
Holiday rentals near Pioneer Village at Shingle Creek
We found 17,562 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Pioneer Village at Shingle Creek that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Pioneer Village at Shingle Creek
Showing deals for:21 Nov - 28 Nov
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
8% off
Price is £11,716
£11,716
£1,674 nightly
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
7% off
Price is £1,262
£1,262
£180 nightly
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
7% off
Price is £1,077
£1,077
£154 nightly
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
7% off
Price is £2,629
£2,629
£376 nightly
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
7% off
Price is £1,416
£1,416
£202 nightly
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
7% off
Price is £1,871
£1,871
£267 nightly
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
7% off
Price is £4,100
£4,100
£586 nightly
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
7% off
Price is £1,819
£1,819
£260 nightly
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
7% off
Price is £4,088
£4,088
£584 nightly
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
7% off
Price is £4,166
£4,166
£595 nightly
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
7% off
Price is £3,484
£3,484
£498 nightly
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
13% off
Price is £1,234
£1,234
£176 nightly
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
7% off
Price is £1,184
£1,184
£169 nightly
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
6% off
Price is £1,265
£1,265
£181 nightly
Includes taxes & fees
Image gallery for NEW VILLA 6-Bedrooms with private pool and Free Water Park

9.69.6 out of 10 rating
Exceptional
(24 reviews)
NEW VILLA 6-Bedrooms with private pool and Free Water Park
Kissimmee, FL
7% off
Price is £2,101
£2,101
£300 nightly
Includes taxes & fees
Image gallery for Charming 4br home in residential neighborhood!

8.68.6 out of 10 rating
Excellent
(23 reviews)
Charming 4br home in residential neighborhood!
Davenport, FL
7% off
Price is £917
£917
£131 nightly
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
7% off
Price is £5,972
£5,972
£853 nightly
Includes taxes & fees
Image gallery for Beautiful home near Disney Private PoolBBQ Downtown

9.89.8 out of 10 rating
Exceptional
(29 reviews)
Beautiful home near Disney Private PoolBBQ Downtown
Kissimmee, FL
7% off
Price is £1,397
£1,397
£200 nightly
Includes taxes & fees
Image gallery for Sleeps 10 + Pool and Fully Fenced Yard plus enjoys 2 King Rooms

1010 out of 10 rating
Exceptional
(15 reviews)
Sleeps 10 + Pool and Fully Fenced Yard plus enjoys 2 King Rooms
Orlando, FL
7% off
Price is £1,712
£1,712
£245 nightly
Includes taxes & fees
Image gallery for Arcades, Foosball, Jumbo Chess, Indoor Tiki Bar, 10 mins to Disney: Flamingo Bay

9.49.4 out of 10 rating
Exceptional
(49 reviews)
Arcades, Foosball, Jumbo Chess, Indoor Tiki Bar, 10 mins to Disney: Flamingo Bay
Kissimmee, FL
7% off
Price is £5,143
£5,143
£735 nightly
Includes taxes & fees
Image gallery for Pet Friendly w/ Large Private Pool | Corner Unit | Sleeps 9

8.48.4 out of 10 rating
Very good
(60 reviews)
Pet Friendly w/ Large Private Pool | Corner Unit | Sleeps 9
Kissimmee, FL
15% off
Price is £1,107
£1,107
£158 nightly
Includes taxes & fees
Image gallery for (WE2738) Storey Lake Home 5/5, Private Pool & Free Waterpark

9.29.2 out of 10 rating
Wonderful
(45 reviews)
(WE2738) Storey Lake Home 5/5, Private Pool & Free Waterpark
Kissimmee, FL
7% off
Price is £1,904
£1,904
£272 nightly
Includes taxes & fees
Image gallery for -BIG DISNEY FAMILY HOME-Priv Pool, Arcade, Lake Views, 4b/4ba. Close to Parks

1010 out of 10 rating
Exceptional
(19 reviews)
-BIG DISNEY FAMILY HOME-Priv Pool, Arcade, Lake Views, 4b/4ba. Close to Parks
Kissimmee, FL
7% off
Price is £1,569
£1,569
£224 nightly
Includes taxes & fees
Image gallery for FA4381 Storey Lake Home 4Beds 3baths Private Pool and Free Waterpark

8.88.8 out of 10 rating
Excellent
(42 reviews)
FA4381 Storey Lake Home 4Beds 3baths Private Pool and Free Waterpark
Kissimmee, FL
7% off
Price is £1,264
£1,264
£181 nightly
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
Highly recommend
1010 out of 10
Exceptionalexceptional
230 reviews(230 reviews)
Highly recommend this property. Spacious, super clean and comfortable. Nice touch to supply dishwasher tablets and laundry pods. We will be back.
John E.
Stayed May 2025
Holiday 2025
1010 out of 10
Exceptionalexceptional
250 reviews(250 reviews)
Great time had by all. A quiet villa tucked away. Saw and heard some local wildlife. Good response when needed from owner. Michaela
Michaela S.
Stayed May 2025
Exceptional property for multi generational holiday
1010 out of 10
Exceptionalexceptional
219 reviews(219 reviews)
Our family holiday at the villa was exceptional. Clean and spacious rooms, more TVs than our local TV shop, games room and supurb pool area (projector screen added during our stay).
We were using the Villa as our base for visits to local attractions and the host left plenty of information and local tips that greatly helped when getting our bearings. The pool was obviously our focal point of activity, with 3 children and several child like adults. Many blow up animals were purchased and the jacuzzi proved popular with non-swimmers.
The bedrooms and attached en-suites were spacious, comfortable but most of all cool to sleep in, with ceiling fans and great air conditioning.
If you are looking for a base for a large family group within throwing distance from all of the Florida attractions, this should be it.
Bryan S.
Stayed Oct 2024
The Martens
1010 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
Cleanliness was good, everything we needed was provided, very spacious, swimming pool was great. Very close to all the Disney parks and supermarkets, restaurants. Would highly recommend.
Joanne M.
Stayed Aug 2024
Family wedding holiday
1010 out of 10
Exceptionalexceptional
218 reviews(218 reviews)
Great location our host John, kept us informed throughput, felt nice and safe, great size very well equipped villa.
So easy to get to 10 minutes to Disney and only 35 minutes to Universal in daytime traffic.
Loved the large pool and great size bedrooms.
Will be booking again.
Stuart H.
Stayed May 2024
Brilliant location , wonderful attention to detail
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
We’ve stayed at numerous properties in Windsor Hills over the past 8 years but this one is now our favourite . The theming of the rooms is excellent as can be seen in the photos but another selling point for us was the view from the pool . We had some amazing sunsets and wildlife to watch on those nights when we were home from the parks early . Previously we’ve stayed in great houses but the pools have been looking onto brick walls or other properties . We couldn’t go back to that now . Hoping to be back soon , thanks for having us .
Alan B.
Stayed Oct 2023
Beautiful
1010 out of 10
Exceptionalexceptional
236 reviews(236 reviews)
A beautiful house. Barbara was extremely helpful throughout the stay. Especially when we were tired after traveling and forgot how to log in at venue. The house was in an extremely pleasant area, gate guarded. Also very close to all parks, 20 - 30 mins from parks.
Mark G.
Stayed Aug 2023
Wonderful stay!
1010 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
The house is exactly as listed, very spacious, clean and comfortable. Great communication with the owner, very grateful for her help and all the extras already in the home- most of necessities catered for so saved us having to buy. Windsor Hills is a well managed and safe feeling community and everyone was very friendly. Only recommendations would be (not a criticism at all) would be for Windsor Hills to have a bar area at main pool as we thought there was one- you buy premixed cocktails from the shop. Also would recommend a shelf in showers of the house for shampoos and stuff and hooks in bathroom areas to hang towels after use.
We all really enjoyed the house and pool and all agreed we would definitely stay again!
Colleen P.
Stayed Aug 2023
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
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- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value