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Check prices for these dates

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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Cottages in Southwest Florida

The Inn On Siesta Key
Enjoy the serene view from this balcony with a wicker chair and table.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The price is AU$472
includes taxes & fees
27 July - 28 July
The Inn On Siesta Key
Tropical Paradise On The Beach Permit VRC17-000168
Enjoy the ocean view from the deck, with access to the beach via a paved pathway.

Tropical Paradise On The Beach Permit VRC17-000168

9.4 out of 10, Exceptional, (133)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Terrace/patio

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (133)
"Our stay was great. Everything was as advertised and expected. "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Guests can park their golf cart at the charging station near the building with a green roof.

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (271)
"So many great features at this house in Bean Point including great access to the beach, Pine Street and a pool area that has it all. Thank you Dan and Lori for a wonderful stay!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Charming cottage in quiet area, close to beach & bay.
Guests can enjoy a porch with a sliding glass door leading to a cozy room.

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

9.8 out of 10, Exceptional, (279)
"This house was perfect! Close to the beach and restaurants. It had everything we needed. The fenced in backyard was great for our dog. We would definitely stay here again. "
Charming cottage in quiet area, close to beach & bay.
The "Grouper"
Stylish single-story home with a vibrant exterior, featuring a turquoise front door and a small garden area.

The "Grouper"

9.6 out of 10, Exceptional, (30)
"My stay was absolutely wonderful! The location is great, very convenient. The place itself is extremely comfortable, cozy, and it had everything we needed. The hosts were kind and attentive. It was truly worth every minute."
The price is AU$329
includes taxes & fees
31 July - 1 Aug
The "Grouper"
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
Guest laundry facility and storage area surrounded by lush greenery.

Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!

9.6 out of 10, Exceptional, (43)
"Proximity to things to do on the island was great!"
The price is AU$420
includes taxes & fees
4 Aug - 5 Aug
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is AU$793
includes taxes & fees
20 Aug - 21 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Guests enter through a glass door with wooden shutters, surrounded by lush greenery and a small garden.

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

9.6 out of 10, Exceptional, (44)
"Great place "
The price is AU$409
includes taxes & fees
3 Aug - 4 Aug
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Relax on the patio with a comfortable bench and wicker sofa, surrounded by a peaceful atmosphere.

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"We were extremely happy with our stay and Evan as our host. He went out of his way to make sure everything went smoothly including helping us find all the beach amenities. The house was excellent and just what we needed, just a short walk across the road to the beach. We would definitely stay here again!"
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Country Cottage Home
Relax in a serene outdoor space surrounded by a tropical mural and lush greenery.

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Loved our stay at the property. Would book it again!"
Country Cottage Home
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Relax in the serene outdoor seating area surrounded by lush greenery and a charming brick patio.

The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.

9.8 out of 10, Exceptional, (10)
"nice place great location, we will stay there again"
The price is AU$745
includes taxes & fees
26 July - 27 July
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Moninanu - Modern Wooded Cottage in North Naples
Stroll through the beautifully landscaped front yard, featuring a variety of plants and trees, to the entrance of Moninanu Cottage.

Moninanu - Modern Wooded Cottage in North Naples

10.0 out of 10, Exceptional, (11)
"A great place for us to stay so we can be close to family"
Moninanu - Modern Wooded Cottage in North Naples
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Enjoy cooking in this well-equipped kitchen with an oven, coffee maker, and ample counter space.

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

9.2 out of 10, Wonderful, (63)
"Had a lovely stay.. close to beach and Food. "
The price is AU$414
includes taxes & fees
9 Aug - 10 Aug
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views
Outdoor dining

West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views

9.8 out of 10, Exceptional, (16)
"Great property, very clean and comfortable! The pond in the backyard and wildlife was beautiful. Hosts were very responsive and accommodating!"
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Enjoy a serene beachfront retreat surrounded by lush greenery and a tranquil ocean view.

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (89)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Across The Street From #1 Beach
Residential property with a two-story building, driveway, patio, and pool area surrounded by palm trees and greenery.

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Situated on a sandy beach, this property offers a beachfront location with lush greenery and a seating area.

Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

9.6 out of 10, Exceptional, (21)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Residential area with modern homes and apartment buildings surrounded by lush greenery and palm trees.

Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

8.8 out of 10, Excellent, (8)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lots of beach time"
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Enjoy dining or relaxing on the covered porch with a glass table and wicker chairs.

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

9.6 out of 10, Exceptional, (79)
"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
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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Frequently asked questions

How much do cottages in Southwest Florida cost?
You'll pay between AU$329 and AU$793 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 58 cottages in Southwest Florida and then book your favourite. Whether you're dreaming of a holiday with the fam or a break with buddies, your perfect stay is just a few clicks away with Expedia.
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 Theatre 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.