San Jose Holiday Rentals
10.0
Exceptional
(33 Reviews)
- Montevideo
- Ciudad Vieja
- 0.22 mi to center
592 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $80/Night
For 7 Nights US $560
10.0
Exceptional
(57 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Hot Tub
- Pool
- Balcony/Terrace
US $50/Night
For 7 Nights US $350
9.8
Exceptional
(43 Reviews)
- Uruguay
- Montevideo Department
- 3.14 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $62/Night
For 7 Nights US $431
10.0
Exceptional
(7 Reviews)
- Montevideo
- Ciudad Vieja
- 0.31 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- Kitchen
US $108/Night
For 7 Nights US $753
10.0
Exceptional
(20 Reviews)
161.46 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- Pet Friendly
- Kitchen
- Designated Smoking Area
US $32/Night
For 7 Nights US $224
10.0
Exceptional
(4 Reviews)
- Montevideo
- Pocitos
- 0.70 mi to center
366 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
US $64/Night
For 7 Nights US $445
10.0
Exceptional
(3 Reviews)
- Montevideo
- Punta Carretas
- 0.88 mi to center
237 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- Balcony/Terrace
- View
US $62/Night
For 7 Nights US $434
10.0
Exceptional
(2 Reviews)
- Montevideo
- Barrio Sur
- 0.37 mi to center
1184 ft²
12 Guests
4 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Kitchen
- Parking
- Air Conditioner
US $214/Night
For 7 Nights US $1,498
10.0
Exceptional
(2 Reviews)
- Montevideo
- Centro
- 0.08 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $135/Night
For 7 Nights US $947
Luxury Holiday Rentals in San Jose
Over 858+ Luxury Holiday Rentals in or Near San Jose
New
- Montevideo
- Buceo
- 0.61 mi to center
2 Guests
2 Bedrooms
1 Bathroom
Ocean View
RV Rental
- Ocean View
- Balcony/Terrace
- View
US $4,023/Night
For 7 Nights US $28,160
New
1614.59 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $3,800/Night
For 7 Nights US $26,600
New
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
US $3,500/Night
For 7 Nights US $24,500
10.0
Exceptional
(1 Review)
258.33 ft²
7 Guests
2 Bedrooms
1 Bathroom
House
- View
- Pet Friendly
- Parking
US $2,625/Night
For 7 Nights US $18,375
New
- Ciudad de la Costa
- Lomas de Solymar
- 0.70 mi to center
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $2,491/Night
For 7 Nights US $17,437
New
2 Guests
1 Bedroom
1 Bathroom
House
- Balcony/Terrace
- Internet
- Child Friendly
US $2,350/Night
For 7 Nights US $16,450
New
- Montevideo
- Tres Cruces
- 0.17 mi to center
1614.59 ft²
7 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Balcony/Terrace
- Air Conditioner
- Internet
US $2,100/Night
For 7 Nights US $14,700
New
- Colonia
- Playa Santa Ana
- 0.30 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $2,037/Night
For 7 Nights US $14,259
New
- Montevideo
- Carrasco
- 2.08 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- View
US $2,019/Night
For 7 Nights US $14,133
Top-Rated Holiday Rentals with a Pool in San Jose
Over 153+ The Best Private Villas and Holiday Rentals in San Jose with a Pool
10.0
Exceptional
(4 Reviews)
688.89 ft²
4 Guests
2 Bedrooms
1 Bathroom
House
- Pool
- Pet Friendly
- Kitchen
US $150/Night
For 7 Nights US $1,050
10.0
Exceptional
(3 Reviews)
- Canelones
- San Jacinto
- 1.46 mi to center
391.81 ft²
20 Guests
6 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $113/Night
For 7 Nights US $788
10.0
Exceptional
(3 Reviews)
376.74 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $60/Night
For 7 Nights US $420
10.0
Exceptional
(2 Reviews)
- Montevideo
- Carrasco
- 0.99 mi to center
129.17 ft²
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Oceanfront
- Spa
- Fireplace/Heating
US $150/Night
For 7 Nights US $1,050
10.0
Exceptional
(2 Reviews)
430.56 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Oceanfront
- Pool
- Ocean View
US $68/Night
For 7 Nights US $476
10.0
Exceptional
(2 Reviews)
258.33 ft²
3 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Ski Chalet
- Private Beach
- Oceanfront
- Fireplace/Heating
US $56/Night
For 7 Nights US $394
10.0
Exceptional
(1 Review)
215.28 ft²
13 Guests
5 Bedrooms
4 Bathrooms
House
- Pool
- Balcony/Terrace
- Pet Friendly
US $300/Night
For 7 Nights US $2,100
10.0
Exceptional
(1 Review)
10 Guests
4 Bedrooms
2 Bathrooms
House
- Pool
- Balcony/Terrace
- Pet Friendly
US $270/Night
For 7 Nights US $1,890
10.0
Exceptional
(1 Review)
- Montevideo
- Pocitos
- 0.53 mi to center
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
US $156/Night
For 7 Nights US $1,092
Pet-Friendly Holiday Rentals in San Jose
Over 272+ Pet-Friendly Holiday Rentals in or Near San Jose
10.0
Exceptional
(2 Reviews)
- Uruguay
- Montevideo
- 1.85 mi to center
538 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $82/Night
For 7 Nights US $574
10.0
Exceptional
(4 Reviews)
- Uruguay
- Montevideo
- 10.62 mi to center
107.64 ft²
5 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $85/Night
For 7 Nights US $595
New
- Colonia
- Nueva Helvecia
- 0.43 mi to center
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Internet
US $130/Night
For 7 Nights US $910
10.0
Exceptional
(1 Review)
- Colonia
- Colonia del Sacramento
- 4.28 mi to center
9 Guests
4 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $124/Night
For 7 Nights US $869
10.0
Exceptional
(3 Reviews)
- Uruguay
- Montevideo
- 4.87 mi to center
861.11 ft²
4 Guests
1 Bedroom
1 Bathroom
Pet Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $89/Night
For 7 Nights US $623
10.0
Exceptional
(1 Review)
- Uruguay
- Montevideo
- 0.18 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $108/Night
For 7 Nights US $756
10.0
Exceptional
(1 Review)
- Montevideo
- Pocitos
- 0.65 mi to center
969 ft²
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $96/Night
For 7 Nights US $669
10.0
Exceptional
(1 Review)
- Montevideo
- Pocitos
- 0.80 mi to center
754 ft²
3 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Parking
US $77/Night
For 7 Nights US $536
8.0
Excellent
(1 Review)
- Montevideo
- Pocitos
- 0.73 mi to center
915 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $127/Night
For 7 Nights US $889
Large Holiday Rentals and Private Villas in San Jose
Over 52+ Large Holiday Rentals and Private Villas in or Near San Jose
New
- Montevideo
- Carrasco
- 1.28 mi to center
11 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $496/Night
For 7 Nights US $3,472
9.8
Exceptional
(236 Reviews)
618.92 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
US $76/Night
For 7 Nights US $532
New
- Uruguay
- Montevideo Department
- 13.68 mi to center
12 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Spa
- Fireplace/Heating
- Pool
US $1,625/Night
For 7 Nights US $11,378
9.5
Exceptional
(13 Reviews)
- Colonia
- Colonia del Sacramento
- 3.33 mi to center
1506.95 ft²
10 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Pet Friendly
US $208/Night
For 7 Nights US $1,458
New
- Uruguay
- Montevideo Department
- 13.64 mi to center
3444 ft²
5 Guests
4 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Spa
- Fireplace/Heating
US $1,625/Night
For 7 Nights US $11,378
9.4
Exceptional
(1016 Reviews)
- Montevideo
- Ciudad Vieja
- 0.33 mi to center
279.86 ft²
3 Guests
12 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $67/Night
For 7 Nights US $466
New
- Montevideo
- Carrasco
- 1.84 mi to center
8 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
US $378/Night
For 7 Nights US $2,646
New
- Uruguay
- Montevideo
- 0.55 mi to center
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $180/Night
For 7 Nights US $1,260
New
- Montevideo
- Centro
- 0.19 mi to center
8 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- View
- Kitchen
US $78/Night
For 7 Nights US $548
Wheelchair Accessible Holiday Homes in San Jose
Over 171+ Wheelchair Accessible Holiday Homes in or Near San Jose
10.0
Exceptional
(2 Reviews)
- Montevideo
- Cordon
- 0.18 mi to center
840 ft²
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $112/Night
For 7 Nights US $786
10.0
Exceptional
(10 Reviews)
- Montevideo
- Cordon
- 0.70 mi to center
559.72 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $75/Night
For 7 Nights US $525
9.8
Exceptional
(43 Reviews)
- Montevideo
- Carrasco
- 1.58 mi to center
1 Bathroom
Couples Retreat
Hotel
- Spa
- Fireplace/Heating
- Pool
US $177/Night
For 7 Nights US $1,239
10.0
Exceptional
(1 Review)
- Montevideo
- Punta Carretas
- 0.51 mi to center
301 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $71/Night
For 7 Nights US $498
10.0
Exceptional
(2 Reviews)
559.72 ft²
9 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $104/Night
For 7 Nights US $728
9.0
Exceptional
(2 Reviews)
- Uruguay
- Montevideo
- 4.96 mi to center
420 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $64/Night
For 7 Nights US $450
9.0
Exceptional
(2 Reviews)
- Montevideo
- Ciudad Vieja
- 0.05 mi to center
538 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $38/Night
For 7 Nights US $266
6.0
Good
(1 Review)
- Montevideo
- Punta Carretas
- 0.68 mi to center
377 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $67/Night
For 7 Nights US $469
New
- Montevideo
- Buceo
- 0.96 mi to center
2045 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $288/Night
For 7 Nights US $2,018
San Jose Private Villas and Holiday Homes Under $200
Over 778+ San Jose Private Villas and Holiday Homes Under $200
10.0
Exceptional
(2 Reviews)
- Montevideo
- Pocitos
- 0.17 mi to center
431 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $71/Night
For 7 Nights US $495
10.0
Exceptional
(9 Reviews)
- Montevideo
- Punta Carretas
- 0.36 mi to center
861.11 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $145/Night
For 7 Nights US $1,014
New
- Canelones
- Las Piedras
- 1.45 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $47/Night
For 7 Nights US $329
10.0
Exceptional
(1 Review)
- Uruguay
- Montevideo
- 5.98 mi to center
592 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Internet
US $94/Night
For 7 Nights US $655
10.0
Exceptional
(6 Reviews)
- Montevideo
- Aguada
- 0.55 mi to center
1237.85 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Air Conditioner
- Internet
- Child Friendly
US $72/Night
For 7 Nights US $506
10.0
Exceptional
(1 Review)
- Montevideo
- Aguada
- 0.16 mi to center
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Parking
- Child Friendly
- Designated Smoking Area
US $74/Night
For 7 Nights US $515
9.0
Exceptional
(4 Reviews)
- Montevideo
- Punta Carretas
- 0.13 mi to center
344 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $52/Night
For 7 Nights US $361
8.0
Excellent
(1 Review)
- Uruguay
- Montevideo
- 5.82 mi to center
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $67/Night
For 7 Nights US $470
6.0
Good
(1 Review)
- Montevideo
- Aguada
- 0.28 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $80/Night
For 7 Nights US $560
Instantly Bookable Holiday Homes in San Jose
Over 112+ Instantly Bookable Holiday Homes in or Near San Jose
2.0
Average
(1 Review)
- Montevideo
- Carrasco
- 1.26 mi to center
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- Balcony/Terrace
- View
US $87/Night
For 7 Nights US $609
New
- Ciudad de la Costa
- Lomas de Solymar
- 0.70 mi to center
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $2,548/Night
For 7 Nights US $17,836
2.0
Average
(1 Review)
- Montevideo
- Pocitos
- 0.35 mi to center
2 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $75/Night
For 7 Nights US $527
New
- Montevideo
- Carrasco
- 1.62 mi to center
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $810/Night
For 7 Nights US $5,670
New
- Montevideo
- Carrasco
- 1.36 mi to center
2691 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $543/Night
For 7 Nights US $3,803
New
- Montevideo
- Pocitos
- 0.70 mi to center
1830 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $518/Night
For 7 Nights US $3,628
New
- Uruguay
- Montevideo Department
- 4.54 mi to center
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Ski Chalet
- Fireplace/Heating
- Pool
- Pet Friendly
US $513/Night
For 7 Nights US $3,588
New
- Uruguay
- Montevideo Department
- 7.83 mi to center
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $475/Night
For 7 Nights US $3,325
Book a Last Minute Place to Stay in San Jose
About Casai's Private Villas and Holiday Rentals in San Jose
Discover more than 867 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 364.97 ft², with nightly prices averaging US $129.
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 | 485 |
| Vacation Homes | 183 |
| 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
- Historic District Hidden Gem. The Best Location.
- Puerto del Buceo, habitación en Apartamento Compartido
- Cómodo apartamento vecino a feria de Tristán y a metros de 18 de julio
- Stylish Apartment with Balcony Cozy Stay in excellent Location
- Spacious illuminated and unique apartment
- Espacio Nodo I
- en el corazón del Barrio Sur
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.
- Casa Quinta en Montevideo, Melilla
- Edificio Lawa Calyptus
- Bungalow with garden, swimming pool, barbecue, pool, in an excellent location!
- Estancia Turística Don Joaquín
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:
- Charming house in Carrasco garden and beach
- en el corazón del Barrio Sur
- Hotel Montevideo - Leading Hotels of the World
How many Casai.nz holiday rentals are available in San Jose?
As of 2026, Casai boasts over 867 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.
People Also Ask
Finding the best prices in San Jose
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