Title: San Mateo Vacation Packages 2026 from $633 | Expedia.com

[Hotels in San Mateo](https://expedia.com/San-Mateo-Hotels.d553248635976395377.Travel-Guide-Hotels)[Car Rentals in San Mateo](https://expedia.com/Car-Rentals-In-San-Mateo.d553248635976395377.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# San Mateo Vacations from $633

## Book a Hotel + Flight or Car together to unlock savings

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## Your San Mateo Vacation

Book a San Mateo vacation package and discover the rhythm and vibe of this interesting neighborhood. With all your travel plans taken care of, the only thing you need to concentrate on here is living your best life. Wondering what to see and do during your trip to San Mateo? Nearby attractions like [Jose Miguel Agrelot Coliseum](https://www.expedia.com/Jose-Miguel-Agrelot-Coliseum-Hato-Rey-Norte.d6116702.Vacation-Attraction), [Hiram Bithorn Stadium](https://www.expedia.com/Hiram-Bithorn-Stadium-Hato-Rey-Norte.d502601.Vacation-Attraction) and [Condado Beach](https://www.expedia.com/Condado-Beach-Santurce.d6082351.Vacation-Attraction) are great places to start. Don't just think about it — turn it into reality! Secure your ultimate San Mateo vacation with Expedia and get to where you're going your way.

## The Latest San Mateo Vacation Packages

Price found within the past 48 hours. Click for updated prices.

![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Puerto Valdes

San Juan Antiguo

Save 100% on your flight

$633

per person

Jun 6 - Jun 10

found 2 days ago

Roundtrip non-stop flight included

Boston (BOS) to San Juan (SJU)

8.8/10 Excellent! (594 reviews)

The room was comfortable overall, but I was concerned that the door bolt was not functioning properly. Additionally, one of the blinds was broken and couldn’t be raised, which limited natural light in the room.

Reviewed on Mar 28, 2026

![Lazy Parrot Inn](https://images.trvl-media.com/lodging/1000000/910000/900400/900306/d84e57b2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lazy Parrot Inn

Save 100% on your flight

$681

per person

Jun 14 - Jun 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.2/10 Wonderful! (1,007 reviews)

Loved this room. Clean and comfortable- quiet yet accessible. Highly recommend.

Reviewed on Mar 23, 2026

![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Aire de O:live

Isla Verde

Save 100% on your flight

$725

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.2/10 Wonderful! (469 reviews)

Great beach place. Walk right out to beach. Waited service on beach. Staff opens the door for you. Foods good. What else do you need?…

Reviewed on Mar 22, 2026

![Serenity by Otium](https://images.trvl-media.com/lodging/126000000/125160000/125154600/125154508/8257213d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Serenity by Otium

Save 100% on your flight

$1,319

per person

Jun 14 - Jun 20

found 11 hours ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

No reviews

![Hyatt Vacation Club at Hacienda del Mar, Dorado](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/b302112a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Hacienda del Mar, Dorado

Sabana

$969

per person

May 2 - May 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to San Juan (SJU)

9.4/10 Exceptional! (3,304 reviews)

This is my second time staying here and loved it both times! Rooms are beautiful with gorgeous views. Staff is really friendly. The restaurant on site called Mahi Mahi is really good and reasonably priced.

Reviewed on Mar 25, 2026

## Where to stay in San Mateo

Find the best San Mateo areas and neighborhoods for the activities you enjoy most. [Learn more about San Mateo](https://expedia.com/San-Juan-San-Mateo.dx553248635976395377)

![Old San Juan](https://images.trvl-media.com/place/553248633981709498/285d265c-4268-4cc4-9dc2-9fb6e2e1f6af.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Old San Juan

4.5/5(360 area reviews)

 The fascinating museums and captivating waterfront views are top of the list for many visitors to Old San Juan. A stop by Port of San Juan or Castillo de San Cristobal might round out your trip. 

[Find hotel + flight trips in Old San Juan](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Old%20San%20Juan&DestID=553248633981709498&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Isla Verde](https://images.trvl-media.com/place/6139938/233b223a-97e9-4ba1-901f-12d14e70222e.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Isla Verde

4/5(692 area reviews)

 White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico. 

[Find hotel + flight trips in Isla Verde](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Isla%20Verde&DestID=6139938&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Condado](https://images.trvl-media.com/place/506189/30f3a227-250d-400a-ad63-ee532120010a.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Condado

1 out of top 10 points of interest in this area

4.5/5(766 area reviews)

 Oceanfront and upscale, Condado boasts picturesque beaches alongside hotels, nightclubs, casinos, and shops. Stroll through La Ventana al Mar park, and enjoy easy access to public transport via T21 and D53 bus routes. 

[Find hotel + flight trips in Condado](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Condado&DestID=506189&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Santurce](https://images.trvl-media.com/place/6081953/483f59d0-b2e5-4953-9ef8-21e7542b5728.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Santurce

2 out of top 10 points of interest in this area

 Bask in the sun on Atlantic Ocean beaches and experience vibrant nightlife at La Placita de Santurce, while exploring museums like the Museum of Art of Puerto Rico. Enjoy easy access to public transportation via bus lines and the Tren Urbano. 

[Find hotel + flight trips in Santurce](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Santurce&DestID=553248635975438457&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Ocean Park](https://images.trvl-media.com/place/6082360/eff1cd71-2d6e-4ed2-9547-8ff8099874ae.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Ocean Park

4.5/5(277 area reviews)

 Upscale beachfront community with trendy beachgoers, Ocean Park offers kitesurfing and windsurfing opportunities. Stroll along Calle Loíza for bars, restaurants, and boutiques or unwind at nearby Parque Barbosa. 

[Find hotel + flight trips in Ocean Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Ocean%20Park&DestID=6082360&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## San Mateo Hotel Deals

![The Looking Glass Hotel](https://images.trvl-media.com/lodging/100000000/99050000/99049700/99049607/98e5bf0c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Looking Glass Hotel

1661 Av. Juan Ponce de León San Juan Puerto Rico

Fully refundableReserve now, pay when you stay

$114 nightly

$125 total

Apr 20 - Apr 21

Total with taxes and fees

9.4/10 Exceptional! (351 reviews)

The photos online were deceiving. The bed sheets had long hair and stains what makes me believe that they were not changing. The shower was another deal the sink was inside the shower, so it got all wet. The toilet had is on story was off center so while seating you hit your lees on the wall. The ...

Reviewed on Mar 27, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F20%2F2026&endDate=4%2F21%2F2026&selected=99049607&PinnedHotelID=99049607&HadPinnedHotel=true&regionId=553248635976395377)

![Hyatt Vacation Club at Hacienda del Mar, Dorado](https://images.trvl-media.com/lodging/1000000/910000/902000/901912/b302112a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Vacation Club at Hacienda del Mar, Dorado

301 Hwy 693 Vega Alta 

$311 nightly

$339 total

Apr 19 - Apr 20

Total with taxes and fees

9.4/10 Exceptional! (3,352 reviews)

I loved it. It was a perfect getaway. I had everything you needed in the resort without having to venture off. It was a little far from the airport, but the area that the resort was in was beautiful kind of like the suburbs I would say, and there were stores within five minute drive from the hotel ...

Reviewed on Mar 27, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=901912&PinnedHotelID=901912&HadPinnedHotel=true&regionId=553248635976395377)

![Caribe Hilton](https://images.trvl-media.com/lodging/1000000/10000/9300/9228/ae0d235f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Caribe Hilton

1 San Geronimo Street San Juan 

Fully refundableReserve now, pay when you stay

$354 nightly

$386 total

Apr 28 - Apr 29

Total with taxes and fees

8.6/10 Excellent! (2,617 reviews)

Everything was great except the person at the front desk when we checked in went on and on how many Hilton Honors points we would receive from our stay, and encouraged us to charge everything on the property to the room so we would receive 2X points. So we spent over $1,300 on the property in four ...

Reviewed on Mar 25, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F28%2F2026&endDate=4%2F29%2F2026&selected=9228&PinnedHotelID=9228&HadPinnedHotel=true&regionId=553248635976395377)

[See all 3,858 properties in San Mateo](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&regionId=553248635976395377)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Discover the most popular places to visit in San Mateo

![San Juan Cruise Port, Puerto Rico](https://images.trvl-media.com/place/6227475/39a3ae76-4944-4651-9195-2a2fd4be46bc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Port of San Juan

Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene. 

[](https://expedia.com/Port-Of-San-Juan-San-Juan-Antiguo.d6227475.Vacation-Attraction)

![Condado Beach](https://images.trvl-media.com/place/6082351/117e9763-237d-44f2-8449-eb8094c439f1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Condado Beach

This beach within the bustling city of San Juan is the perfect place to relax for a few hours.

[](https://expedia.com/Condado-Beach-Santurce.d6082351.Vacation-Attraction)

![Luquillo Beach](https://images.trvl-media.com/place/6081853/29e71293-11d7-4d82-8a80-15b2697e5634.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Luquillo Beach

Sample local street food or doze under a palm tree on this picturesque stretch of coast.

[](https://expedia.com/Luquillo-Beach-San-Juan.d6081853.Vacation-Attraction)

### Things to do

![Best of Old San Juan Walking Tour with El Morro Entry](https://mediaim.expedia.com/localexpert/50581240/664c5cd7-486f-476d-8261-d5b35d926be9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Best of Old San Juan Walking Tour with El Morro Entry

$49

per adult

**100%** of travellers recommend

[](https://expedia.com/things-to-do/best-of-old-san-juan-walking-tour-with-el-morro-entry.a50581240.activity-details)

![El Yunque Rainforest Guided Hiking with Waterfall Tour](https://mediaim.expedia.com/localexpert/478689/4c1c01b7-c003-4100-ae20-901ec3f5ff50.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### El Yunque Rainforest Guided Hiking Tour

$88

per traveler

**96%** of travellers recommend

[](https://expedia.com/things-to-do/el-yunque-rainforest-guided-hiking-tour.a478689.activity-details)

![FlyDining: Sunset & City Lights Dinner Over Old San Juan](https://mediaim.expedia.com/localexpert/47551559/3f319115-d1e4-46fe-ac4f-34f62c27ab5f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### FlyDining: 4 Course Sunset & City Light Dinner Over Old San Juan

$159

per adult

**92%** of travellers recommend

[](https://expedia.com/things-to-do/flydining-4-course-sunset-city-light-dinner-over-old-san-juan.a47551559.activity-details)

[See all activities in San Juan](https://expedia.com/things-to-do/search?rid=553248635976395377)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.