San Jose Holiday Rentals
House
- Montevideo
- ·
- Ciudad Vieja
- 0.31 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
Hot Tub
Balcony/Terrace
Kitchen
Air Conditioner
R2,279/Night
7 Nights - R15,954
Apartment
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
Pool- Balcony/Terrace
Parking
R814/Night
7 Nights - R5,698
Bed & Breakfast
- Uruguay
- ·
- Montevideo Department
- 3.14 mi to center
9.8Exceptional
(43 Reviews)
1 Bedroom
1 Bath
Fireplace/Heating- Balcony/Terrace
Breakfast- Kitchen
R932/Night
7 Nights - R6,528
Apartment
- Montevideo
- ·
- Punta Carretas
- 0.88 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
237 ft²
Ocean View- Balcony/Terrace
View
Pet Friendly
R2,897/Night
7 Nights - R20,284
House
- Montevideo
- ·
- Buceo
- 0.17 mi to center
10.0Exceptional
(20 Reviews)
1 Bedroom
1 Bath
2 Guests
161.46 ft²
- Pet Friendly
- Kitchen
Designated Smoking Area
R521/Night
7 Nights - R3,647
Apartment
- Montevideo
- ·
- Pocitos
- 0.70 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
366 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
R1,035/Night
7 Nights - R7,244
Apartment
- Montevideo
- ·
- Barrio Sur
- 0.37 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
1 Bath
12 Guests
1184 ft²
- Kitchen
- Parking
- Air Conditioner
Internet
R2,715/Night
7 Nights - R18,998
Apartment
- Montevideo
- ·
- Centro
- 0.08 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,694/Night
7 Nights - R18,868
Apartment
- Montevideo
- ·
- Cordon
- 0.18 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
5 Guests
840 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R2,401/Night
7 Nights - R16,817
Luxury Holiday Rentals in San Jose
Over 815+ Luxury Holiday Rentals in or Near San Jose
New
Apartment
- Montevideo
- ·
- Punta Carretas
- 0.58 mi to center
1 Bedroom
1 Bath
2 Guests
645.83 ft²
- View
- Air Conditioner
- Internet
Accessibility
R92,554/Night
7 Nights - R647,870
RV Rental
- Montevideo
- ·
- Buceo
- 0.61 mi to center
2 Bedrooms
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Internet
R77,278/Night
7 Nights - R540,947
Apartment
- Montevideo
- ·
- Union
- 0.55 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
- Internet
R56,978/Night
7 Nights - R398,845
House
- Colonia
- ·
- Playa Fomento
- 2.86 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
7 Guests
258.33 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
R42,733/Night
7 Nights - R299,134
House
- Ciudad de la Costa
- ·
- Lomas de Solymar
- 0.70 mi to center
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R40,503/Night
7 Nights - R283,522
House
- Montevideo
- ·
- Pocitos
- 0.62 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Internet
Child Friendly
R38,257/Night
7 Nights - R267,796
Apartment
- Montevideo
- ·
- Pocitos
- 0.58 mi to center
9.2Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
322.92 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
R30,084/Night
7 Nights - R210,590
House
- Colonia
- ·
- Playa Santa Ana
- 0.30 mi to center
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R29,791/Night
7 Nights - R208,539
Apartment
- Montevideo
- ·
- Pocitos
- 0.26 mi to center
1 Bedroom
2 Baths
7 Guests
861.11 ft²
- Parking
- Air Conditioner
- Child Friendly
R25,640/Night
7 Nights - R179,480
Top-Rated Holiday Rentals with a Pool in San Jose
Over 142+ The Best Private Villas and Holiday Rentals in San Jose with a Pool
House
- Colonia
- ·
- El Ensueno
- 0.07 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
688.89 ft²
- Pool
- Pet Friendly
- Kitchen
- Parking
R2,442/Night
7 Nights - R17,093
Apartment
- Uruguay
- ·
- Montevideo
- 4.74 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
376.74 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
R977/Night
7 Nights - R6,837
Apartment
- Montevideo
- ·
- Carrasco
- 0.99 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
129.17 ft²
- Oceanfront
Spa- Fireplace/Heating
- Pool
R2,442/Night
7 Nights - R17,093
Apartment
- Montevideo
- ·
- Punta Carretas
- 0.18 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
430.56 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R1,107/Night
7 Nights - R7,749
Ski Chalet
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
258.33 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
R917/Night
7 Nights - R6,414
House
- Uruguay
- ·
- Montevideo Department
- 15.45 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
13 Guests
215.28 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
R4,884/Night
7 Nights - R34,187
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
10 Guests
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,395/Night
7 Nights - R30,768
House
- Uruguay
- ·
- Montevideo Department
- 10.99 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
R1,104/Night
7 Nights - R7,733
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
322.92 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
R798/Night
7 Nights - R5,584
Pet-Friendly Holiday Rentals in San Jose
Over 260+ Pet-Friendly Holiday Rentals in or Near San Jose
Apartment
- Uruguay
- ·
- Montevideo
- 1.85 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
538 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R1,441/Night
7 Nights - R10,093
Apartment
- Uruguay
- ·
- Montevideo Department
- 2.48 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
301.39 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
R700/Night
7 Nights - R4,900
House
- Colonia
- ·
- Nueva Helvecia
- 0.43 mi to center
1 Bedroom
1 Bath
- Balcony/Terrace
- Pet Friendly
- Internet
- Child Friendly
R2,116/Night
7 Nights - R14,814
House
- Colonia
- ·
- Colonia del Sacramento
- 4.28 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R2,917/Night
7 Nights - R20,414
Apartment
- Uruguay
- ·
- Montevideo
- 5.41 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5 Guests
592.02 ft²
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
R733/Night
7 Nights - R5,128
Apartment
- Uruguay
- ·
- Montevideo
- 0.18 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
R1,737/Night
7 Nights - R12,161
Apartment
- Montevideo
- ·
- Pocitos
- 0.65 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
5 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R1,608/Night
7 Nights - R11,249
Apartment
- Montevideo
- ·
- Pocitos
- 0.80 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
3 Guests
754 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
R1,280/Night
7 Nights - R8,954
Apartment
- Uruguay
- ·
- Montevideo
- 5.82 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
R1,029/Night
7 Nights - R7,195
Large Holiday Rentals and Private Villas in San Jose
Over 46+ Large Holiday Rentals and Private Villas in or Near San Jose
Apartment
- Montevideo
- ·
- Carrasco
- 1.28 mi to center
5 Bedrooms
3 Baths
11 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
R10,248/Night
7 Nights - R71,743
Apartment
- Montevideo
- ·
- Punta Carretas
- 0.68 mi to center
9.8Exceptional
(236 Reviews)
4 Bedrooms
4 Baths
16 Guests
618.92 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
R1,237/Night
7 Nights - R8,661
Villa
- Uruguay
- ·
- Montevideo Department
- 13.68 mi to center
4 Bedrooms
4 Baths
12 Guests
- Spa
- Fireplace/Heating
- Pool
- Kitchen
R26,462/Night
7 Nights - R185,227
House
- Colonia
- ·
- Colonia del Sacramento
- 3.33 mi to center
9.5Exceptional
(13 Reviews)
3 Bedrooms
4 Baths
10 Guests
1506.95 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
R3,391/Night
7 Nights - R23,735
Villa
- Uruguay
- ·
- Montevideo Department
- 13.64 mi to center
4 Bedrooms
5 Baths
5 Guests
3444 ft²
Private Pool- Spa
- Fireplace/Heating
- Pool
R26,462/Night
7 Nights - R185,227
Apartment
- Montevideo
- ·
- Ciudad Vieja
- 0.33 mi to center
9.4Exceptional
(1016 Reviews)
12 Bedrooms
1 Bath
3 Guests
279.86 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Parking
R1,084/Night
7 Nights - R7,586
House
- Montevideo
- ·
- Carrasco
- 1.84 mi to center
5 Bedrooms
7 Baths
8 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
R6,154/Night
7 Nights - R43,075
House
- Uruguay
- ·
- Montevideo
- 0.55 mi to center
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
R2,930/Night
7 Nights - R20,512
House
- Montevideo
- ·
- Centro
- 0.19 mi to center
6 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- View
- Kitchen
- Internet
R1,275/Night
7 Nights - R8,921
Wheelchair Accessible Holiday Homes in San Jose
Over 167+ Wheelchair Accessible Holiday Homes in or Near San Jose
Apartment
- Uruguay
- ·
- Montevideo
- 4.96 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
97 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R1,315/Night
7 Nights - R9,198
Apartment
- Montevideo
- ·
- Tres Cruces
- 0.16 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
9 Guests
559.72 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
R1,692/Night
7 Nights - R11,851
Hotel
- Montevideo
- ·
- Carrasco
- 1.58 mi to center
9.8Exceptional
(45 Reviews)
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,637/Night
7 Nights - R18,461
New
Apartment
- Montevideo
- ·
- Ciudad Vieja
- 0.05 mi to center
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
538 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R668/Night
7 Nights - R4,672
Apartment
- Montevideo
- ·
- Tres Cruces
- 0.27 mi to center
9.9Exceptional
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
365.97 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
R1,058/Night
7 Nights - R7,407
Apartment
- Montevideo
- ·
- Punta Carretas
- 0.68 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
377 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R1,091/Night
7 Nights - R7,635
Apartment
- Montevideo
- ·
- Buceo
- 0.96 mi to center
3 Bedrooms
3 Baths
6 Guests
2045 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,747/Night
7 Nights - R33,226
Apartment
- Montevideo
- ·
- Parque Rodo
- 0.49 mi to center
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,381/Night
7 Nights - R16,670
Apartment
- Montevideo
- ·
- Pocitos
- 0.20 mi to center
1 Bedroom
1 Bath
3 Guests
258 ft²
- Ocean View
- View
- Pet Friendly
- Kitchen
R2,035/Night
7 Nights - R14,244
San Jose Private Villas and Holiday Homes Under $200
Over 737+ San Jose Private Villas and Holiday Homes Under $200
Apartment
- Montevideo
- ·
- Pocitos
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
431 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
R1,151/Night
7 Nights - R8,058
Apartment
- Montevideo
- ·
- Punta Carretas
- 0.36 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
5 Guests
861.11 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,359/Night
7 Nights - R16,507
Bed & Breakfast
1 Bedroom
1 Bath
- Balcony/Terrace
- Breakfast
- Kitchen
- Internet
R1,072/Night
7 Nights - R7,505
Apartment
- Montevideo
- ·
- Aguada
- 0.16 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Child Friendly
- Designated Smoking Area
R1,207/Night
7 Nights - R8,449
House
- Montevideo
- ·
- Barrio Sur
- 0.20 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
172.22 ft²
- Balcony/Terrace
- View
- Kitchen
- Parking
R1,140/Night
7 Nights - R7,977
Apartment
- Montevideo
- ·
- Carrasco
- 1.26 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
R1,623/Night
7 Nights - R11,363
Apartment
- Montevideo
- ·
- Pocitos
- 0.35 mi to center
2.0Average
(1 Review)
2 Bedrooms
2 Baths
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R1,534/Night
7 Nights - R10,744
Cottage
- Uruguay
- ·
- Montevideo Department
- 7.59 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R2,963/Night
7 Nights - R20,740
Apartment
- Montevideo
- ·
- Carrasco
- 1.28 mi to center
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,930/Night
7 Nights - R20,512
Instantly Bookable Holiday Homes in San Jose
Over 107+ Instantly Bookable Holiday Homes in or Near San Jose
Apartment
- Uruguay
- ·
- Montevideo
- 5.98 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
592 ft²
- Balcony/Terrace
- Kitchen
- Internet
Security/Safety
R3,728/Night
7 Nights - R26,096
House
- Ciudad de la Costa
- ·
- Lomas de Solymar
- 0.70 mi to center
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R41,480/Night
7 Nights - R290,359
Apartment
- Montevideo
- ·
- Carrasco
- 1.62 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
R11,558/Night
7 Nights - R80,908
House
- Montevideo
- ·
- Carrasco
- 2.08 mi to center
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- View
- Kitchen
R9,361/Night
7 Nights - R65,524
House
- Montevideo
- ·
- Carrasco
- 1.36 mi to center
4 Bedrooms
5 Baths
8 Guests
2691 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R8,844/Night
7 Nights - R61,910
Apartment
- Montevideo
- ·
- Pocitos
- 0.70 mi to center
4 Bedrooms
4 Baths
8 Guests
1830 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R6,858/Night
7 Nights - R48,008
New
Apartment
- Uruguay
- ·
- Montevideo
- 3.01 mi to center
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Internet
- Child Friendly
- Laundry
R3,695/Night
7 Nights - R25,868
House
- Montevideo
- ·
- Carrasco
- 1.26 mi to center
2 Bedrooms
1 Bath
5 Guests
1292 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
R3,516/Night
7 Nights - R24,614
Book a Last Minute Place to Stay in San Jose
About Casai's Private Villas and Holiday Rentals in San Jose
Discover more than 824 vacation rentals available in San Jose. 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 San Jose.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in San Jose, 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 San Jose. On average, places to stay near San Jose offer 350.46 ft², with nightly prices averaging R2,138.
With Casai, finding and comparing holiday rentals in San Jose is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in San Jose
| Type | Count |
|---|---|
| Holiday Apartments | 470 |
| Vacation Homes | 161 |
| Villas | 4 |
| Cottages | 2 |
Use these Quick Filters to Find a Holiday Rental in San Jose
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in San Jose.
Top Attractions Around San Jose, UY
Casai offers a large selection of top attractions around San Jose . Research things to do on your vacation before you visit San Jose.
Other Places to Stay in San Jose, UY
Frequently Asked Questions About San Jose?
What are the top holiday rentals in San Jose?
With numerous options available in San Jose, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in San Jose:
- Hotel Richmond
- FAUNA Montevideo
- Casita La Palmita
- Puerto del Buceo, habitación en Apartamento Compartido
- Stylish Apartment with Balcony Cozy Stay in excellent Location
- Spacious illuminated and unique apartment
- en el corazón del Barrio Sur
- Montevideo al oeste, algo distinto.
- Rambla Bliss Suites - Frente a Playa Pocitos 🌊✨
- La Raíz Piscina Climatizada
How many holiday rentals have private pools in San Jose?
Discover a selection of holiday rentals with private pools near San Jose 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.
- Hermosa Casa Para Disfrutar con Amigos/familiares
- Edificio Lawa Calyptus
- Bungalow with garden, swimming pool, barbecue, pool, in an excellent location!
- Moderno apto en Pocitos con piscina
Which holiday homes in San Jose are best for families?
If you're searching for a family-friendly holiday home in San Jose, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in San Jose:
- Beautiful house to spend with friends and family
- Loft Mitre
- Hotel Montevideo - Leading Hotels of the World
How many Casai.co.za holiday rentals are available in San Jose?
As of 2026, Casai boasts over 824 properties listed in the San Jose area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in San Jose.
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