Luxury rentals in Winter Park

An expansive mountain estate is framed by tall trees and a colorful sunset sky. The exterior showcases a blend of stone and wood, with multiple balconies accessible by a curved staircase. A spacious driveway leads to a two-car garage, flanked by carefully arranged landscaping.

4.86 out of 5 average rating, 22 reviews

Sleeps 19 | Winterhaven Estate by AvantStay

- Private, expansive compound in Winter Park, offering space, comfort, and stunning alpine views. - The Lodge, Bungalow, and Bunkhouse provide both togetherness and privacy for large groups. - Perfect for corporate retreats, celebrations, or multi-generational family gatherings. - Multiple balconies, a hot tub, firepit, and outdoor dining create the ideal atmosphere for relaxation and connection. - Free shuttle access to Winter Park Resort, downtown Winter Park, and the Fraser River Trail.

Indoor spacesHospitalityLocationKitchenDecorComfortFamilyViewCleanlinessSleep qualityAmenitiesBathroomWifiSkiingTVAccuracyWalkabilityHot tubAccess

5.0 out of 5 average rating, 15 reviews

Secluded Ranch Creek Home: Hot tub & Chefs kitchen

Escape to a one-of-a-kind architect-designed mountain retreat on 35 private acres near Fraser, CO. Enjoy complete privacy, panoramic views, and luxury finishes throughout. Gather around the unique pass-through gas fireplace, relax in the screened porch with a wood-burning fireplace, or spread out between two living areas. Families will love the kids' room, while the heated garage, radiant floor heat, gourmet kitchen, private hot tub, and wraparound deck make every season unforgettable.

HospitalityFamilyCleanlinessLocationKitchenIndoor spacesHot tubComfortRiverSkiingAccuracyOutdoor spacesBathroomHikingCheckoutHeatingNearby

4.6 out of 5 average rating, 10 reviews

Riverwalk Luxury Home Steps to River, Town & Trail

Stay in Riverwalk, Winter Park’s only luxury residential community, offering a level of design, privacy, and experience you won’t find anywhere else in the area. Riverwalk is Winter Park's exclusive luxury community. This 5-bed, 7-bath modern mountain retreat comfortably sleeps 16. Features include a chef's kitchen, private 8-person hot tub, and stunning indoor-outdoor living spaces with private river access. Perfect for large families and groups seeking privacy and high-end design.

HospitalityIndoor spacesLocationWalkabilityGetting aroundNoiseNearbyFamilyCleanlinessAccuracyBathroomSleep qualityKitchenDecorConditionTVViewGrillLayoutComfortAmenities

5.0 out of 5 average rating, 10 reviews

A spacious modern home is situated in a snowy landscape, featuring large windows that offer mountain views. The exterior showcases a combination of dark wood and stonework, along with a covered deck that extends from the main structure, inviting outdoor relaxation.

Home in Granby

Breathtaking Mountain Manor, Huge Deck w/ Hot Tub,

Discover pure perfection in this brand-new home located in Granby Ranch, where exquisite craftsmanship and uncompromising quality shine through every aspect of its design and construction. This magnificent home boasts 6 bedrooms, 5.5 bathrooms, and TWO flex spaces, making it feel more like an 8 bedroom home. 4,659 square feet of lavish comfort with jaw-dropping stonework inside and outside.

LocationHospitalityKitchenFamilyComfortGetting aroundSkiingViewBathroomCleanlinessAmenities

Roam River Home - Endless Amenities - Must View

Downtown Winter Park Roam River Home / Huge Inground 12 Person Hot Tub / Amazing Views / Multiple Gas Firepits / Roof Top Deck With Bar / Outdoor Sauna / Steam Room / Office / Nordic Track Bike / Car Charger / Arcade Games / Home Theatre / Incredible Bunk Room for 8 with Secret Playrooms / Walk to Shopping-Restaurants-Entertainment / Discounted Attractions

AmenitiesFamily

A rooftop patio features a private hot tub surrounded by comfortable outdoor seating, illuminated by string lights. The backdrop showcases a vibrant sunset, casting warm colors across the sky and offering panoramic views of the surrounding landscape.

4.91 out of 5 average rating, 46 reviews

Downtown WP River Villa 104 - Rooftop Hot Tub

Downtown Winter Park River Front Villa / Rooftop Lounge With Hot Tub - Gas Firepit - Bar - Dining - Sectional / Amazing Views / Bunk Room / Multi Game Table / Car Charger / Desk Area / Walk to Shopping-Restaurants-Entertainment / Discounted Attractions

LocationFamilyHospitalityIndoor spacesKitchenCleanlinessViewWalkabilityHot tubSkiingComfortNearbyDecorBathroomGetting aroundConditionAccuracySleep qualityHeatingValueOutdoor spacesLayoutAmenitiesTVRiverAccessCheckoutCheck-inPetsGrillParksQuietLaundryNoise

5.0 out of 5 average rating, 7 reviews

Home in Tabernash

Pole Creek Home 739 - Hot Tub - Views - Game Room

Pole Creek Golf Club Luxury Home 739 / Private Hot Tub / Bunk Room / Great Views / Game Room / Close To Town / Discounted Attractions

HospitalityViewFamilyHot tubBathroomLocationSleep qualityNearbyIndoor spacesCleanlinessAmenities

5.0 out of 5 average rating, 5 reviews

WP Resort Villa 217 - Hot Tub - Bunks - Great View

Lakota Park Luxury Villa 217 / Private Hot Tub / Bunk Room / Great Views / Discounted Attractions / Next Door To Winter Park Resort

HospitalityViewComfortIndoor spacesFamilyGetting aroundHot tubDecorTVAccuracyOutdoor spacesBathroomKitchenHikingLayoutHeatingNearbyParkingWalkabilityConditionLocationSleep qualityAccessAmenities

A modern two-story townhome is showcased with a wooden and stone exterior, featuring large windows that allow natural light to fill the interior. The driveway is flanked by two garage doors, and a simple front porch area is visible, surrounded by natural landscaping.

4.97 out of 5 average rating, 60 reviews

Mountain Villa 1219 - Private Hot Tub - Views

Ascent Mountain Villa 1219 / Private Hot Tub / Great Views / Bunk Room / Fitness Room / Game Room / Discounted Attractions

ViewFamilyLocationKitchenComfortCleanlinessHot tubNearbyIndoor spacesSleep qualityAmenitiesSkiingHospitalityAccuracyBathroomGetting aroundDecorHikingValueCheck-inTVPetsQuietConditionAccessCheckoutOutdoor spacesGrillParksLayoutParkingWalkabilityPoolAir conditioning

A stunning mountain chalet is set among tall trees, featuring a blend of wood and stone architecture. Large windows illuminate the warm interiors, while a spacious deck is visible, showcasing comfortable outdoor seating. Vibrant sunset colors fill the sky, creating a serene ambiance.

4.94 out of 5 average rating, 72 reviews

Ski In Out Chalet 277 - Hot Tub - Great Views

Bridgers Cache Ski In/Out Chalet 277 / Private Hot Tub / Game Room / Great Views / Bunk Room / Discounted Attractions

LocationHospitalityIndoor spacesCleanlinessViewSkiingOutdoor spacesAccuracyFamilyComfortHot tubKitchenAmenitiesWalkabilityGetting aroundConditionSleep qualityQuietHikingLayoutParkingValueCheck-inDecorGrillNearbyNoiseBathroomHeatingLaundryLong stayCheckoutAir conditioningBiking

5.0 out of 5 average rating, 4 reviews

Casa de Montana | Hot Tub | Game Room

Welcome home to Casa de Montaña!

HospitalityConditionAccuracyViewIndoor spacesAccess

5.0 out of 5 average rating, 4 reviews

Trestle House | On Corridor Trail | Hot Tub

Welcome home to Trestle House!

ComfortGetting aroundConditionAccuracyViewHospitalityHot tubKitchenAccessHiking

Popular amenities for Winter Park luxury vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Other great luxury vacation rentals in Winter Park

5.0 out of 5 average rating, 7 reviews

Home in Tabernash

Pole Creek Home 739 - Hot Tub - Views - Game Room

HospitalityViewFamilyHot tubBathroomLocationSleep qualityNearbyIndoor spacesCleanlinessAmenities

4.91 out of 5 average rating, 46 reviews

Downtown WP River Villa 104 - Rooftop Hot Tub

5.0 out of 5 average rating, 5 reviews

WP Resort Villa 217 - Hot Tub - Bunks - Great View

HospitalityViewComfortIndoor spacesFamilyGetting aroundHot tubDecorTVAccuracyOutdoor spacesBathroomKitchenHikingLayoutHeatingNearbyParkingWalkabilityConditionLocationSleep qualityAccessAmenities

4.94 out of 5 average rating, 72 reviews

Ski In Out Chalet 277 - Hot Tub - Great Views

4.97 out of 5 average rating, 60 reviews

Mountain Villa 1219 - Private Hot Tub - Views

4.89 out of 5 average rating, 9 reviews

Canopy House | Large & Luxe | Ski In Ski Out

HospitalitySkiingLocationWalkabilityIndoor spacesCleanlinessGetting aroundHot tubKitchenSleep qualityCheckoutCheck-inParkingFamilyAmenities

4.6 out of 5 average rating, 10 reviews

Riverwalk Luxury Home Steps to River, Town & Trail

HospitalityIndoor spacesLocationWalkabilityGetting aroundNoiseNearbyFamilyCleanlinessAccuracyBathroomSleep qualityKitchenDecorConditionTVViewGrillLayoutComfortAmenities