Condo
10.0(91 Reviews)
3 Bedrooms
6 Guests
Hot Tub
Parking
Pool
Spa
R17,036/Night
7 Nights - R119,253
Aspen Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Aspen
10.0
House
10.0(5 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
Skiing
R14,939/Night
7 Nights - R104,579
R9,859/Night
7 Nights - R69,010
House
10.0(85 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Balcony/Terrace
R21,565/Night
7 Nights - R150,960
R12,218/Night
7 Nights - R85,532
Condo
10.0(82 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R16,471/Night
7 Nights - R115,291
House
10.0(77 Reviews)
6 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
Kitchen
R15,218/Night
7 Nights - R106,527
House
10.0(75 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R7,711/Night
7 Nights - R53,973
Condo
10.0(73 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
Internet
R21,474/Night
7 Nights - R150,316
Luxury Holiday Rentals in Aspen
Over 2853+ Luxury Holiday Rentals in or Near Aspen
New
Condo
3 Bedrooms
8 Guests
Child Friendly
Security/Safety
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New
House
6 Bedrooms
14 Guests
- Kitchen
- Child Friendly
- Security/Safety
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House
6 Bedrooms
14 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
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House
5 Bedrooms
10 Guests
- Kitchen
Air Conditioner- Internet
- Child Friendly
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House
6 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
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House
6 Bedrooms
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
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Top-Rated Holiday Rentals with a Pool in Aspen
Over 1528+ The Best Private Villas and Holiday Rentals in Aspen with a Pool
![The Aspen Mountain Residences [Formerly Hyatt Grand Aspen] at Owner Direct Rates](https://imgservice.casai.co.za/640x287/the-aspen-mountain-residen-us-aspen-ha-321443179-0.jpg)
Apartment
10.0(82 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R10,815/Night
7 Nights - R75,711
Condo
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R11,454/Night
7 Nights - R80,184
Condo
10.0(63 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R11,776/Night
7 Nights - R82,429
Condo
10.0(60 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R7,931/Night
7 Nights - R55,508
Apartment
10.0(51 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R18,196/Night
7 Nights - R127,373
Condo
10.0(48 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R14,898/Night
7 Nights - R104,282
Apartment
10.0(46 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R10,815/Night
7 Nights - R75,711
Condo
10.0(42 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
R22,227/Night
7 Nights - R155,581
House
10.0(41 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R28,933/Night
7 Nights - R202,523
Pet-Friendly Holiday Rentals in Aspen
Over 329+ Pet-Friendly Holiday Rentals in or Near Aspen
Condo
10.0(71 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R16,998/Night
7 Nights - R118,988
R18,142/Night
7 Nights - R126,994
R7,802/Night
7 Nights - R54,617
House
10.0(61 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
View
R9,694/Night
7 Nights - R67,854
R11,962/Night
7 Nights - R83,733
Condo
10.0(59 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
R13,650/Night
7 Nights - R95,551
House
10.0(30 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R15,221/Night
7 Nights - R106,543
House
10.0(26 Reviews)
7 Bedrooms
18 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R32,903/Night
7 Nights - R230,318
House
10.0(25 Reviews)
6 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
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Large Holiday Rentals and Private Villas in Aspen
Over 342+ Large Holiday Rentals and Private Villas in or Near Aspen
House
10.0(54 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
R34,043/Night
7 Nights - R238,307
House
10.0(1 Review)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R43,228/Night
7 Nights - R302,596
House
10.0(33 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R40,801/Night
7 Nights - R285,612
House
10.0(1 Review)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
R14,734/Night
7 Nights - R103,143
Apartment
10.0(30 Reviews)
3 Bedrooms
11 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R9,332/Night
7 Nights - R65,329
Boat Rental
10.0(15 Reviews)
5 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R58,196/Night
7 Nights - R407,373
House
10.0(9 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
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House
10.0(9 Reviews)
6 Bedrooms
14 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R93,363/Night
7 Nights - R653,537
House
10.0(9 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R53,269/Night
7 Nights - R372,877
Wheelchair Accessible Holiday Homes in Aspen
Over 880+ Wheelchair Accessible Holiday Homes in or Near Aspen
Condo
10.0(50 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R23,489/Night
7 Nights - R164,412
R12,639/Night
7 Nights - R88,470
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Condo
10.0(39 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Skiing
R24,500/Night
7 Nights - R171,493
Apartment
9.3(3 Reviews)
3 Bedrooms
5 Guests
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
R9,199/Night
7 Nights - R64,388
Condo
10.0(39 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R19,388/Night
7 Nights - R135,709
Condo
10.0(38 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R14,185/Night
7 Nights - R99,297
Condo
10.0(34 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
Breakfast- Parking
- Pool
R9,042/Night
7 Nights - R63,299
Condo
10.0(26 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R21,489/Night
7 Nights - R150,432
Aspen Private Villas and Holiday Homes Under $200
Over 15+ Aspen Private Villas and Holiday Homes Under $200
Condo
9.6(33 Reviews)
1 Bedroom
2 Guests
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
R1,832/Night
7 Nights - R12,825
Cabin
8.8(794 Reviews)
12 Bedrooms
33 Guests
- Parking
- Pool
- Skiing
- Balcony/Terrace
R3,219/Night
7 Nights - R22,530
R2,401/Night
7 Nights - R16,803
Condo
9.4(21 Reviews)
1 Bedroom
2 Guests
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
R2,475/Night
7 Nights - R17,314
House
7.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Internet
Bedding/Linens
Transportation/Shuttle
R2,839/Night
7 Nights - R19,873
Condo
9.0(7 Reviews)
1 Bedroom
2 Guests
- Parking
- Skiing
- Kitchen
- Internet
R1,946/Night
7 Nights - R13,617
House
1 Bedroom
1 Guest
- Balcony/Terrace
- Kitchen
- Child Friendly
- Security/Safety
R3,054/Night
7 Nights - R21,375
New
Condo
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R1,777/Night
7 Nights - R12,445
Condo
4.9(11 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Internet
- Child Friendly
R3,301/Night
7 Nights - R23,108
Instantly Bookable Holiday Homes in Aspen
Over 1268+ Instantly Bookable Holiday Homes in or Near Aspen
Condo
Aspen Winter Escape! 3 Block to Aspen Mountain, Fireplace, Views, Balcony, WD, Parking, Walk to Town
10.0(45 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R12,301/Night
7 Nights - R86,109
Condo
9.8(25 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R11,818/Night
7 Nights - R82,726
Condo
10.0(38 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R17,716/Night
7 Nights - R124,006
Condo
10.0(36 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R8,654/Night
7 Nights - R60,575
Condo
10.0(35 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
R20,918/Night
7 Nights - R146,421
Condo
10.0(35 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R12,301/Night
7 Nights - R86,109
Cabin
10.0(35 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
R6,702/Night
7 Nights - R46,909
Condo
10.0(34 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R8,548/Night
7 Nights - R59,833
Condo
Multi-Level Townhome in the Heart of Aspen! FP, WD, Pool & Hot Tub, Parking, 7 beds, 2nd Living Room
10.0(32 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R16,367/Night
7 Nights - R114,565
Book a Last Minute Place to Stay in Aspen
About Casai's Private Villas and Holiday Rentals in Aspen
Discover more than 2862 vacation rentals available in Aspen. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Aspen.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Aspen, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Aspen. On average, places to stay near Aspen offer 769.3 ft², with nightly prices averaging R40,105.
With Casai, finding and comparing holiday rentals in Aspen is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Aspen, CO
There are 2862 Aspen, CO Holiday Rentals
- Prices for a holiday home in Aspen start at R1,777
- Top rated vacation home in Aspen is PENTHOUSE "CHATEAU ROARING FORK", AC, ALL DAY SUN, VIEWS-AVAILABLE FOOD-WINE
- Most popular short term in Aspen is The Inn at Aspen
- Cheapest place to stay in Aspen is Updated Aspen Core Studio on River!
- Most expensive holiday rental in Aspen is 3 BDR Condo, Aspen Core, Few Block to Gondola
Recently Booked Holiday Rentals in Aspen
- PENTHOUSE "CHATEAU ROARING FORK", AC, ALL DAY SUN, VIEWS-AVAILABLE FOOD-WINE
- Central AC, Updated 4 BR, 4-5 BA Townhouse, Pool
- Aspen Mountain Luxury Getaway - 1BR Residence w/ Fireplace & Private Pool
- Deluxe private townhome minutes walk to Aspen Mountain skiing and downtown!
- Aspen Alps Apartment #402
Frequently Asked Questions About Aspen?
What are the top holiday rentals in Aspen?
With numerous options available in Aspen, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Aspen:
- PENTHOUSE "CHATEAU ROARING FORK", AC, ALL DAY SUN, VIEWS-AVAILABLE FOOD-WINE
- Deluxe private townhome minutes walk to Aspen Mountain skiing and downtown!
- Gondola Plaza adjacent with treehouse views over Aspen
- The Aspen Mountain Residences [Formerly Hyatt Grand Aspen] at Owner Direct Rates
- Aspen Riverhouse-Riverfront Family Vacation
- Charming 3 Bedroom family house with hot tub on 2 acres panoramic views
- PERFECTLY LOCATED ASPEN CONDO! Walking distance to everything in Aspen
- 3 Bed/3 Bath In Town Aspen Luxury King & 2 Queen Bed W/D AC Parking Balcony Wifi
- Aspen Condo 1.5 Blocks to Town. Balcony. Outdoor Pool. Sleeping Den w/Sofa Bed, 3 Bathrooms, Gas FP
- Beautiful modern Aspen Core Condo- 2 Bed 2 Bath, AC, pool and hot tub
How many holiday rentals have private pools in Aspen?
Discover a selection of holiday rentals with private pools near Aspen with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Aspen are best for families?
If you're searching for a family-friendly holiday home in Aspen, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Aspen:
How many Casai.co.za holiday rentals are available in Aspen?
As of 2026, Casai boasts over 2862 properties listed in the Aspen area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Aspen.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Vacation Rentals in Aspen, Colorado | 1104 |
| West End Vacation Rentals in Aspen, Colorado | 85 |
| Mountain Valley Vacation Rentals in Aspen, Colorado | 2513 |
| Red Mountain Vacation Rentals in Aspen, Colorado | 2624 |
| Brush Creek Village Vacation Rentals in Aspen, Colorado | 168 |
| Knollwood Vacation Rentals in Aspen, Colorado | 2623 |
| Starwood Vacation Rentals in Aspen, Colorado | 184 |
| Meadowood Vacation Rentals in Aspen, Colorado | 2638 |
| Oklahoma Flats Vacation Rentals in Aspen, Colorado | 2632 |
| Maroon Creek Vacation Rentals in Aspen, Colorado | 2593 |
| North Forty Vacation Rentals in Aspen, Colorado | 719 |
