Vacation Rentals with Private Pool in Obrero, San Juan: Compare 10+ Sites & Save

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171 Best Vacation Rentals with Private Pool in Obrero (Starting from $181)

Satisfaction
Satisfaction
Apartment
San Juan, Puerto Rico
1.9k from Obrero center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom6 Guests
7.6

Good

120 reviews

$225
Average price / night
Check Availability
Driver, Chef, Maid, & Pool - VIP Service
Driver, Chef, Maid, & Pool - VIP Service
Apartment
San Juan, 00913, Puerto Rico
1.7k from Obrero center

AC, Breakfast Included, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms18 Guests
New to Booking
$1499
Average price / night
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Couples Suites at Ocean Park Beach Club
Couples Suites at Ocean Park Beach Club
House
San Juan, Puerto Rico
2.0k from Obrero center

B&bs, Cheap, Accommodations, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay, Family

8 Bedrooms24 Guests
9.5

Superb

6 reviews

$249
Average price / night
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Private Pool Piscina Privada by CasaSaffra
Private Pool Piscina Privada by CasaSaffra
Apartment
San Juan, 00913, Puerto Rico
1.7k from Obrero center

AC, Barbecue, Crib, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

4 Bedrooms10 Guests
6.0

Review score

1 reviews

$708
Average price / night
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Cacique Vacation Rental by Otium
Cacique Vacation Rental by Otium
Apartment
San Juan, Puerto Rico
2.0k from Obrero center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

4 Bedrooms10 Guests
New to Booking
$181
Average price / night
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5 Bedroom with Private Pool NEXT TO BEACH
5 Bedroom with Private Pool NEXT TO BEACH
House
San Juan, 00913, Puerto Rico
1.7k from Obrero center

AC, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio

5 Bedrooms12 Guests
2.0

Review score

1 reviews

$856
Average price / night
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Apartamento con vistas al mar Isla Verde Puerto Rico
Apartamento con vistas al mar Isla Verde Puerto Rico
Apartment
San Juan, Puerto Rico
2.6k from Obrero center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Beach, Places to stay

5 Bedrooms20 Guests
New to Booking
$405
Average price / night
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This listing is for two (2) spacious  homes, next to each other
This listing is for two (2) spacious homes, next to each other
House
San Juan, 00913, Puerto Rico
1.7k from Obrero center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

9 Bedrooms23 Guests
New to Booking
$1547
Average price / night
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Atlantic View
Atlantic View
Apartment
San Juan, Puerto Rico
3.0k from Obrero center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Accessible hotels, Beach rentals

2 Bedrooms6 Guests
8.3

Very Good

3 reviews

$284
Average price / night
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Location is Everything  3and a Half  Bedroom
Location is Everything 3and a Half Bedroom
Apartment
San Juan, 00912, Puerto Rico
1.7k from Obrero center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$491
Average price / night
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Lullaby of the Sea
Lullaby of the Sea
Apartment
San Juan, Puerto Rico
3.0k from Obrero center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Accessible hotels, Beach rentals

1 Bedroom8 Guests
8.5

Very Good

4 reviews

$378
Average price / night
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Tropical San Juan Life with Pool
Tropical San Juan Life with Pool
Apartment
San Juan, 00912, Puerto Rico
1.7k from Obrero center

AC, Barbecue, Crib, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms9 Guests
New to Booking
$508
Average price / night
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Lady from Spain
Lady from Spain
Apartment
San Juan, Puerto Rico
3.1k from Obrero center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Accessible hotels

3 Bedrooms7 Guests
9.0

Fabulous

2 reviews

$458
Average price / night
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Tropical Modern Getaway in Central Location
Tropical Modern Getaway in Central Location
Apartment
San Juan Condado, 00912, Puerto Rico
1.7k from Obrero center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
New to Booking
$493
Average price / night
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Apartamentos en excelente Zona Condado, San Juan, Puerto Rico
Apartamentos en excelente Zona Condado, San Juan, Puerto Rico
Apartment
San Juan, Puerto Rico
3.1k from Obrero center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Places to stay

5 Bedrooms2 Guests
New to Booking
$407
Average price / night
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\"Tropical Villa Isabel\" - your Puerto Rico paradise!
\"Tropical Villa Isabel\" - your Puerto Rico paradise!
House
San Juan, 00913, Puerto Rico
1.8k from Obrero center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$836
Average price / night
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El Capitan
El Capitan
Apartment
San Juan, Puerto Rico
3.1k from Obrero center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Accessible hotels, Beach rentals

1 Bedroom4 Guests
8.6

Fabulous

7 reviews

$275
Average price / night
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Riviera Villa 8Bd 5ba Pool/Hot Tub @Ocean Park
Riviera Villa 8Bd 5ba Pool/Hot Tub @Ocean Park
House
San Juan, 00911, Puerto Rico
1.8k from Obrero center

AC, Balcony, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

8 Bedrooms16 Guests
New to Booking
$1740
Average price / night
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Isla Bella
Isla Bella
Apartment
San Juan, Puerto Rico
3.1k from Obrero center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Accessible hotels, Beach rentals

2 Bedrooms6 Guests
8.7

Fabulous

9 reviews

$264
Average price / night
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Casa Palmera Ocean Park – 7BR, Pool, Outdoor Space & Beach Nearby.
Casa Palmera Ocean Park – 7BR, Pool, Outdoor Space & Beach Nearby.
House
San Juan, 00913, Puerto Rico
1.8k from Obrero center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

7 Bedrooms16 Guests
New to Booking
$1209
Average price / night
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Moderno Apartamento para parejas San Juan Puerto Rico
Moderno Apartamento para parejas San Juan Puerto Rico
Apartment
San Juan, Puerto Rico
3.1k from Obrero center

Internet, Security/Safety, Private Pool, Transportation/Shuttle, Parking, Guest Services, Pet Friendly

1 Bedroom2 Guests
New to Booking
$472
Average price / night
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Luxurious And Beautiful  Beach House With Pool In Ocean Park  (SEE VIDEO)
Luxurious And Beautiful Beach House With Pool In Ocean Park (SEE VIDEO)
House
San Juan, 00913, Puerto Rico
1.8k from Obrero center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

6 Bedrooms14 Guests
9.2

Superb

141 reviews

$896
Average price / night
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Three units, One property
Three units, One property
Villa
San Juan, 00913, Puerto Rico
1.8k from Obrero center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

15 reviews

$1068
Average price / night
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Santorini Villa OceanParkPool BeachHouse
Santorini Villa OceanParkPool BeachHouse
House
San Juan, 00911, Puerto Rico
1.9k from Obrero center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Internet, Kitchen

9 Bedrooms23 Guests
9.2

Superb

7 reviews

$1938
Average price / night
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General Patton
General Patton
House
San Juan, 00913, Puerto Rico
1.9k from Obrero center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

7 Bedrooms16 Guests
9.0

Fabulous

6 reviews

$1241
Average price / night
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Ocean Park Beach Club Full
Ocean Park Beach Club Full
Apartment
San Juan, 00913, Puerto Rico
1.9k from Obrero center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

14 Bedrooms30 Guests
10.0

Exceptional

1 reviews

$6969
Average price / night
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Portocafe Ocean Park Home 5Bd/4b Pool WalkToBeach
Portocafe Ocean Park Home 5Bd/4b Pool WalkToBeach
House
San Juan, 00911, Puerto Rico
1.9k from Obrero center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1024
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Obrero.

Stay Near Obrero's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Obrero Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 171 verified vacation rentals with a private pool in Obrero. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Obrero vary depending on the property size, location, and travel season. Rates typically start from around $181 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Obrero also welcome pets. Currently, 16 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Obrero often include additional features such as Private Pool, Pool, and Internet. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Obrero include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.