Bay Pines Vacations from $437

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Your Bay Pines Vacation

Unforgettable adventures await when you book a Bay Pines vacation package. Whether you're a foodie, history enthusiast or just a traveler who appreciates new places, there's something for everyone in this awesome city. Johns Pass Village & Boardwalk, St. Petersburg - Clearwater Beaches and Upham Beach are just some of the many attractions worth exploring during your trip to Bay Pines. Expedia will help you escape your daily routine. Tailor your vacation to Bay Pines to suit your travel style, whatever that may look like.

The Latest Bay Pines Vacation Packages

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

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,070, price is now $437 per person
$437
per person
Mar 1 - Mar 6
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended

Reviewed on Jan 1, 2026

Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Save 100% on your flight
Price was $1,018, price is now $499 per person
$499
per person
Mar 14 - Mar 19
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
2/10 (2 reviews)
Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Save 100% on your flight
Price was $1,018, price is now $527 per person
$527
per person
Feb 6 - Feb 10
just found
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
7.6/10 Good! (4 reviews)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,764, price is now $1,114 per person
$1,114
per person
Mar 12 - Mar 15
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Beautiful updated room, bathroom was perfect with soaps, lotions, shampoos. The front desk service was very friendly and helpful. Problems: empty water bottles in the room were dirty Bar out of any red wine, restaurant out of coffee creamer. Would stay here again

Reviewed on Jan 4, 2026

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $1,396, price is now $917 per person
$917
per person
Feb 6 - Feb 13
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Tampa (TPA)
8.8/10 Excellent! (417 reviews)
Hidden gem. Great for kids. Warm pool even in December. Fire pits. Jenga. Beach. Dolphin views on Tampa bay. Comfy pool and beach furniture. Nice restaurant. And great places to hang all over the property. Only downside , beds were small.

Reviewed on Jan 2, 2026

Where to stay in Bay Pines

Find the best Bay Pines areas and neighborhoods for the activities you enjoy most. Learn more about Bay Pines
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

Bay Pines Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$325 nightly
The price is $367 total per night from Jan 7 to Jan 8
$367 total
Jan 7 - Jan 8
Total with taxes and fees
9.4/10 Exceptional! (2,972 reviews)
Amazing hotel - great location, close to lots of restaurants and bars, and it's right across the street from the beach. We had the intercoastal view room and enjoyed views of beautiful sunrises every morning. The breakfast buffet was delicious, lots of variety and great service - so glad we booked ...

Reviewed on Jan 3, 2026

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $236 total per night from Jan 11 to Jan 12
$236 total
Jan 11 - Jan 12
Total with taxes and fees
8/10 Very Good! (2,392 reviews)
Very courteous staff, great location

Reviewed on Jan 4, 2026

Hilton Clearwater Beach Resort & Spa
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Jan 7 to Jan 8
$98 total
Jan 7 - Jan 8
Total with taxes and fees
6.2/10 (3,739 reviews)
Clean

Reviewed on Dec 30, 2025

Ramada by Wyndham Tampa Westshore Airport South
See all 14,875 properties in Bay Pines
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Bay Pines

Bay Pines VA Medical Center which includes signage

Bay Pines VA Medical Center

Though Bay Pines VA Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Madeira Beach while you are here.

Bay Pines VA Medical Center
John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches

Things to do

Dolphin Watching Nature Cruise and Eco Tour from Hubbard's Marina in John's Pass

Dolphin Watching Nature Cruise and Eco Tour from Hubbard's Marina in John's Pass

$29
per adult
100% of travellers recommend
Dolphin Watching Nature Cruise and Eco Tour from Hubbard's Marina in John's Pass
Madeira Beach: Pirate Adventure Cruise

Madeira Beach: Pirate Adventure Cruise

$45
per adult
100% of travellers recommend
Madeira Beach: Pirate Adventure Cruise
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

$67
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.