Southwest Florida Cottages ￥7,924

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Our top choices for Southwest Florida cottages

A two-story house with a brick driveway leading to a front door, surrounded by various plants and trees.

1. The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

East End

Trina S.

￥56,602 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a green exterior, a blue door, and orange trim.

2. The "Grouper"

Sunny Shores

Canyon L.

￥32,326 total

includes taxes & fees

Nov 10 - Nov 11

A small, single-story building with a gray exterior, a white door, and a window with shutters.

3. Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

VIKTOR M.

￥21,601 total

includes taxes & fees

Nov 13 - Nov 14

A single-story building with a beige exterior and a red door.

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

East End

Stephen

￥44,835 total

includes taxes & fees

Nov 16 - Nov 17

A covered outdoor area with a hammock, wooden deck, and string lights.

5. Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

LaBelle

Jacob S.

￥41,394 total

includes taxes & fees

Nov 9 - Nov 10

A modern house with a covered outdoor area, a swimming pool, and a well-maintained lawn.

6. 2 Mi to Six Mile Preserve! Family Getaway w/ Pool

Fort Myers

￥75,301 total

includes taxes & fees

Nov 23 - Nov 24

A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

7. Cozy Private Cottage, Minutes to Anna Maria Island

Bradenton

Ismael

￥38,689 total

includes taxes & fees

Nov 10 - Nov 11

A bathroom with a toilet, sink, and mirror.

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

East End

Eric W.

￥46,896 total

includes taxes & fees

Nov 9 - Nov 10

A wooden deck with chairs and tables overlooking a body of water, surrounded by trees and greenery.

9. Peaceful Cute Cottage 1.5Mi to Beach Shared Dock on Imperial River Launch MAN

Bonita Shores

Rykadin

￥30,845 total

includes taxes & fees

Nov 9 - Nov 10

A covered outdoor seating area with wicker chairs and a table, overlooking a residential street with houses and palm trees.

10. Peaceful 1 Bed 1 Bath Cottage On Imperial River W Dock W&D Kitchen King Bed STF

Bonita Shores

Sean B.

￥30,845 total

includes taxes & fees

Nov 9 - Nov 10

11. Spacious Cottage Close To Beach 1.5 Mi On Park Like Gulf Access River W Dock ST

Bonita Shores

Ty B.

￥36,463 total

includes taxes & fees

Nov 12 - Nov 13

12. Updated 1BD/1BTH King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach SDD

Bonita Shores

Elizabeth M.

￥30,845 total

includes taxes & fees

Nov 9 - Nov 10

A hot tub with water bubbling, a life ring on the door, and a sign prohibiting chemicals.

13. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

Bokeelia

Lisa E.

￥33,869 total

includes taxes & fees

Nov 9 - Nov 10

A wooden deck with benches, surrounded by palm trees and a body of water, with a caution sign visible.

14. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

West End

Catherine B.

￥62,539 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

15. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

￥55,359 total

includes taxes & fees

Nov 9 - Nov 10

A house with a gravel driveway leading to a blue building with a porch.

16. Beach Days & Backyard Nights! Fort Myers Retreat

Harlem Heights

￥53,222 total

includes taxes & fees

Nov 23 - Nov 24

17. Old Florida Fishing Cottage See The Imperial River From Living Room IGN

Bonita Shores

Travis W.

￥34,008 total

includes taxes & fees

Nov 9 - Nov 10

18. Lovely Cottage 1.5 Mi Beach King Bed Full Kitchen Property Has Dock On River DLP

Bonita Shores

Mitchell K.

￥34,185 total

includes taxes & fees

Nov 12 - Nov 13

A yellow house with a porch, a mailbox, and a number 5306 on the door.

19. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

￥73,603 total

includes taxes & fees

Nov 9 - Nov 10

A garage with a metal gate and a driveway leading to a house.

20. Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!

Jacarandas

Kari M.

￥30,834 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Learn more about Southwest Florida

Amazing beaches, golf courses, and popular sights from Key West Express to Siesta Key Beach—explore Southwest Florida, a destination also known for its island views.

See all hotels in Southwest Florida

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Top reviews in Southwest Florida

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

The Inn On Siesta Key

Siesta Key

10/10 Excellent

We just finished our fall break getaway at The Inn On Siesta Key, and we absolutely loved it! The owners are so friendly and accommodating, staying here was the best choice we could have made. We stayed in the Cottage, and it was awesome, so inviting and cozy, and perfect for our family of 4. The great service started on our check in day. We arrived very early, as we had taken an early morning flight into Sarasota. Paige gave us an introduction to the property and let us change in the Cottage,...

Steven

A patio with two blue lounge chairs, a potted plant, and a gravel area.

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Bradenton

10/10 Excellent

My wife and I were with another couple on a birthday celebration and needed a place near Palma Sol Bay where we had reservations to ride the horses in the water. The location turned out to be perfect in all respects as it offered alternative options to get to specific locations throughout the area and it was within 30 minutes of everything even if traffic was heavy. The place was very clean and offered a small kitchen, two full bathrooms and two bedrooms (one queen, one king) and two couches...

Jeffrey

A single-story building with a sloped roof, a garage, and a covered outdoor area.

Summer-ready North Port Home w/ Private Pool!

North Port

10/10 Excellent

Gina

A single-story house with a front porch, a small deck, and a garage.

Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

8/10 Good

The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money.

Eleuterio

A turquoise house with a garage, a front yard with a small garden, and a driveway.

Largo Family Oasis: Private Pool & Hot Tub!

Harbor Bluffs

10/10 Excellent

Brian

A single-story house with a red door, a small front porch, and a clear driveway leading to the entrance.

Cozy St Pete Home ~ 2 Mi to Madeira Beach!

Bay Pines

10/10 Excellent

HELEN

A two-story house with a garage, a front porch with columns, and a brick facade.

Heated Pool + Game Room! Seminole Family Getaway

Seminole

10/10 Excellent

Deepak

Frequently Asked Questions

How much do cottages in Southwest Florida cost?

Prices for cottages in Southwest Florida range between ￥7,924 and ￥27,892 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 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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Search Southwest Florida Cottage Rentals

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Southwest Florida cottages

1. The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

2. The "Grouper"

3. Charming cottage for 2 across warm mineral springs park

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

5. Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

6. 2 Mi to Six Mile Preserve! Family Getaway w/ Pool

7. Cozy Private Cottage, Minutes to Anna Maria Island

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

9. Peaceful Cute Cottage 1.5Mi to Beach Shared Dock on Imperial River Launch MAN

10. Peaceful 1 Bed 1 Bath Cottage On Imperial River W Dock W&D Kitchen King Bed STF

11. Spacious Cottage Close To Beach 1.5 Mi On Park Like Gulf Access River W Dock ST

12. Updated 1BD/1BTH King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach SDD

13. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

14. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

15. Beach Tree Cottage,Walk To Beach& Siesta

16. Beach Days & Backyard Nights! Fort Myers Retreat

17. Old Florida Fishing Cottage See The Imperial River From Living Room IGN

18. Lovely Cottage 1.5 Mi Beach King Bed Full Kitchen Property Has Dock On River DLP

19. Yellow Palm Cottage, Heart of Siesta Key

20. Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!

Learn more about Southwest Florida

Top reviews in Southwest Florida

The Inn On Siesta Key

10/10 Excellent

Frequently Asked Questions

How much do cottages in Southwest Florida cost?

How many cottages are there in Southwest Florida?

Why book your cottage in Southwest Florida with Expedia?

How can I find cheap cottages in Southwest Florida?

What is there to do in Southwest Florida near my cottage?

Explore a world of travel with Expedia