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Compare 39 Cottages in Southwest Florida with updated reviews, rates, and availability.

Charming cottage in quiet area, close to beach & bay.
9.8 out of 10, Exceptional, (238)
"Had a great stay, was only there for 2 nights, wish we could have stayed more. Home very clean, stocked with everything you would need. Great location, short walk to beach, pier and many places to eat. Free trolley stop is down the block and a great way to get around the island. Hoping to come back and stay again."
Charming cottage in quiet area, close to beach & bay.
Modern, Spacious, 2BR Cottage, Private Beach Access, Dog Friendly, Full Kitchen!
9.6 out of 10, Exceptional, (52)
"This property is wonderful. It is close to the beach and everything is there that you need. You can always get ahold of the owner if you ever need anyrhing. We have stayed there the last 2 years and the place is always so clean when we arrive. I highly recommend this place."
Modern, Spacious, 2BR Cottage, Private Beach Access, Dog Friendly, Full Kitchen!
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
9.0 out of 10, Wonderful, (39)
"Beautiful peaceful place!!"
The price is $169
$297 total
includes taxes & fees
Jul 6 - Jul 7
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
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Adorable and Modern 1 Bedroom, Private Beach Access, Dog Friendly, Full Kitchen
9.2 out of 10, Wonderful, (54)
"We had a wonderful stay! This is our, go to, place to stay when visiting family in Englewood. A short walk to the beach. Beautiful sunsets! Close to everything and very laid back and relaxing. Our Host Rikki is alsways outstanding and communications are exceptional! Everything is top notch and the unit is always spotless upon arrival. Never disappointed!"
Adorable and Modern 1 Bedroom, Private Beach Access, Dog Friendly, Full Kitchen
Beachfront Cottage, Best location on Manasota Key, Sleeps 4, Kayaks and Wi-Fi
10.0 out of 10, Exceptional, (120)
"Just what we were looking for to get away from all the hustle. Very private house loaded directly on the beach, beautiful sunsets. This is our second time stating here which means we like a bunch. Everything we need to getaway and relax."
Beachfront Cottage, Best location on Manasota Key, Sleeps 4, Kayaks and Wi-Fi
Historic Bradenton Cottage ~ 1 Mi to Downtown
10.0 out of 10, Exceptional, (23)
"We were seeking a place to stay for a family matter that came upon us suddenly. The Cottage was delightful. Two very nice bedrooms, lovely bath and functional kitchen. The living room was large and comfortable. The house is tastefully decorated and the mattresses are comfortable. George, the owner, stayed in touch and even after wel left"
Historic Bradenton Cottage ~ 1 Mi to Downtown
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
9.6 out of 10, Exceptional, (42)
"Everything was great! Except for the no-see-ems that came out in the evenings. Those bitting little bugs are awful! Bring bug spray or buy some at one of the local shops. The people were friendly. The neighborhood was safe. The food was amazing. Our fav for breakfast was Lighthouse Cafe (especially the mimosas and eggs Benedict). For supper we loved Wickies, Tutti Pazzi and Doc Fords. We never tried Mudbugs, but it looked inviting. We just ran out of time. Doc Fords was the longest bike ride we...
The price is $179
$309 total
includes taxes & fees
Jun 17 - Jun 18
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
9.8 out of 10, Exceptional, (67)
"My friend and I, to celebrate Mother's Day without kids, spend 4 days at this delightful cottage on Anna Maria Island. I have only glowing reports regarding the location and the hosts. This cute and old-fashioned cottage sits in a great location and is in walking distance to shops, the Anna Maria Pier, restaurants and especially, the beach! It sits next to Capt Anthony's fish market which would have been interesting to watch; however, the owners were on vacation so we missed the action. Joanne...
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
3 Pools, lazy river, walk to 5th ave restaurants!
9.8 out of 10, Exceptional, (100)
"Good"
3 Pools, lazy river, walk to 5th ave restaurants!
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
10.0 out of 10, Exceptional, (74)
"We had a wonderful week in paradise!"
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
9.8 out of 10, Exceptional, (30)
"The room was amazing but the bed was to firm with flat pillows. Would return but bring our own pillows. Clean snd had lots of amenities "
The price is $179
$301 total
includes taxes & fees
Jun 22 - Jun 23
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
9.6 out of 10, Exceptional, (36)
"Nicely located close to the beach & a super ice cream shop! The next door plaza also had the best shopping we found on the Island. Our accommodations exceeded expectations with nice wine glasses,dishware,beach chairs & even a Kurig Coffee Maker. The beach towels seemed new"
The price is $199
$376 total
includes taxes & fees
Jun 17 - Jun 18
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Keys stilt cottage lower unit
9.6 out of 10, Exceptional, (27)
"I had a great time at this very well appointed property. Close to restaurants, Tin City, grocery stores, etc. Communication with Carlos was seamless. Would definitely recommend and will be back. Thank you!!"
The price is $79
$249 total
includes taxes & fees
Jul 7 - Jul 8
Keys stilt cottage lower unit
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
9.8 out of 10, Exceptional, (32)
"Title: Relaxing Getaway with Private Beach Access I recently stayed this property that exceeded all my expectations. The property, was immaculately clean and provided a quiet and peaceful retreat. One of the highlights of the rental was the access to a private beach at the end of the road, which offered a serene and secluded spot to unwind and enjoy the sun and sunsets. Additionally, the inclusion of free bikes added an extra layer of enjoyment to the stay. Exploring the surrounding area on...
The price is $229
$463 total
includes taxes & fees
Jun 23 - Jun 24
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
9.4 out of 10, Exceptional, (85)
"Walked on beach and collected shells. It was very nice and relaxing. Had the best sleep her than I have had in a long time. Nice people ont he island"
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
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, (103)
"Great location. Great home. Pictures don’t do it justice - family that arrived before us called while we were a few miles out and said to go ahead get ready to be surprised. My in-laws rented the property next door which was super convenient for our large family and we had plenty of room. It made for a trip we won’t forget. So much fun. Being able to walk to St Armands Circle was the icing on the cake. Beautiful beach, pool, amenities..too much to list. We look forward to booking this property...
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
9.4 out of 10, Exceptional, (172)
"Came here for a girls trip and absolutely loved it! The host was fantastic, the location was just minutes from the beach and I can’t wait to rebook! The location was clean and filled with all of the things you’ll need. The guestbook was filled with all kinds of information, places to visit and places to eat! Messaged the host a few times and she always got right back to me. I was very pleased with our stay and would highly recommend staying here! (:"
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
8.8 out of 10, Excellent, (5)
"Best location on the island. Cottage is exactly what you want to find at the beach. This is my second of many more to come."
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
9.6 out of 10, Exceptional, (35)
"The house was very cute. Location of this house couldn’t have been better. Super close to restaurants, pier, shopping and the beach. Love the vibe of riding bikes or golf carts to get around. Outside seating area of the house front and back was nice. Definitely would rent again."
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
The Rosella-Great value on Sanibel! Walk to dining, shops and The Lighthouse-on Historic East End!
9.4 out of 10, Exceptional, (19)
"awesome"
The price is $199
$330 total
includes taxes & fees
Jun 16 - Jun 17
The Rosella-Great value on Sanibel! Walk to dining, shops and The Lighthouse-on Historic East End!
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See all available properties in Southwest Florida
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.

Other property types in Southwest Florida

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (573)
"The room was wonderful, beautiful views of the bay and beach. However the floors were filthy. Management needs to hire a tile cleaning company to professionally clean the floors. The dust mop method used by the hotel staff does not work. If you walk aroung barefooted in the room your feet WILL become black."
The price is $149
$167 total
includes taxes & fees
Jun 23 - Jun 24
The Suites at Fishermen’s Village- 2 Bedroom Suites
Bellasera Resort
4.0 star property
9.6 out of 10, Exceptional, (1940)
"&#x1faf6;&#x1f3fb;❤️❤️❤️❤️"
The price is $263
$319 total
includes taxes & fees
Jun 16 - Jun 17
Bellasera Resort
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2011)
"Close to the beach. An older property, but very well maintained. "
The price is $141
$159 total
includes taxes & fees
Jun 16 - Jun 17
Hibiscus Suites - Gateway to Siesta Key
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.

Southwest Florida Cottages information

Number of reviews
1,294
Accommodation
39 Cottages
Lowest Price
$79
Highest Price
$229

Frequently asked questions

How much do cottages in Southwest Florida cost?
You’ll pay between $79 and $229 per night for cottages in Southwest Florida. Whatever your budget, a wonderful stay is only clicks away on Expedia. This price was 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?
Browse our 39 cottages in Southwest Florida and then book your favorite. Whether you’re dreaming of a vacation with the fam or a break with buddies, your perfect stay is just a few clicks away with Expedia.
Why book your cottage in Southwest Florida with Expedia?
Expedia has some terrific cottages in Southwest Florida, so start packing for a memorable stay on nature’s doorstep. If you’re sticking to a budget, click on how much you’re willing to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with a hot tub or free WiFi. We’ll help you find the right place whatever your plans or bank balance.
How can I find cheap cottages in Southwest Florida?
A great way to score cheap cottages in Southwest Florida is with Expedia’s handy filter tool. Refine your search by amenities, budget and star rating to take advantage of awesome bargains in a few clicks.
What is there to do in Southwest Florida near my cottage?
Whether you enjoy food, shopping, history or sightseeing, Southwest Florida offers it all, and more! The top city of Tampa has lots of things to see and do, including Florida Aquarium, Tampa Theater and Tampa Museum of Art. If you’re on your way to Naples, Naples Beach, Naples Zoo at Caribbean Gardens and Collier County Museum are worth putting on your itinerary.

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