Vacations Close To Pineapple Island

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Pineapple Island Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Tampa North by IHG

Holiday Inn Tampa North by IHG

3 out of 5
Terrace Park
Price was $837, price is now $721 per person
$721
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)
Great staff, comfortable room, great amenities. Responsive to our needs

Reviewed on Nov 5, 2026

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,352, price is now $949 per person
$949
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)
N/A I won't book again. I have been to better resorts. For the money they charge I had torn curtains in my room and sugar ants and s stopped up tub that I had to call the maintenance

Reviewed on Nov 3, 2026

Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
Rocky Point
Price was $1,227, price is now $902 per person
$902
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
Price was $1,205, price is now $909 per person
$909
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)

The Westshore Grand, Tampa, A Tribute Portfolio Hotel

The Westshore Grand, Tampa, A Tribute Portfolio Hotel

4 out of 5
Beach Park
Price was $1,405, price is now $1,082 per person
$1,082
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)

Holiday Inn Express & Suites Ruskin by IHG

Holiday Inn Express & Suites Ruskin by IHG

2.5 out of 5
Price was $1,058, price is now $858 per person
$858
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

2.5 out of 5
Price was $1,183, price is now $983 per person
$983
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)

ROOST Tampa

ROOST Tampa

4 out of 5
Downtown Tampa
Price was $1,374, price is now $1,142 per person
$1,142
per person
Dec 24 - Jan 1
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Tampa (TPA)

Don't see what you're looking for?
See all available trips from Columbus to Pineapple Island
View all trips

Best Lodging Options Near Pineapple Island

Hotel Sol

Hotel Sol

2.5 out of 5
17566 Gulf Blvd Redington Shores FL
1.62 km from Pineapple Island
Book a stay at this beach hotel in Redington Shores. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

DoubleTree Beach Resort by Hilton Tampa Bay - North Redingto

4 out of 5
17120 Gulf Blvd North Redington Beach FL
1.57 km from Pineapple Island
Book a stay at this beach hotel in North Redington Beach. Enjoy a beach locale, 2 bars/lounges, and room service. Our guests praise the helpful staff and the ...
Malibu Resort Motel

Malibu Resort Motel

2 out of 5
17001 Gulf Blvd. North Redington Beach FL
1.49 km from Pineapple Island
Stay at this motel in North Redington Beach. Enjoy free parking, daily housekeeping, and a garden. Our guests praise the helpful staff and the clean rooms in ...
Island House Hotel

Island House Hotel

2 out of 5
17103 Gulf Boulevard North Redington Beach FL
1.51 km from Pineapple Island
Stay at this hotel in North Redington Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Sand Vista Vacation Rentals

Sand Vista Vacation Rentals

2 out of 5
17495 Gulf Blvd Redington Shores FL
1.51 km from Pineapple Island
Stay at this motel in Redington Shores. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Carousel Suites

Carousel Suites

2.5 out of 5
18202 Gulf Blvd Redington Shores FL
2.1 km from Pineapple Island
Book a stay at this beach motel in Redington Shores. Enjoy free WiFi, free parking, and a beach shuttle (surcharge). Our guests praise the helpful staff in our ...
Don't see what you're looking for?
See all available properties in Pineapple Island
View all properties
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.