 29 - Dec 30
#3 Small house walking distance to Warm Mineral Spring
Property grounds
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

Cottage in West End

Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
9.0 out of 10, Wonderful, (23)
"Loved our stay at the cottage. It was a perfect getaway for 2. Short walk to a quiet beach. Convenient to restaurants and Ding Darling.We will be back!"
United States
Catherine B.
The price is ￥39,438
￥83,717 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Property grounds
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River

Cottage in Bonita Shores

Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
9.6 out of 10, Exceptional, (4)
"Is good , and Beauty"
United States
Jorge T.
The price is ￥20,823
￥42,744 total
includes taxes & fees
Dec 21 - Dec 22
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
Exterior
Studio#1-Back Bay Sunsets in Matlacha

Cottage in Matlacha

Studio#1-Back Bay Sunsets in Matlacha
9.0 out of 10, Wonderful, (11)
"The location and the property were both ideal for our getaway. "
United States
Trent
The price is ￥15,775
￥33,937 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Studio#1-Back Bay Sunsets in Matlacha
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

Cottage in Bradenton

7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (3)
"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 ￥18,772
￥50,229 total
includes taxes & fees
Jan 1 - Jan 2, 2026
7mi to Anna Maria Newly Renovated Private Cottage
Smart TV
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach

Cottage in Bonita Shores

Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
10.0 out of 10, Exceptional, (3)
"We stayed over kids spring break. Great location- not far from beaches and great restaurants. "
United States
Molly B.
The price is ￥22,558
￥47,613 total
includes taxes & fees
Dec 21 - Dec 22
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
Exterior
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

Cottage in LaBelle

Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
9.8 out of 10, Exceptional, (77)
"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 ￥21,154
￥40,687 total
includes taxes & fees
Dec 21 - Dec 22
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
House (3 Bedrooms) | Interior
Pet-friendly Home: 10 Mi to Lake Okeechobee!

Cottage in Clewiston

Pet-friendly Home: 10 Mi to Lake Okeechobee!
3.0 star property
The price is ￥14,513
￥67,291 total
includes taxes & fees
Dec 28 - Dec 29
Pet-friendly Home: 10 Mi to Lake Okeechobee!
Property grounds
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!

Cottage in East End

Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
9.4 out of 10, Exceptional, (58)
"Great locationThe bikes were a great asset "
United States
Brian Z.
The price is ￥39,438
￥69,677 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
On the beach, sun loungers, beach towels
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Cottage in Casey Key

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
9.4 out of 10, Exceptional, (108)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
The price is ￥31,235
￥71,073 total
includes taxes & fees
Dec 25 - Dec 26
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Terrace/patio
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4

Cottage in Bonita Shores

Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
10.0 out of 10, Exceptional, (8)
"Loved the cabin feel. Spent most evenings by the river on the amazing deck. "
United States
Michele A.
The price is ￥24,451
￥47,104 total
includes taxes & fees
Dec 22 - Dec 23
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
Fridge, microwave, coffee/tea maker
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

Cottage in East End

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
9.2 out of 10, Wonderful, (70)
"This was a cute little cottage close to the beach. Wonderful lighthouse restaurant next door. Bikes were conveniently available for use."
United States
consuelo
The price is ￥39,438
￥70,624 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Smart TV
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4

Cottage in Bonita Shores

Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4
10.0 out of 10, Exceptional, (1)
"Close enough to the beach to enjoy the area. The place was clean and had the necessities."
Singapore
Elizabeth M.
The price is ￥22,401
￥44,661 total
includes taxes & fees
Dec 21 - Dec 22
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4
Exterior
The "Grouper"

Cottage in Sunny Shores

The "Grouper"
9.4 out of 10, Exceptional, (43)
"A beautiful little place to stay only minutes away from the beach! Very cozy and clean! "
United States
savana w.
The price is ￥15,617
￥33,280 total
includes taxes & fees
Dec 22 - Dec 23
The "Grouper"
Property grounds
Old Florida Fishing Cottage See The Water From Living Room on Imperial River

Cottage in Bonita Shores

Old Florida Fishing Cottage See The Water From Living Room on Imperial River
9.8 out of 10, Exceptional, (9)
"Hosts were responsive and addressed all questions in a timely manner. Would stay there again."
United States
Marie R.
The price is ￥23,663
￥47,426 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Old Florida Fishing Cottage See The Water From Living Room on Imperial River
Exterior
Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!

Cottage in Jacarandas

Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!
8.0 out of 10, Very Good, (1)
"Property was very clean. All essential items on the property worked fine. One missing item from the property and that was the space heater. Understandable considering there is normally not a huge call for such an item in FL! Owner/manager was responsive when contacted. Would not recommend this property for anyone with any mobility disabilities due to property layout. This property met my needs for a week visit(well close to a week) to my parents. For the price it worked just fine. ...
United States
Diane S.
The price is ￥14,056
￥32,901 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Cottage in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"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 ￥23,505
￥51,427 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"It’s ok"
Michael 3-night trip
Posted 1 day ago
Kompose Boutique Hotel

Find out more about Southwest Florida

Southwest Florida Cottages information

Number of reviews
628
Accommodation
62 Cottages
Lowest Price
￥24,546
Highest Price
￥83,717

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between ￥24,546 and ￥83,717 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.

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