Leguisamo Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Leguisamo Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
Condado
$585
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to San Juan (SJU)
Book a stay at this luxury hotel in San Juan. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.
Room to smoll
Reviewed on Aug 14, 2026
Hotel Puerto Valdes
Puerta de Tierra
$721
per person
Sep 24 - Sep 28
found 19 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to San Juan (SJU)
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.
OLV Fifty Five - Adults Only
Condado
$848
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to San Juan (SJU)
Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Casino del Mar at La Concha Resort and Condado Beach are located nearby.
Aire de O:live
Isla Verde
$833
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to San Juan (SJU)
Book a stay at this luxury hotel in Carolina. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Isla Verde Beach and Jose Miguel Agrelot Coliseum are located nearby.
My stay here was amazing. Staff were phenomenal and property was very clean and beautiful. I’d stay here again.
Reviewed on Aug 14, 2026
Hyatt Regency Grand Reserve Puerto Rico
Zarzal
$894
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to San Juan (SJU)
Book a stay at this spa resort in Río Grande. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Luquillo Beach and Wyndham Rio Mar Casino are located nearby.
This place was truly a DREAM! From the moment we arrived, everything felt so beautiful, peaceful, and perfect. I honestly couldn’t believe how incredible everything was. The entire experience felt almost unreal.
This was, without a doubt, one of the most amazing vacations my family has ever had, and a huge part of that was staying here. The beauty, the atmosphere, the hospitality, and the overall experience exceeded every expectation I had.
I genuinely did NOT want to leave! If you’re considering staying here, let me save you the time—you absolutely should. I would recommend this place to ANYBODY and EVERYBODY looking for the perfect vacation experience.
Thank you for giving my family memories we’ll never forget. Until next time!
Reviewed on Aug 14, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
Old San Juan
$602
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to San Juan (SJU)
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.
Top Hotel Deals
Aquarius Vacation Club at Boqueron Beach Resort
Carretera 101 Km 18.1 Cabo Rojo
Book a stay at this beach hotel in Cabo Rojo. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
Rincon of the Seas - Grand Caribbean Hotel
Road 115 Km 12.2 Rincon
Book a stay at this beach hotel in Rincon. Enjoy free parking, a beach locale, and a rooftop terrace. Our guests praise the pool and the helpful staff in our ...
Holiday Inn Mayaguez and Tropical Casino by IHG
2701 Highway #2 Hostos Avenue Mayagüez
Book a stay at this business-friendly hotel in Mayagüez. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms ...
Villa Cofresi Hotel
Rd 115 Km 12.0 Rincon
Book a stay at this beach hotel in Rincon. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular ...
Lazy Parrot Inn
Carr. 413 Km 4.1, Bo. Puntas Rincon
Book a stay at this family-friendly resort in Rincon. Enjoy free WiFi, daily housekeeping, and a garden. Our guests praise the pool and the restaurant in our ...
Rincon Beach Resort
Road 115 KM 5.8 Añasco
Book a stay at this beach resort in Añasco. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
Punta Borinquen Resort
Belt Street, Ramey Base Aguadilla
Book a stay at this business-friendly resort in Aguadilla. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful ...
Parador El Faro
Carr. 107 Km 2.1 Aguadilla
Book a stay at this business-friendly hotel in Aguadilla. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hotel Mayaguez Plaza, BW Signature Collection
Calle Mendez Vigo 70 Este Mayagüez
Book a stay at this business-friendly hotel in Mayagüez. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our ...
Hotel Vista Azul
84 Ave Montemar Aguadilla Aguadilla
Book a stay at this business-friendly resort in Aguadilla. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Crash Boat Beach and Las Cascadas ...
Courtyard by Marriott Aguadilla
West Parade/Belt Road, Ramey Base Aguadilla
Book a stay at this golf hotel in Aguadilla. Enjoy free WiFi, 2 outdoor pools, and a casino. Our guests praise the helpful staff in our reviews. Popular attractions ...
Parguera Plaza Hotel - Adults Only
Street 304 Km 3.2 Lajas
Book a stay at this beach hotel in Lajas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Bella Surf Inn
Carr. 4466 Km 0.1 Isabela
Book a stay at this beach hotel in Isabela. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Hotel Vista Verde
Puerto Rico 368 Yauco Yauco
Book a stay at this business-friendly hotel in Yauco. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Río Loco Lake and Lucchetti Lake ...
Tryp by Wyndham Mayaguez
11 CALLE SANTIAGO RIERA PALMER Mayagüez
Stay at this hotel in Mayagüez. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Sep 15 - Thu, Sep 17
FLL
Fort Lauderdale - Hollywood Intl.
SJU
Luis Munoz Marin Intl.
$110
Roundtrip
found 6 days ago
Wed, Sep 16 - Thu, Sep 17
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$232
Roundtrip
found 2 days ago
Sat, Sep 12 - Sat, Sep 19
LGA
LaGuardia
SJU
Luis Munoz Marin Intl.
$246
Roundtrip
found 3 days ago
Tue, Oct 13 - Fri, Oct 16
FLL
Fort Lauderdale - Hollywood Intl.
BQN
Rafael Hernandez
$277
Roundtrip
found 3 days ago
Mon, Feb 15 - Sat, Feb 20
EWR
Newark Liberty Intl. Airport
BQN
Rafael Hernandez
$627
Roundtrip
found 5 days ago
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