
Vacation rentals near Pioneer Village at Shingle Creek
We found 17,562 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals within easy reach of Pioneer Village at Shingle Creek that can be your home away from home. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the amenities you expect for your stay, which might include parking and a washer and dryer. No matter what you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Pioneer Village at Shingle Creek
Showing deals for:Nov 21 - Nov 28
Image gallery for Upstay - Patio Paradise w Pool Spa Games & TikiBar

8.88.8 out of 10 rating
Excellent
(8 reviews)
Upstay - Patio Paradise w Pool Spa Games & TikiBar
Kissimmee, FL
10% off
Price is CA $2,361
CA $2,361
CA $20,740 total
CA $20,740 total
includes taxes & fees
Image gallery for Spacious Vacation Home 20 min from Theme Parks!

9.29.2 out of 10 rating
Wonderful
(56 reviews)
Spacious Vacation Home 20 min from Theme Parks!
Kissimmee, FL
10% off
Price is CA $237
CA $237
CA $2,298 total
CA $2,298 total
includes taxes & fees
Image gallery for NEW Home 3 Bedrooms Water View DISNEY UNIVERSAL

1010 out of 10 rating
Exceptional
(15 reviews)
NEW Home 3 Bedrooms Water View DISNEY UNIVERSAL
Kissimmee, FL
10% off
Price is CA $199
CA $199
CA $1,971 total
CA $1,971 total
includes taxes & fees
Image gallery for Spacious Family Retreat w Pool, BBQ & Ping Pong

8.68.6 out of 10 rating
Excellent
(7 reviews)
Spacious Family Retreat w Pool, BBQ & Ping Pong
Kissimmee, FL
10% off
Price is CA $501
CA $501
CA $4,770 total
CA $4,770 total
includes taxes & fees
Image gallery for Private Pool & Spa Only 8 mi to Disney! Gated Community Book 7+ Nights & Save!

1010 out of 10 rating
Exceptional
(66 reviews)
Private Pool & Spa Only 8 mi to Disney! Gated Community Book 7+ Nights & Save!
Kissimmee, FL
10% off
Price is CA $263
CA $263
CA $2,568 total
CA $2,568 total
includes taxes & fees
Image gallery for Family Retreat w/ Pool, Lake View & Disney Nearby – 5BR Storey Lake Getaway

1010 out of 10 rating
Exceptional
(13 reviews)
Family Retreat w/ Pool, Lake View & Disney Nearby – 5BR Storey Lake Getaway
Kissimmee, FL
10% off
Price is CA $347
CA $347
CA $3,347 total
CA $3,347 total
includes taxes & fees
Image gallery for Ultimate Lakeview Villa with Everything!

9.89.8 out of 10 rating
Exceptional
(372 reviews)
Ultimate Lakeview Villa with Everything!
Kissimmee, FL
10% off
Price is CA $754
CA $754
CA $7,301 total
CA $7,301 total
includes taxes & fees
Image gallery for Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!

9.29.2 out of 10 rating
Wonderful
(20 reviews)
Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!
Kissimmee, FL
5% off
Price is CA $173
CA $173
CA $1,748 total
CA $1,748 total
includes taxes & fees
Image gallery for 6 Bedroom Themed Villa Near Disney World with Pool, Hot tub & Private Game Room

1010 out of 10 rating
Exceptional
(67 reviews)
6 Bedroom Themed Villa Near Disney World with Pool, Hot tub & Private Game Room
Kissimmee, FL
5% off
Price is CA $322
CA $322
CA $3,261 total
CA $3,261 total
includes taxes & fees
Image gallery for Magical 5 BD/4 BATH with Poolside Cinema and Free Resort! Sleeps 14

1010 out of 10 rating
Exceptional
(37 reviews)
Magical 5 BD/4 BATH with Poolside Cinema and Free Resort! Sleeps 14
Kissimmee, FL
10% off
Price is CA $337
CA $337
CA $3,287 total
CA $3,287 total
includes taxes & fees
Image gallery for Lakeview Condo minutes to Convention Center, Disney & Universal Studio

9.09.0 out of 10 rating
Wonderful
(31 reviews)
Lakeview Condo minutes to Convention Center, Disney & Universal Studio
Orlando, FL
5% off
Price is CA $238
CA $238
CA $2,045 total
CA $2,045 total
includes taxes & fees
Image gallery for Kissimmee Retreat w/ Pool: Near Disney & Golf!

9.09.0 out of 10 rating
Wonderful
(117 reviews)
Kissimmee Retreat w/ Pool: Near Disney & Golf!
Kissimmee, FL
5% off
Price is CA $206
CA $206
CA $2,248 total
CA $2,248 total
includes taxes & fees
Image gallery for Spacious Family Home, private Pool/Spa, Game Rm near Disney and Champions Gate

8.88.8 out of 10 rating
Excellent
(75 reviews)
Spacious Family Home, private Pool/Spa, Game Rm near Disney and Champions Gate
Orlando, FL
5% off
Price is CA $288
CA $288
CA $2,940 total
CA $2,940 total
includes taxes & fees
Image gallery for Lakeview Storey Lake 10BR/5BA-Pool/Spa/Rec-Close to Disney/Universal Studios

9.89.8 out of 10 rating
Exceptional
(46 reviews)
Lakeview Storey Lake 10BR/5BA-Pool/Spa/Rec-Close to Disney/Universal Studios
Kissimmee, FL
10% off
Price is CA $766
CA $766
CA $7,354 total
CA $7,354 total
includes taxes & fees
Image gallery for Stunning Spacious 4br Kissimmee/orlando Villa W/private Pool And Whirlpool Spa

9.69.6 out of 10 rating
Exceptional
(85 reviews)
Stunning Spacious 4br Kissimmee/orlando Villa W/private Pool And Whirlpool Spa
Kissimmee, FL
5% off
Price is CA $220
CA $220
CA $2,111 total
CA $2,111 total
includes taxes & fees
Image gallery for Spacious Pool Home, 6 miles to Disney, Gated Resort, Amenities for All

9.29.2 out of 10 rating
Wonderful
(49 reviews)
Spacious Pool Home, 6 miles to Disney, Gated Resort, Amenities for All
Orlando, FL
5% off
Price is CA $180
CA $180
CA $1,937 total
CA $1,937 total
includes taxes & fees
Image gallery for Family Friendly Home, South-facing Pool/Spa, Game Rm, Gated Resort near Disney

9.09.0 out of 10 rating
Wonderful
(59 reviews)
Family Friendly Home, South-facing Pool/Spa, Game Rm, Gated Resort near Disney
Orlando, FL
5% off
Price is CA $259
CA $259
CA $2,703 total
CA $2,703 total
includes taxes & fees
Image gallery for Lakeview Luxury Villa with Everything

9.89.8 out of 10 rating
Exceptional
(103 reviews)
Lakeview Luxury Villa with Everything
Kissimmee, FL
10% off
Price is CA $776
CA $776
CA $7,493 total
CA $7,493 total
includes taxes & fees
Image gallery for *8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!

9.89.8 out of 10 rating
Exceptional
(62 reviews)
*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!
Kissimmee, FL
10% off
Price is CA $667
CA $667
CA $6,233 total
CA $6,233 total
includes taxes & fees
Image gallery for BEST HOUSE! Harry Potter, StarWars, Moana, Princess, Avengers. Disney 8-10 min!

1010 out of 10 rating
Exceptional
(157 reviews)
BEST HOUSE! Harry Potter, StarWars, Moana, Princess, Avengers. Disney 8-10 min!
Kissimmee, FL
5% off
Price is CA $1,115
CA $1,115
CA $10,134 total
CA $10,134 total
includes taxes & fees
Image gallery for Modern Compass Bay Corner Unit w/ Game Room | Pet Friendly | Sleeps 10

9.29.2 out of 10 rating
Wonderful
(71 reviews)
Modern Compass Bay Corner Unit w/ Game Room | Pet Friendly | Sleeps 10
Kissimmee, FL
20% off
Price is CA $198
CA $198
CA $2,209 total
CA $2,209 total
includes taxes & fees
Image gallery for JB201 Storey Lake Condo 3 Bed 2 Bath Free Waterpark

9.69.6 out of 10 rating
Exceptional
(15 reviews)
JB201 Storey Lake Condo 3 Bed 2 Bath Free Waterpark
Kissimmee, FL
10% off
Price is CA $215
CA $215
CA $2,136 total
CA $2,136 total
includes taxes & fees
Image gallery for Pool home near Disney parks.

9.49.4 out of 10 rating
Exceptional
(50 reviews)
Pool home near Disney parks.
Kissimmee, FL
8% off
Price is CA $231
CA $231
CA $2,305 total
CA $2,305 total
includes taxes & fees
Image gallery for Mustang Pool Table, Arcades, Huge Treehouse, 007 Bedroom: Hidden Gem

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Mustang Pool Table, Arcades, Huge Treehouse, 007 Bedroom: Hidden Gem
Kissimmee, FL
10% off
Price is CA $1,110
CA $1,110
CA $10,696 total
CA $10,696 total
includes taxes & fees
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Find the best place to stay - Pioneer Village at Shingle Creek
Sunset Estate: New 15 Bedroom Luxury Vacation Rental Near Disney.
Sleeps 30 · 15 bedrooms · 15+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
Seven Dwarfs Resort -Close to Disney
Sleeps 6 · 3 bedrooms
6.86.8 out of 10
5 reviews(5 reviews)
Ultimate Lakeview Villa with Everything!
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.49.4 out of 10
Exceptionalexceptional
134 reviews(134 reviews)
Upstay: Luxury 10BR Mansion w Pool,Hot Tub & Games
Sleeps 20 · 10 bedrooms · 8 bathrooms
8.08.0 out of 10
Very goodvery good
4 reviews(4 reviews)
Disney area 5* Villa with private pool, spa, Wi-Fi & Games in gated Aviana community
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
215 reviews(215 reviews)
Upstay Luxury Resort Home w Private Pool & Hot Tub
Sleeps 20 · 10 bedrooms · 8 bathrooms
9.29.2 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
Top rated rentals - Pioneer Village at Shingle Creek
Little getaway
1010 out of 10
Exceptionalexceptional
250 reviews(250 reviews)
Great overall stay at this house. We will gladly return in the future for another stay. Overall communication was great with Terry and everything was easily explained. Great house and pool area. Very quiet area as well.
Jamie V.
Stayed Jun 2025
Pool View
1010 out of 10
Exceptionalexceptional
294 reviews(294 reviews)
My family and I had the best time staying here at Windsor Hills. The condo is super clean, close to stores, restaurants and Disney parks. It come with everything you need. Communication from booking to chrck out was smooth and easy. 10/10 would stay here again!
Erin S.
Stayed May 2025
Beautiful house!
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
This house had plenty of room for the 8 of us to sprawl out. Our kids loved the themed rooms and LOVED the arcade room. Host was very responsive to any questions I had and was very helpful. Would definitely stay here again.
Erin M.
Stayed Apr 2025
Excellent Home away from Home
1010 out of 10
Exceptionalexceptional
236 reviews(236 reviews)
We stayed for nine nights, and everything about this villa was great. Clean, comfortable, and just as good as the pictures portrayed. Barbara was lovely to work with, provided clear check-in and out instructions, offered and gave some excellent Disney tips, and was very responsive to messages. The grounds staff were lovely, and the pool was awesome, and a real life-saver after hot days at the parks. Location was great - super easy to get to all of the parks. Would absolutely recommend, and will definitely consider if/when we go again.
Brittany C.
Stayed Apr 2025
As advertised and more.
1010 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
Everything was exactly as advertised.Amenities, cleanliness, and communication.We rarely needed to contact them, but when we did the response was fast and helpful. We would strongly recommend this property.
Malcolm G.
Stayed Mar 2025
Excellent Stay
1010 out of 10
Exceptionalexceptional
230 reviews(230 reviews)
We had a great time at this property. Beds were very comfortable. House was very clean. Had all the amenities we needed. Short drive to Disney. Lots of restaurants close by. Alfredo was a great host. Would stay again next time we are in Orlando.
Laszlo P.
Stayed Feb 2025
Family/Friends Vacation
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The host was absolutely amazing to work with through the whole process. Location is amazing and the amenities included with staying here are absolutely fantastic! This house was the perfect home away from home for our family/friends vacation!
Leanne H.
Stayed Feb 2025
Excellent vacation
1010 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
Home was better than expected, equipped with everything we needed. Conveniently located in secure gated community. Home owner responds very quickly to any questions. Would highly recommend this home!
Nancy & Sherwyn M.
Stayed Nov 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value