Search Cottages in Southwest Florida

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Compare 21 Cottages in Southwest Florida with updated reviews, rates, and availability.

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
New screened Florida Room-for relaxing alone or together outside sans bugs!

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

10.0 out of 10, Exceptional, (62)
"Flamingo Cottage offers everything a Florida getaway has to offer. Gracious owners; a lovely, well appointed vintage beach house and a perfect quiet location for an stress-free vacation. We look forward to our return next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Adorable Guest house with 2 bedrooms-Great Location
Terrace/patio

Adorable Guest house with 2 bedrooms-Great Location

9.6 out of 10, Exceptional, (52)
"Everything was so sweet and very well put together! It was myself and 2 sons for a baseball tournament and Rolando was AMAZING!"
Adorable Guest house with 2 bedrooms-Great Location
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
Don't miss a sunset! Experience Lido's sunset as the sun dips below the Gulf!

Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!

10.0 out of 10, Exceptional, (79)
"We loved our cottage. Perfect location very private but not isolated. Clean and comfortable. We will definitely return next year. We had all the convenience of home."
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Charming Guesthouse

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

10.0 out of 10, Exceptional, (104)
"The place was great!!! Kathy and Jerry are excellent hosts!!! They even invited us for thanksgiving dinner with their family and friends! Very relaxing time!!!"
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Your own privet spa!! cleaned and sanitized after every guest!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

9.6 out of 10, Exceptional, (7)
"Our family stayed at La Mia Casa, the listing of the rental was accurate so we weren’t surprised by anything. The host does a WONDERFUL job of providing any and everything you might need while you stay. The proximity to the beach and points of interest is great it never took us more than 10-15mins to go to the beach or eateries. Our host even extended our checkout which I thought was very nice."
The price is AED 477
AED 1,236 total
includes taxes & fees
5 Jan - 6 January 2025
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm
living room area/ceiling fans throughout home

Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm

9.8 out of 10, Exceptional, (13)
"We stayed for about one month for work. The area is nice a quiet. The cottage is comfortable and convenient to local retail and restaurants. I'd recommend to others."
Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm
Charming cottage in quiet area, close to beach & bay.

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (252)
"Stayed there again for a few days for our anniversary. Great location, nice place, wonderful host. We couldn't ask for anything better. That's why we keep going back. We left just before Hurricane Helene and are praying for Cindy and Anna Maria Island. "
Charming cottage in quiet area, close to beach & bay.
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Unassuming exterior belies the roomy interior with 4 bedrooms 3 baths and a pool

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (110)
"Great family house. Management is excellent."
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Cozy livingroom.

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

9.8 out of 10, Exceptional, (69)
"This little cottage is a great location right near the beach. We enjoyed walking down to Bean Point at sunrise and seeing all the snook in the surf. The beach near the cottage is perfect for the kids since it is very shallow and gradual."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Absolutely breathtaking sunsets on the beach!

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (181)
"Everything was great only thing it needed to have was a tv in the master bedroom "
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Private 2 Bedroom Cottage Close to Everything for Florida Fun.
Outdoor dining

Private 2 Bedroom Cottage Close to Everything for Florida Fun.

10.0 out of 10, Exceptional, (8)
"This place was amazing. It even offers more than the listing describes because we were unaware of how big the grounds were! The kids had plenty of room to roam and explore safely. The beds were extremely comfortable. The place has original art which is amazing to look at! The location is perfect for privacy but also clise to the the beaches and the historic district. This will become our new yearly family spot. Got to meet Carrol as we unfortunately had to leave and she is fantastic! We havent...
Private 2 Bedroom Cottage Close to Everything for Florida Fun.
Blue Water Retreat @ Vanderbilt- steps to beaches/shopping/dining/entertainment!
Living area

Blue Water Retreat @ Vanderbilt- steps to beaches/shopping/dining/entertainment!

10.0 out of 10, Exceptional, (2)
"The inside looks newly renovated. Furnishings, linens, towels, very new. Everything we needed for the kitchen. Great beach chairs was a bonus! Perfect for a couple or family of 4. Can walk for dining, shopping and beach. (1 to 1-1/2 miles). Photos in add very accurate."
Blue Water Retreat @ Vanderbilt- steps to beaches/shopping/dining/entertainment!
Keys stilt cottage lower unit
modern bathroom

Keys stilt cottage lower unit

9.4 out of 10, Exceptional, (29)
"spacious, very clean & comfortable cottage. Owner & staff were hands-on & helpful. Loved our stay!!!"
Keys stilt cottage lower unit
fabulous waterfront resort, 3 pools, lazy river, walk to 5th Ave!
zero entry beach pool

fabulous waterfront resort, 3 pools, lazy river, walk to 5th Ave!

10.0 out of 10, Exceptional, (28)
"Excellent location, very comfortable, only issue was the hurricane 😪"
fabulous waterfront resort, 3 pools, lazy river, walk to 5th Ave!
Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
Exterior

Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.

9.6 out of 10, Exceptional, (5)
"Great location with many Naples activities nearby. Very relaxing and clean with all needed amenities."
Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
3 Pools, lazy river, walk to 5th ave restaurants!
Relax, 3 pools and your very own lazy river

3 Pools, lazy river, walk to 5th ave restaurants!

9.8 out of 10, Exceptional, (106)
"Great stay in this two bedroom unit at Marco Bay Club! Alan (manager/owner) was extremely flexible and considerate with our dates, which needed to be moved due to tropical storm. Upgraded unit with contemporary finishes and all conveniences of upscale hotel. Will surely be back there soon."
3 Pools, lazy river, walk to 5th ave restaurants!
Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
Living area

Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!

9.4 out of 10, Exceptional, (30)
"We usually visit Destin, this summer we skipped planning my sons wedding in October. After the tragic and very unexpected death of our son 55 days before his wedding, we chose to come further south feom Texas to heal, celebrate 26 years of marriage and relax. The house was what we needed, plus for a family ready to prepare meals. We hope to bring our adult kids and daughter in love this direction for a change of scenery. We will not have a problem coming back to stay at this location. We...
Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
Tropical Port Charlotte Cottage - Walk to Bay!
Port Charlotte Vacation Rental | 1BR | 1BA | 800 Sq Ft | 2 Steps Required

Tropical Port Charlotte Cottage - Walk to Bay!

7.8 out of 10, Good, (11)
"The heater/ac didn't work. The contact brought over 2 space heaters. The front blinds were missing the cord. The bed was soft. We liked the location close to the Bay park."
Tropical Port Charlotte Cottage - Walk to Bay!
Fort Myers Home, Lanai & Private, Heated Pool
Pool

Fort Myers Home, Lanai & Private, Heated Pool

3.0 star property
Fort Myers Home, Lanai & Private, Heated Pool
Vacation Home Near the Beach!
Living area

Vacation Home Near the Beach!

10.0 out of 10, Exceptional, (16)
"We stayed at this house for a friends wedding weekend. The house was great and we used the beach gear on our beach day. Would definitely recommend."
The price is AED 367
AED 1,782 total
includes taxes & fees
31 Jan - 1 February 2025
Vacation Home Near the Beach!
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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Other property types in Southwest Florida

The Suites at Fishermen’s Village- 2 Bedroom Suites
Exterior

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (699)
"Very enjoyable stay!"
The price is AED 1,093
AED 1,224 total
includes taxes & fees
12 Jan - 13 January 2025
The Suites at Fishermen’s Village- 2 Bedroom Suites
Bellasera Resort
Outdoor pool

Bellasera Resort

4.0 star property
9.6 out of 10, Exceptional, (2075)
"Great location great day"
The price is AED 1,723
AED 2,014 total
includes taxes & fees
8 Jan - 9 January 2025
Bellasera Resort
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Exterior

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4.0 star property
9.2 out of 10, Wonderful, (490)
"This property is incredible. We had such a wonderful stay. The room was phenomenal. The facilities were beyond wonderful. Our family had a great trip "
The price is AED 922
AED 1,130 total
includes taxes & fees
14 Jan - 15 January 2025
Hyatt Vacation Club at Coconut Cove, Bonita Springs
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.

Frequently asked questions

How much do cottages in Southwest Florida cost?
Rates for cottages in Southwest Florida range between AED 367 and AED 477 per night. No matter your budget, you’re sure to find a perfect place to immerse yourself in nature. 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?
You can choose from 21 cottages in Southwest Florida. Whether you’re traveling with the entire family, as a table-for-two or with a group of pals, Expedia makes it easy to find an ideal place.
Why book your cottage in Southwest Florida with Expedia?
Reserving a cottage in Southwest Florida is as easy as clicking on your travel dates and choosing an ideal place for a vacation in nature. From ritzy retreats to low-cost stays and cottages that come with amenities like a kitchenette, Expedia has something for all tastes. As for terrific deals? We’ve have them as well!
How can I find cheap cottages in Southwest Florida?
With Expedia’s helpful filter tool, comparing cheap cottages in Southwest Florida has never been simpler. To discover accommodations that’ll make your bank balance smile, narrow down your search by amenities, budget and star rating.