Southwest Orlando Cottages

Southwest Orlando Cottages
Florida
United States of America
Cottages
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Our top choices for Southwest Orlando cottages

A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

A house with a red door, a front porch, and a pathway leading to the entrance.

A room with a bed, a TV on a stand, a bookshelf, and a window with blinds.

A kitchen with a red brick wall, stainless steel appliances, and a wooden table.

1. Downtown Cottage

Downtown Cottage

Colonialtown North

8.8 out of 10, Excellent, (16 reviews)

8.8/10

Excellent

(16 reviews)

"Clean perfect location for what we needed "

Jerred B.

The price is €166

€166

includes taxes & fees

25 Oct - 26 Oct

Downtown Cottage

A serene landscape with a pond, trees with Spanish moss, and a palm tree.

A bathroom with a shower, a marble wall, a window with a plant, and a showerhead.

A living room with a grey sofa, a flat-screen TV, a sound system, and a wooden coffee table.

A house with a dark front door, a small porch with a bench, and a potted plant.

2. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Windermere

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is €300

€300

includes taxes & fees

18 Nov - 19 Nov

Shore Steps Cottage - Walking Distance To The Town Of Windermere

A white building with large windows and a brick pathway leading to it.

A living room with a black leather sofa, a white coffee table, and a potted plant. There is a ceiling fan, a TV, and a door leading to a balcony with outdoor furniture.

A living room with a black leather sofa, a patterned throw pillow, a wooden coffee table, and a colorful rug. There is a large window with blinds, a framed picture on the wall, and a potted plant.

A brick pathway leading to a building with white siding.

3. The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

College Park

10.0 out of 10, Exceptional, (55 reviews)

10/10

Exceptional

(55 reviews)

"Everything was super clean and exactly as described. Great location and great stay!"

Garrett S.

The price is €293

€293

includes taxes & fees

3 Nov - 4 Nov

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

A living room with a grey sectional sofa, yellow cushions, a round wicker coffee table, and a patterned rug. There are two windows with blinds, a ceiling fan, and a dining area with a table and chairs.

A modern kitchen with a built-in microwave, coffee maker, toaster, and a window with a view of trees.

A bedroom with a bed, a wardrobe, a sofa, and a lamp.

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Orlando

The price is €186

€186

includes taxes & fees

27 Oct - 28 Oct

Romantic Lakefront Getaway with Balcony near Downtown Orlando

A single-story mobile home with a front porch and a small deck.

A kitchen with a wooden table and stools, a gray couch, and a view of a residential area through a window.

A glass-enclosed shower with a marble floor, a towel rack, and a visible showerhead.

A modern kitchen with a refrigerator, stove, and microwave. There is a dining area with a table and chairs.

5. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~

Kissimmee

The price is €192

€192

includes taxes & fees

25 Oct - 26 Oct

Newly Remodeled Tiny Home 20 minutes from Disney!~

A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

A shower with a handheld showerhead and a wall-mounted control.

A modern kitchen with a large window, stainless steel appliances, and a sign that reads "Kitchen the heart of the home."

A living room with a brown leather sofa, a round metal coffee table with a vase of flowers, a wooden cabinet with a flat-screen TV, and a ceiling fan.

6. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Orlando

The price is €215

€215

includes taxes & fees

26 Oct - 27 Oct

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

A resort with multiple swimming pools, palm trees, and a large building in the background.

A resort with a large swimming pool, a water park, and a view of a lake.

A living room with two grey sofas, a wooden coffee table, and two side tables with lamps.

An outdoor patio area with a covered seating area, a water feature, and lush greenery.

7. Th10 - 3BR House Near Disney and Universal Studios

Th10 - 3BR House Near Disney and Universal Studios

3.0 star property

Orlando

The price is €423

€423

includes taxes & fees

28 Oct - 29 Oct

Th10 - 3BR House Near Disney and Universal Studios

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

A porch with a white railing, a blue door, and a potted plant.

A kitchen with white cabinets, a stainless steel stove, and a window with a view of greenery.

8. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!

3.0 star property

Winter Garden

The price is €446

€446

includes taxes & fees

25 Oct - 26 Oct

Fire Pit & Yard: Updated Winter Garden Home!

A residential area with houses featuring sloped roofs and solar panels.

A spacious living area with a white staircase, a dining area, and a kitchen.

A dining area with a table set for four, surrounded by wicker chairs and white upholstered chairs. A staircase with white railings is visible to the left.

A dining area with a black table, white chairs, and a wicker chair. There is a painting on the wall and a white cabinet.

9. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio

3.0 star property

Chatham Park

The price is €221

€221

includes taxes & fees

25 Oct - 26 Oct

Upstay: Bright Family-friendly Retreat With Patio

A single-story building with the number 297, a red door, and a bench outside.

A living room with a television, a coffee table, a sofa, and a rug.

Relax in a cozy, candle-lit living space with plush seating and warm a lighting.

A swimming pool with a unique light display creating patterns on the water's surface.

10. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Lake Mary

9.8 out of 10, Exceptional, (68 reviews)

9.8/10

Exceptional

(68 reviews)

"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"

Gary

The price is €247

€247

includes taxes & fees

3 Nov - 4 Nov

Orlando Pool Days & Hammock Naps Book Your Escape NOW!

A residential property with a red carpet leading to a door, a small garden area with green turf and potted plants, and a wooden fence.

A bathroom with a white sink, a toilet, a mirror, and a glass shower enclosure.

A hotel room with a bed, a chair, a nightstand, a lamp, and a framed sign on the wall.

11. Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

St. Cloud

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Great cute and clean place."

Victoria T.

Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a kitchen island with stools.

An aerial view of a water park with multiple pools, slides, and a large parking area.

A living room with a leather sofa, a wooden coffee table, a TV, and a ceiling fan.

12. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location

3.0 star property

Crestwynd Bay

The price is €355

€355

includes taxes & fees

25 Oct - 26 Oct

Serenity - Family & Pet Friendly, Amazing Location

An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

A modern kitchen with grey cabinets, a white countertop, and stainless steel appliances.

An outdoor bar area with high ceilings, large windows, and a TV screen displaying a nature scene.

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

13. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

3.0 star property

Kissimmee

The price is €738

€738

includes taxes & fees

2 Nov - 3 Nov

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

A spacious living room with a stone fireplace, a ceiling fan, and a large window.

A dining area with two round tables, a kitchen area, and a view of the outdoors.

A long, narrow room with a wooden floor, a table with a tablecloth, and a hammock.

14. Cozy Lake Front Cottage

Cozy Lake Front Cottage

Clermont

10.0 out of 10, Exceptional, (26 reviews)

10/10

Exceptional

(26 reviews)

"Very nice cottage, beautiful view"

rachel c.

The price is €285

€285

includes taxes & fees

25 Oct - 26 Oct

Cozy Lake Front Cottage

A patio with outdoor furniture, a wooden deck, and a basketball hoop.

A bedroom with a bed, a television, a desk, and a fireplace.

A landscaped backyard with a wooden fence, gravel ground, and outdoor lighting.

A modern kitchen with white cabinetry, a built-in microwave, a coffee maker, and a neon 'Peaceful' sign on the wall.

15. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Lake Mary

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"

Chiann M.

The price is €225

€225

includes taxes & fees

2 Nov - 3 Nov

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

A modern living room with a sofa, a large wall clock, and a mirror.

A hallway with a white door, a clock, a sofa, and a potted plant.

A bedroom with two beds, a bedside table with a lamp, a small potted plant, and a desk with drawers.

A bathroom with a bathtub, shower, and toilet. There are toiletries on the counter and a sign with words 'relax', 'soak', and 'unwind'.

16. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Kissimmee

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"

Joyce R.

The price is €188

€188

includes taxes & fees

2 Nov - 3 Nov

Family-Friendly Cottage Near Orlando’s Top Attractions

A resort with multiple buildings, a central pool area, and a lake.

A gym with various exercise machines, treadmills, and weights.

A resort with multiple swimming pools, palm trees, and a parking area.

17. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks

3.0 star property

Orlando

The price is €421

€421

includes taxes & fees

28 Oct - 29 Oct

Th20 - 3BR House With Resort Access Near Parks

A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

A bedroom with a bed, a ceiling fan, and three heart-shaped wall decorations.

A modern kitchen with wooden cabinets, a black refrigerator, a stove, and a microwave.

A dining area with a wooden table, four matching stools, a decorative sign above the table, and a wall-mounted light switch.

18. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation

Kissimmee

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is €177

€177

includes taxes & fees

1 Nov - 2 Nov

Perfect Place for a Perfect Vacation

A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

A modern bathroom with white tiles, a shower with a black rain showerhead, and a toilet.

A swimming pool with a gazebo and a fenced deck area.

A spacious kitchen with a dining area, a sofa, and a ceiling fan.

19. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Kissimmee

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"

Jennifer b.

The price is €285

€285

includes taxes & fees

27 Oct - 28 Oct

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

A cozy outdoor seating area with two wicker chairs, a small wooden table, and a TV mounted on the wall.

A bright living room with a beige sofa, a coffee table, and a colorful rug. There is a window with a view of greenery outside.

A bright living room with a beige sofa, a white coffee table, and a colorful rug featuring cartoon characters.

20. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

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 Orlando Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Rooms were clean, beds and pillows are super soft but supportive. This was the third time visiting and will keep coming back. It is also walking distance to Universal."

Julie 3-night trip

Posted less than an hour ago

DoubleTree by Hilton at the Entrance to Universal Orlando

Coco Key Hotel & Water Park Resort

10/10 Excellent

"I love it"

Natasha 4-night trip

Posted 2 hours ago

Coco Key Hotel & Water Park Resort

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Excelent hotel. The staff was very approachable and always available. Rooms very clean. Suttle always available."

Armando 6-night trip

Posted 3 hours ago

Universal's Endless Summer Resort - Dockside Inn and Suites

Four Points by Sheraton Orlando International Drive

10/10 Excellent

"Very nice"

Javier 1-night trip

Posted 4 hours ago

Four Points by Sheraton Orlando International Drive

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

8/10 Good

"Breakfast is good if you get the right attendant. Hot tub didn’t work and some of the card readers didn’t work. Easy to walk to everywhere if needed."

Sarah 3-night trip

Posted 6 hours ago

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

Universal's Cabana Bay Beach Resort

10/10 Excellent

"We enjoyed every moment. Coming back next year."

Carolina 5-night trip

Posted 16 hours ago

Universal's Cabana Bay Beach Resort

The Point Hotel & Suites Orlando

10/10 Excellent

"Unhook"

Yennifer Alejandra 4-night trip

Posted 18 hours ago

The Point Hotel & Suites Orlando

Rosen Inn, closest to Universal

10/10 Excellent

"Hi we had a lovely stay, could use a little tlc in the rooms, a little spruce up would be a real advantage, i did put these comments in the hotel lobby feedback box ."

susan 14-night trip

Posted 1 day ago

Rosen Inn, closest to Universal

Find out more about Southwest Orlando