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7 BEDS | 5.5 BATHS GamesRoom & Pool/spa 3907lana in Davenport From US $423
         

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Boat Rental
7 BEDS | 5.5 BATHS GamesRoom & Pool/spa 3907lana
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Luxury Places to Stay in Hillcrest Estates

Over 10000+ Luxury Places to Stay in or Near Hillcrest Estates
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House
Superb Resort Townhouse Close To Disney
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House
4 Bedroom Paradise Palms With Private Pool (2600)
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8.8 (3 Reviews)
House
BRAND NEW Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER Themed Rooms
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House
Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER - DISNEY AREA
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House
FROZEN & HARRY POTTER Themed Rooms * Solara Resort - 5 bedrooms, Private Pool
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Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #31376 in Orlando From US $8,725
         

New
Villa
Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #31376
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Stunning Themed 5Bed Townhome Splash Pool-2307DST in Kissimmee From US $6,258
         

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House
Stunning Themed 5Bed Townhome Splash Pool-2307DST
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9BR Family Mansion with Pool & Hot Tub in Kissimmee From US $5,900
         

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9BR Family Mansion with Pool & Hot Tub
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Top-Rated Vacation Rentals with a Pool in Hillcrest Estates

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Hillcrest Estates
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192 in Kissimmee From US $218
         

10.0 (334 Reviews)
Villa
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
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Water View - Pool & Spa - 3.5 miles to Disney - BBQ in Kissimmee From US $313
         

10.0 (325 Reviews)
House
Water View - Pool & Spa - 3.5 miles to Disney - BBQ
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Amazing villa close to Disney with 5* Reviews in kissimmee From US $365
         

10.0 (283 Reviews)
Villa
Amazing villa close to Disney with 5* Reviews
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OWNER PAID RESORT FEES🌟 All Inclusive 3BR/3BA "PRIME LOCATION NEAR DISNEY"💥 in Davenport From US $269
         

10.0 (274 Reviews)
House
OWNER PAID RESORT FEES🌟 All Inclusive 3BR/3BA "PRIME LOCATION NEAR DISNEY"💥
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💥$40 OFF SALE TOP RATED ALL-INCLUSIVE HOME. NEAR DISNEY PRIME LOCATION 💥 in Davenport From US $209
         

10.0 (272 Reviews)
House
💥$40 OFF SALE TOP RATED ALL-INCLUSIVE HOME. NEAR DISNEY PRIME LOCATION 💥
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5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill. in Kissimmee From US $390
         

10.0 (227 Reviews)
House
5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
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Elegant, Spacious Townhome within 4 Miles to Walt Disney World in Kissimmee From US $239
         

10.0 (198 Reviews)
House
Elegant, Spacious Townhome within 4 Miles to Walt Disney World
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Platinum Updated Modern 2BR at Bahama Bay – 15 Min to Disney in Davenport From US $185
         

10.0 (192 Reviews)
Condo
Platinum Updated Modern 2BR at Bahama Bay – 15 Min to Disney
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Pet-Friendly Vacation Rentals in Hillcrest Estates

Over 3430+ Pet-Friendly Vacation Rentals in or Near Hillcrest Estates
Sunset View, lake view, game room, Windsor at Westside resort, Nr Disney/Golf in Kissimmee From US $456
         

9.8 (132 Reviews)
Villa
Sunset View, lake view, game room, Windsor at Westside resort, Nr Disney/Golf
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22 Bedroom Disney Area Golf Resort Estate Mansion in Davenport From US $1,459
         

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1.0 (1 Review)
House
22 Bedroom Disney Area Golf Resort Estate Mansion
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Bahama Sunset 5 Bedrooms in Davenport From US $653
         

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10.0 (3 Reviews)
House
Bahama Sunset 5 Bedrooms
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Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2 in Kissimmee From US $140
         

9.6 (212 Reviews)
Condo
Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
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Family-Friendly Vacation Villa Near Disney – Space, Comfort & Fun for Everyone in Clermont From US $245
         

9.4 (142 Reviews)
Villa
Family-Friendly Vacation Villa Near Disney – Space, Comfort & Fun for Everyone
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9Br/6Ba lake view Pool House from 300/nt, Close To Disney in Kissimmee From US $466
         

9.2 (71 Reviews)
House
9Br/6Ba lake view Pool House from 300/nt, Close To Disney
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9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney in Kissimmee From US $385
         

8.4 (19 Reviews)
House
9Br/6Ba luxurious Pool House with lake view from 280/nt, Close To Disney
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DisneyEstate by AmericanVacationLiving 11BR in Davenport From US $948
         

10.0 (8 Reviews)
Villa
DisneyEstate by AmericanVacationLiving 11BR
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Large Vacation Homes & Villas in Hillcrest Estates

Over 15155+ Large Vacation Homes & Villas in or Near Hillcrest Estates
Private Pool/Spa, Outdoor TV, Woodland Views, Windsor Palms, Minutes to Disney in Kissimmee From US $427
         

10.0 (125 Reviews)
Villa
Private Pool/Spa, Outdoor TV, Woodland Views, Windsor Palms, Minutes to Disney
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Discover Unparalleled Elegance Our Newest Candlelight Pool Home in Kissimmee From US $285
         

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Discover Unparalleled Elegance Our Newest Candlelight Pool Home
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PROMO Breathtaking 8 BR Villa, Pool, Resort - by Blue Sky Villas in Kissimmee From US $1,574
         

9.8 (8 Reviews)
House
PROMO Breathtaking 8 BR Villa, Pool, Resort - by Blue Sky Villas
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Hampton Lakes Luxury 4 Bed Villa, Games room, FREE Internet access, Lake View in Davenport From US $231
         

10.0 (123 Reviews)
Villa
Hampton Lakes Luxury 4 Bed Villa, Games room, FREE Internet access, Lake View
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Luxury Villa, Near Disney, Davenport, Orlando, Florida. USA. in Davenport From US $271
         

10.0 (59 Reviews)
Villa
Luxury Villa, Near Disney, Davenport, Orlando, Florida. USA.
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Ideal family villa/large private pool/not overlooked/near Disney/on golf course in Davenport From US $495
         

9.8 (120 Reviews)
Villa
Ideal family villa/large private pool/not overlooked/near Disney/on golf course
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✦ 5min2Disney ✦ 7BR/4.5BA ✦ South Pool/Spa ✦ A/C Star Wars Gameroom ✦ Modern in Kissimmee From US $367
         

9.8 (47 Reviews)
Villa
✦ 5min2Disney ✦ 7BR/4.5BA ✦ South Pool/Spa ✦ A/C Star Wars Gameroom ✦ Modern
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3 MILES FROM DISNEY! Private SOUTH facing Pool. Awesome family villa in Kissimmee From US $220
         

9.6 (242 Reviews)
Villa
3 MILES FROM DISNEY! Private SOUTH facing Pool. Awesome family villa
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Wheelchair Accessible Vacation Homes in Hillcrest Estates

Over 1161+ Wheelchair Accessible Vacation Homes in or Near Hillcrest Estates
Amazing house with a nice private pool near Disney in Orlando From US $100
         

8.0 (12 Reviews)
Villa
Amazing house with a nice private pool near Disney
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Ultimate Orlando Adventure: Orange Lake Resort - Disney, Universal, Sea World! in Kissimmee From US $219
         

9.6 (8 Reviews)
Villa
Ultimate Orlando Adventure: Orange Lake Resort - Disney, Universal, Sea World!
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2 Mi to Animal Kingdom: Kissimmee Resort Condo! in Kissimmee From US $295
         

9.8 (14 Reviews)
Condo
2 Mi to Animal Kingdom: Kissimmee Resort Condo!
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Winter Discount! Amenity filled resort, Near Disney, No Resort Fees in davenport From US $147
         

9.2 (106 Reviews)
Condo
Winter Discount! Amenity filled resort, Near Disney, No Resort Fees
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Beautiful 4bed condo w full size baby crib, resort amenities, near Disney in Davenport From US $211
         

7.4 (12 Reviews)
Condo
Beautiful 4bed condo w full size baby crib, resort amenities, near Disney
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Lovely Condo 10 Minutes from Disney! in Davenport From US $223
         

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Condo
Lovely Condo 10 Minutes from Disney!
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Quiet condo close to Disney World, fully furnished, No Resort Fee in Davenport From US $183
         

9.8 (24 Reviews)
Condo
Quiet condo close to Disney World, fully furnished, No Resort Fee
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Quiet Moana Retreat in gated community– Perfect for Disney & Universal Visitors in Kissimmee From US $380
         

10.0 (33 Reviews)
Condo
Quiet Moana Retreat in gated community– Perfect for Disney & Universal Visitors
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Hillcrest Estates Vacation Rentals and Airbnb Places to Stay Under $200

Over 5114+ Hillcrest Estates Vacation Rentals and Airbnb Places to Stay Under $200
The Pixie Nest in Kissimmee From US $118
         

9.0 (3 Reviews)
Apartment
The Pixie Nest
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4BR Private Pool Home Near Disney – Family Friendly Sleeps 8 Screened Pool in Kissimmee From US $190
         

10.0 (50 Reviews)
House
4BR Private Pool Home Near Disney – Family Friendly Sleeps 8 Screened Pool
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Beautiful family home close to all attractions. in Kissimmee From US $127
         

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House
Beautiful family home close to all attractions.
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Platinum rated 2BR ground floor next to pool big screen TVs, Huge patio, wifi in Davenport From US $156
         

9.8 (60 Reviews)
Condo
Platinum rated 2BR ground floor next to pool big screen TVs, Huge patio, wifi
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1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney! in Kissimmee From US $185
         

10.0 (48 Reviews)
Condo
1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney!
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3 Bedroom Bahama Bay Resort Condo - Peaceful Location - Near Disney & Universal in Davenport From US $175
         

9.6 (104 Reviews)
Apartment
3 Bedroom Bahama Bay Resort Condo - Peaceful Location - Near Disney & Universal
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GUESTS LOVE THIS LUXURY 4 BED VILLA, PRIVATE POOL, GAMES ROOM & NOT OVERLOOKED in Davenport From US $171
         

9.4 (144 Reviews)
Villa
GUESTS LOVE THIS LUXURY 4 BED VILLA, PRIVATE POOL, GAMES ROOM & NOT OVERLOOKED
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Poolside 2 Bedroom/2 Bathroom Condo Close to Disney! in Kissimmee From US $167
         

9.8 (82 Reviews)
Condo
Poolside 2 Bedroom/2 Bathroom Condo Close to Disney!
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Instantly Bookable Vacation Homes in Hillcrest Estates

Over 15581+ Instantly Bookable Vacation Homes in or Near Hillcrest Estates
Stunning Lakeview Pool/Spa-Games Room,Free Wi-Fi, 2 mls to Disney in Kissimmee From US $351
         

9.8 (104 Reviews)
House
Stunning Lakeview Pool/Spa-Games Room,Free Wi-Fi, 2 mls to Disney
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Luxury Theme Park & Golf Retreat in Davenport From US $347
         

9.2 (9 Reviews)
House
Luxury Theme Park & Golf Retreat
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4 Bedrooms 3.5 Bathrooms - Inc 2 King Bed Master Suites-Next to Disney World in Kissimmee From US $240
         

9.8 (104 Reviews)
House
4 Bedrooms 3.5 Bathrooms - Inc 2 King Bed Master Suites-Next to Disney World
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DISNEY VILLA LOCATION! 5BR/private POOL/game room/10 MILES TO DISNEY in Davenport From US $270
         

9.4 (177 Reviews)
House
DISNEY VILLA LOCATION! 5BR/private POOL/game room/10 MILES TO DISNEY
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Step into the villa and you will go WOW!-3 miles to Disney in Kissimmee From US $251
         

9.4 (134 Reviews)
Villa
Step into the villa and you will go WOW!-3 miles to Disney
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4 Bedroom Townhouse-Regal Palms Resort-Close to Pool and Disney,Wi-Fi in Davenport From US $203
         

9.6 (142 Reviews)
House
4 Bedroom Townhouse-Regal Palms Resort-Close to Pool and Disney,Wi-Fi
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Beautiful 4BR/3 ba House-3miles Disney large pool/spa/XLdeck-Wheelchair friendly in Kissimmee From US $249
         

9.6 (207 Reviews)
House
Beautiful 4BR/3 ba House-3miles Disney large pool/spa/XLdeck-Wheelchair friendly
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Emerald Island Luxury Castle in Kissimmee, Private Pool, 3 mi to Disney Parks in Kissimmee From US $599
         

9.6 (85 Reviews)
House
Emerald Island Luxury Castle in Kissimmee, Private Pool, 3 mi to Disney Parks
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About Hillcrest Estates Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sailings Hillcrest Estates, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Hillcrest Estates. Places to stay near Hillcrest Estates with prices averaging US $423 a night.

Sailings makes it easy and safe to find and compare vacation rentals in Hillcrest Estates with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Hillcrest Estates

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Use these Quick Filters to Find a Vacation Rental in Hillcrest Estates

★ Pro Tip: Sailings makes it easy to compare the best listings on Sailings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sailings homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Hillcrest Estates.

Weather in Hillcrest Estates

View the weather forecast for Hillcrest Estates before booking your Hillcrest Estates Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Hillcrest Estates, FL


Disney 4 Properties Hillcrest Estate 2 Properties Theme Park Adventure Comfy Attractions Restaurant 1 Properties

Hillcrest Estates Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Hillcrest Estates?

There are a lot of options in Hillcrest Estates. If you plan on staying in the Hillcrest Estates area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillcrest Estates:

Which vacation homes in Hillcrest Estates are best for families?

If you are looking for a family-friendly vacation home in Hillcrest Estates, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillcrest Estates:

How many vacation rentals are available in Hillcrest Estates?

Currently, the total number of properties listed in 2026 is over 1 in the Hillcrest Estates area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Hillcrest Estates.