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San Mateo Vacation Packages

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San Mateo Flight + Hotel Packages

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

Casa Drake

3 out of 5
Price was $1,045, price is now $564 per person
$564
per person
May 13 - May 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Stay at this lodge in Drake Bay. Enjoy free breakfast, a lazy river, and an airport shuttle (surcharge). Popular attractions San Josecito Beach and Playa Rincon are located nearby.
The Springs Resort and Spa at Arenal

The Springs Resort and Spa at Arenal

5 out of 5
Price was $3,145, price is now $1,649 per person
$1,649
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
Book a stay at this luxury resort in Monterrey. Enjoy free WiFi, free parking, and 15 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Arenal Volcano National Park and Los Lagos Hot Springs are located nearby.
Namu Garden Hotel & Spa - Adults Only

Namu Garden Hotel & Spa - Adults Only

4.5 out of 5
Save 100% on your flight
Price was $1,995, price is now $1,101 per person
$1,101
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
Book a stay at this luxury hotel in Cahuita. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Punta Uva Beach and Talamanca Family Art are located nearby.
Si Como No Resort, Spa and Wildlife Refuge

Si Como No Resort, Spa and Wildlife Refuge

3.5 out of 5
Save 100% on your flight
Price was $1,864, price is now $1,054 per person
$1,054
per person
May 21 - May 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Book a stay at this spa resort in Quepos. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Manuel Antonio Nature Park & Wildlife Refuge and Manuel Antonio Beach are located nearby.
Vista Suites at Parador

Vista Suites at Parador

2.5 out of 5
Save 100% on your flight
Price was $4,326, price is now $2,468 per person
$2,468
per person
Jun 22 - Jun 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San José (SJO)
Book a stay at this spa hotel in Quepos. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Manuel Antonio Nature Park & Wildlife Refuge and Manuel Antonio Beach are located nearby.
Senda Monteverde Hotel Member of the Cayuga Collection

Senda Monteverde Hotel Member of the Cayuga Collection

4 out of 5
Save 100% on your flight
Price was $2,815, price is now $1,639 per person
$1,639
per person
Jul 1 - Jul 8
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Stay at this hotel in Monteverde. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Monteverde Cloud Forest Biological Reserve and Jardín de Orquídeas are located nearby.
Ocean View Penthouses by Issimo - Adults Only

Ocean View Penthouses by Issimo - Adults Only

3.5 out of 5
Save 100% on your flight
Price was $1,665, price is now $980 per person
$980
per person
May 20 - May 24
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Book a stay at this beach hotel in Quepos. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Manuel Antonio Nature Park & Wildlife Refuge and Manuel Antonio Beach are located nearby.
Monte Carlo Luxury Condominiums

Monte Carlo Luxury Condominiums

3.5 out of 5
Price was $1,518, price is now $898 per person
$898
per person
May 21 - May 26
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
Stay at this aparthotel in Jacó. Enjoy free WiFi, free parking, and room service. Our guests praise the property condition in our reviews. Popular attractions Jacó Beach and Marina Los Sueños are located nearby.

San Mateo Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Si Como No Resort, Spa and Wildlife Refuge

Si Como No Resort, Spa and Wildlife Refuge

3.5 out of 5
Manuel Antonio
Save 100% on your flight
Price was $1,648, price is now $892 per person
$892
per person
Jun 18 - Jun 22
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Ocean View Penthouses by Issimo - Adults Only

Ocean View Penthouses by Issimo - Adults Only

3.5 out of 5
Manuel Antonio
Save 100% on your flight
Price was $1,665, price is now $980 per person
$980
per person
May 20 - May 24
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Vista Suites at Parador

Vista Suites at Parador

2.5 out of 5
Manuel Antonio
Save 100% on your flight
Price was $2,453, price is now $1,466 per person
$1,466
per person
May 20 - May 24
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
Arenas Del Mar Beachfront & Rainforest Member of the Cayuga Collection

Arenas Del Mar Beachfront & Rainforest Member of the Cayuga Collection

4.5 out of 5
Manuel Antonio
Save 100% on your flight
Price was $3,320, price is now $2,014 per person
$2,014
per person
May 20 - May 24
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)

San Mateo Vacation Packages 5-7 Night Stays

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

Casa Drake

3 out of 5
Price was $1,045, price is now $564 per person
$564
per person
May 13 - May 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)
The Springs Resort and Spa at Arenal

The Springs Resort and Spa at Arenal

5 out of 5
Price was $3,145, price is now $1,649 per person
$1,649
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
Namu Garden Hotel & Spa - Adults Only

Namu Garden Hotel & Spa - Adults Only

4.5 out of 5
Save 100% on your flight
Price was $1,995, price is now $1,101 per person
$1,101
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
Ocean View Penthouses by Issimo - Adults Only

Ocean View Penthouses by Issimo - Adults Only

3.5 out of 5
Manuel Antonio
Price was $2,151, price is now $1,204 per person
$1,204
per person
May 26 - May 31
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to San José (SJO)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Thu, May 28 - Fri, May 29
MIA
Miami Intl.
SJO
Juan Santamaría Intl.
$290 Roundtrip, found 1 hour ago
$290
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, May 28 from Miami Intl. to Juan Santamaría Intl., returning Fri, May 29, priced at $290 found 1 hour ago
Spirit Airlines
Thu, May 14 - Fri, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
SJO
Juan Santamaría Intl.
$307 Roundtrip, found 19 hours ago
$307
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Juan Santamaría Intl., returning Fri, May 29, priced at $307 found 19 hours ago
American Airlines
Mon, Apr 27 - Tue, May 12
BOS
Logan Intl.
SJO
Juan Santamaría Intl.
$312 Roundtrip, found 8 hours ago
$312
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Logan Intl. to Juan Santamaría Intl., returning Tue, May 12, priced at $312 found 8 hours ago
Spirit Airlines
Wed, May 6 - Fri, May 8
LGA
LaGuardia
SJO
Juan Santamaría Intl.
$319 Roundtrip, found 8 hours ago
$319
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Wed, May 6 from LaGuardia to Juan Santamaría Intl., returning Fri, May 8, priced at $319 found 8 hours ago