Oakland Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Oakland, Pittsburgh, Pennsylvania, USA

Luxury Condo Near Shady side Hospital | King Bed
Apartment
Luxury Condo Near Shady side Hospital | King Bed
From US $283 per night
10.0 (5 Reviews)
2 Bedrooms 6 Guests
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461 Melwood Suites Unit 101 2Bed/2Bath
Apartment
461 Melwood Suites Unit 101 2Bed/2Bath
From US $304 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
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NEW Gorgeous 4bd near universities Hot tub Games
House
NEW Gorgeous 4bd near universities Hot tub Games
From US $400 per night
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10.0 (1 Review)
4 Bedrooms 10 Guests
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461 Melwood Suites Unit 102 Studio
Apartment
461 Melwood Suites Unit 102 Studio
From US $267 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Serene Retreat in the Heart of Pittsburgh Oakland
Apartment
Serene Retreat in the Heart of Pittsburgh Oakland
From US $74 per night
10.0 (1 Review)
5 Bedrooms 2 Guests
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Melwood Suites Unit 103 Studio
Apartment
Melwood Suites Unit 103 Studio
From US $262 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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NEW Gorgeous 4bd near universities Hot tub + Games
House
NEW Gorgeous 4bd near universities Hot tub + Games
From US $409 per night
8.8 (5 Reviews)
4 Bedrooms 10 Guests
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3E-*New* 5 min to UPMC Shadyside, sleeps 4
Apartment
3E-*New* 5 min to UPMC Shadyside, sleeps 4
From US $244 per night
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9.9 (13 Reviews)
1 Bedroom 4 Guests
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Downtown Victorian Mansion
House
Downtown Victorian Mansion
From US $1,127 per night
2.0 (2 Reviews)
8 Bedrooms 29 Guests
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3E-*New* Apartment -5 min from Downtown, sleeps 4
Apartment
3E-*New* Apartment -5 min from Downtown, sleeps 4
From US $229 per night
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9.8 (17 Reviews)
1 Bedroom 4 Guests
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New Loft 3 min to Childrens Hospital Sleeps 4
Apartment
New Loft 3 min to Childrens Hospital Sleeps 4
From US $140 per night
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9.5 (4 Reviews)
1 Bedroom 4 Guests
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New 3 Story home w/11 beds! | Close to Pitt & CMU!
Apartment
3 Story home w/11 beds! | Close to Pitt & CMU!
From US $474 per night
New
7 Bedrooms 16 Guests
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3E-Spacious 2 bedroom in Oakland, sleeps 8
Apartment
3E-Spacious 2 bedroom in Oakland, sleeps 8
From US $380 per night
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9.3 (29 Reviews)
2 Bedrooms 8 Guests
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5 min to UPMC Shadyside Oakland East Liberty, sleeps 6 unit 304
Apartment
5 min to UPMC Shadyside Oakland East Liberty, sleeps 6 unit 304
From US $216 per night
10.0 (24 Reviews)
2 Bedrooms 6 Guests
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Industrial Loft 5 min to UPMC Shadyside CMU Pitt, sleeps 4
Apartment
Industrial Loft 5 min to UPMC Shadyside CMU Pitt, sleeps 4
From US $256 per night
10.0 (5 Reviews)
1 Bedroom 4 Guests
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3E-Spacious close to PITT/CMU/Carlow, Sleeps 4
Apartment
3E-Spacious close to PITT/CMU/Carlow, Sleeps 4
From US $192 per night
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9.2 (31 Reviews)
1 Bedroom 4 Guests
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*New* *Unique* 2b/2b sleeps 8 in North Oakland!
Apartment
*New* *Unique* 2b/2b sleeps 8 in North Oakland!
From US $230 per night
10.0 (4 Reviews)
2 Bedrooms 8 Guests
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3E-*New* Apt -5 min from Downtown, 3E, Sleeps 6
Apartment
3E-*New* Apt -5 min from Downtown, 3E, Sleeps 6
From US $259 per night
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9.1 (21 Reviews)
2 Bedrooms 6 Guests
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Charming studio with WiFi and AC in vibrant Pittsburgh
Apartment
Charming studio with WiFi and AC in vibrant Pittsburgh
From US $149 per night
10.0 (3 Reviews)
1 Bedroom 2 Guests
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3E-*Renovated* 5 min to UPMC Shadyside, sleeps 6
Apartment
3E-*Renovated* 5 min to UPMC Shadyside, sleeps 6
From US $221 per night
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9.0 (22 Reviews)
2 Bedrooms 6 Guests
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Industr Loft 5min Shadyside East Liberty Oakland 6
Apartment
Industr Loft 5min Shadyside East Liberty Oakland 6
From US $252 per night
9.8 (40 Reviews)
2 Bedrooms 6 Guests
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3E *New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12!
Apartment
3E *New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12!
From US $827 per night
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9.0 (12 Reviews)
3 Bedrooms 12 Guests
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*New* Loft 3 min to CMU, Pitt Sleeps 4
Apartment
*New* Loft 3 min to CMU, Pitt Sleeps 4
From US $151 per night
9.8 (14 Reviews)
1 Bedroom 4 Guests
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*New* Loft 3 min to Local hospitals Sleeps 4
Apartment
*New* Loft 3 min to Local hospitals Sleeps 4
From US $147 per night
9.8 (9 Reviews)
1 Bedroom 4 Guests
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3E-*New* Apt 10 min to Children’s Hospital, slps 4
Apartment
3E-*New* Apt 10 min to Children’s Hospital, slps 4
From US $202 per night
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8.9 (13 Reviews)
1 Bedroom 4 Guests
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Cozy! Micro Loft apartment Shadyside, sleeps 1
Apartment
Cozy! Micro Loft apartment Shadyside, sleeps 1
From US $140 per night
9.8 (9 Reviews)
1 Bedroom 1 Guest
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Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
Apartment
Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
From US $218 per night
9.6 (43 Reviews)
2 Bedrooms 6 Guests
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Spacious Loft 2 bedroom in N Oakland 400, sleeps 8
Apartment
Spacious Loft 2 bedroom in N Oakland 400, sleeps 8
From US $272 per night
9.6 (30 Reviews)
2 Bedrooms 8 Guests
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*New* Loft 7 min to Acrisure Stadium Sleeps 4
Apartment
*New* Loft 7 min to Acrisure Stadium Sleeps 4
From US $164 per night
9.6 (7 Reviews)
1 Bedroom 4 Guests
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Hillman Cancer Center/Children Hospitals Sleeps 6
Apartment
Hillman Cancer Center/Children Hospitals Sleeps 6
From US $209 per night
9.4 (14 Reviews)
2 Bedrooms 6 Guests
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Ind Loft Children's Hospital Shadyside Oakland 4
Apartment
Ind Loft Children's Hospital Shadyside Oakland 4
From US $212 per night
9.0 (10 Reviews)
1 Bedroom 4 Guests
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Cozy! Micro Loft apartment! in N Oakland, sleeps 1
Apartment
Cozy! Micro Loft apartment! in N Oakland, sleeps 1
From US $157 per night
9.0 (2 Reviews)
1 Bedroom 1 Guest
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*New* Loft 3 min to Childrens Hospital Sleeps 4
Apartment
*New* Loft 3 min to Childrens Hospital Sleeps 4
From US $195 per night
8.8 (5 Reviews)
1 Bedroom 4 Guests
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3E-Cozy! Micro apartment! in Oakland, sleeps 1
Apartment
3E-Cozy! Micro apartment! in Oakland, sleeps 1
From US $168 per night
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8.7 (24 Reviews)
1 Bedroom 1 Guest
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424 Gold Way-Apt. 302
Apartment
424 Gold Way-Apt. 302
From US $184 per night
|
9.8 (22 Reviews)
1 Bedroom 2 Guests
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3E - *Renovated* 3 min to Hillman Cancer Center Sleeps 6
Apartment
3E - *Renovated* 3 min to Hillman Cancer Center Sleeps 6
From US $250 per night
|
8.7 (15 Reviews)
2 Bedrooms 6 Guests
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Melwood Suites Unit 107 Studio
Apartment
Melwood Suites Unit 107 Studio
From US $131 per night
9.6 (33 Reviews)
1 Bedroom 2 Guests
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424-Apt. 403
Apartment
424-Apt. 403
From US $186 per night
|
9.6 (31 Reviews)
1 Bedroom 2 Guests
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New Loft 5 min to PPG or Convention center Sleeps 4
Apartment
New Loft 5 min to PPG or Convention center Sleeps 4
From US $104 per night
8.5 (4 Reviews)
1 Bedroom 4 Guests
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424-Apt. 405
Apartment
424-Apt. 405
From US $311 per night
|
9.4 (12 Reviews)
1 Bedroom 2 Guests
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3E-*New* 3 min to Hillman Cancer Center, Sleeps 6
Apartment
3E-*New* 3 min to Hillman Cancer Center, Sleeps 6
From US $241 per night
|
8.3 (22 Reviews)
2 Bedrooms 5 Guests
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Melwood Suites Unit 106 Studio
Apartment
Melwood Suites Unit 106 Studio
From US $175 per night
9.4 (3 Reviews)
1 Bedroom 2 Guests
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3E-Cozy! Micro apartment minutes from Shadyside, sleeps 1
Apartment
3E-Cozy! Micro apartment minutes from Shadyside, sleeps 1
From US $169 per night
|
8.1 (36 Reviews)
1 Bedroom 1 Guest
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424-Apt 304
Apartment
424-Apt 304
From US $186 per night
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9.2 (12 Reviews)
1 Bedroom 2 Guests
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424 Gold Way-Apt 402, 2 Bed/1Bath
Apartment
424 Gold Way-Apt 402, 2 Bed/1Bath
From US $227 per night
|
9.0 (10 Reviews)
1 Bedroom 2 Guests
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424-Apt. 406
Apartment
424-Apt. 406
From US $198 per night
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9.0 (6 Reviews)
1 Bedroom 2 Guests
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Cato Spacious 5BR Home Oakland Pittsburgh
Apartment
Cato Spacious 5BR Home Oakland Pittsburgh
From US $194 per night
New
5 Bedrooms 10 Guests
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424 Gold Way- 3Bed/2Bath Apartment
Apartment
424 Gold Way- 3Bed/2Bath Apartment
From US $536 per night
|
9.0 (4 Reviews)
1 Bedroom 2 Guests
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The Oaklander Hotel, Autograph Collection
Hotel
The Oaklander Hotel, Autograph Collection
From US $284 per night
|
8.5 (125 Reviews)
166 Bedrooms 36 Guests
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424 Gold Way-Apt. 303
Apartment
424 Gold Way-Apt. 303
From US $184 per night
|
8.8 (16 Reviews)
1 Bedroom 2 Guests
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Residence Inn by Marriott Pittsburgh Oakland/University Place
Hotel
Residence Inn by Marriott Pittsburgh Oakland/University Place
From US $220 per night
|
8.3 (266 Reviews)
144 Bedrooms 30 Guests
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424-Apt. 400
Apartment
424-Apt. 400
From US $260 per night
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8.0 (8 Reviews)
1 Bedroom 2 Guests
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Hotel Indigo Pittsburgh University - Oakland by IHG
Hotel
Hotel Indigo Pittsburgh University - Oakland by IHG
From US $186 per night
|
8.3 (234 Reviews)
124 Bedrooms 44 Guests
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Courtyard by Marriott Pittsburgh University Center
Hotel
Courtyard by Marriott Pittsburgh University Center
From US $208 per night
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8.0 (947 Reviews)
253 Bedrooms 60 Guests
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Melwood Suites Unit 104 Studio
Apartment
Melwood Suites Unit 104 Studio
From US $187 per night
8.0 (1 Review)
1 Bedroom 2 Guests
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Melwood Suites Unit 105 Studio
Apartment
Melwood Suites Unit 105 Studio
From US $273 per night
New
1 Bedroom 2 Guests
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Residence Inn Pittsburgh Oakland/University Place
Hotel
Residence Inn Pittsburgh Oakland/University Place
From US $154 per night
|
9.2 (877 Reviews)
1 Bedroom 2 Guests
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About Oakland Vacation Rentals

Explore over 101 vacation rentals in Oakland with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Oakland for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Oakland. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Oakland tailored to your preferences. On average, these rentals offer 835.37 ft² of space, and are priced at an average of US $270 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Oakland at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Other Places to Stay in Oakland, PA


Petersen Events Center 2,012 Properties
UPMC Presbyterian Hospital 2,010 Properties
UPMC Montefiore 2,010 Properties
University of Pittsburgh Medical Center 2,003 Properties
University of Pittsburgh 1,991 Properties
The Nationality Rooms 1,991 Properties
Pittsburgh Playhouse 1,966 Properties
UPMC Magee-Womens Hospital 1,958 Properties
Soldiers and Sailors Memorial Hall and Museum 1,891 Properties
South Oakland 1,851 Properties
Cathedral of Learning 1,837 Properties
North Oakland 103 Properties

Frequently Asked Questions About Oakland?

What are the top vacation rentals in Oakland?

How many SunSkiResorts vacation rentals or resorts are available in Oakland?

Discover the ideal vacation rental in Oakland with SunSki Resorts™. We provide an extensive selection of over 101 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Oakland.

Nearby Neighborhood (4)

Neighborhood Property Count
North Oakland Vacation Rentals in Pittsburgh, Pennsylvania 103
South Oakland Vacation Rentals in Pittsburgh, Pennsylvania 1851
Bluff Vacation Rentals in Pittsburgh, Pennsylvania 1827
Squirrel Hill South Vacation Rentals in Pittsburgh, Pennsylvania 784

There are 101 Oakland, PA Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Oakland