Title: Bay Pines Vacation Packages 2026 from $504 | Expedia.com

[Bay Pines Travel Guide](https://expedia.com/St-Petersburg-Clearwater-Bay-Pines.dx6278551)[Hotels in Bay Pines](https://expedia.com/Bay-Pines-St-Petersburg-Clearwater-Hotels.0-n6278551-0.Travel-Guide-Filter-Hotels)[Flights to St. Petersburg - Clearwater](https://expedia.com/Cheap-Flights-To-St-Petersburg-Clearwater.d178310.Travel-Guide-Flights)[Things to do in St. Petersburg - Clearwater](https://expedia.com/Things-To-Do-In-St-Petersburg-Clearwater.d178310.Travel-Guide-Activities)[Car Rentals in Bay Pines](https://expedia.com/Car-Rentals-In-Bay-Pines.d6278551.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Bay Pines Vacations from $504

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

## 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](https://www.expedia.com/Johns-Pass-Village-Boardwalk-St-Petersburg-Clearwater.d6162658.Vacation-Attraction), [St. Petersburg - Clearwater Beaches](https://www.expedia.com/St-Petersburg-Clearwater-Beaches-Florida.d553248635976496951.Vacation-Attraction) and [Upham Beach](https://www.expedia.com/Upham-Beach-St-Petersburg-Clearwater.d6289260.Vacation-Attraction) 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.

![The Sarasota Modern, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/3763f29c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota

Save 100% on your flight

$504

per person

May 3 - May 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.2/10 Very Good! (530 reviews)

Staff were really friendly from front desk to bartenders to valet. Food was excellent and pool was nice with a fun vibe. Parts of hotel are dated and parts are newly renovated. It’s in a great location. I would return.

Reviewed on Mar 9, 2026

![voco Sarasota by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/6f2696b7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### voco Sarasota by IHG

Central Sarasota

$528

per person

May 20 - May 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

Great staff. Great airport shuttle.

Reviewed on Mar 10, 2026

![Arvilla](https://images.trvl-media.com/lodging/115000000/114820000/114812300/114812262/f3abbb67_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Arvilla

Sunshine Beach

Save 100% on your flight

$657

per person

May 16 - May 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

7.6/10 Good! (41 reviews)

Beautiful old school Florida motel. Recently renovated. Easy check in and out.

Reviewed on Mar 7, 2026

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/3006ffef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kompose Boutique Hotel

Save 100% on your flight

$622

per person

Jun 3 - Jun 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (5,088 reviews)

Good mattresses, clean rooms, friendly, helpful staff Needs laundry facilities

Reviewed on Mar 11, 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](https://expedia.com/St-Petersburg-Clearwater-Bay-Pines.dx6278551)

![Downtown St. Petersburg featuring outdoor art](https://images.trvl-media.com/place/6162954/a14552e2-b31c-40c8-9277-65c075c45565.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in Downtown St. Petersburg](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Downtown%20St.%20Petersburg&DestID=6162954&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Pass-a-Grille](https://images.trvl-media.com/place/6005248/23dce61e-1d6e-4228-8df5-1f3333e2a7fc.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Pass-a-Grille

5/5(26 area reviews)

 Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street. 

[Find hotel + flight trips in Pass-a-Grille](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Pass-a-Grille&DestID=6005248&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Beautiful morning rainbow over the gulf on Sand Key Beach located in Clearwater, FL. In the evening, the spectacular sunsets are a perfect way to end the day.](https://images.trvl-media.com/place/6033/b41a9954-2466-4f15-ad11-ddab1a91aa1b.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sand Key

1 out of top 10 points of interest in this area

4.5/5(108 area reviews)

 While visiting Sand Key, you might make a stop by sights like St. Petersburg - Clearwater Beaches and Belleair Beach. 

[Find hotel + flight trips in Sand Key](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Sand%20Key&DestID=553248635976482162&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Treasure Island which includes a beach and general coastal views](https://images.trvl-media.com/place/6159959/b4090095-e3ab-44c9-9d0d-a396aa62f0fb.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sunset Beach

4.5/5(37 area reviews)

 Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like St. Petersburg - Clearwater Beaches and Sunset Beach. 

[Find hotel + flight trips in Sunset Beach](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Sunset%20Beach&DestID=6159959&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Beautiful Sunset Moment #EK #MadeiraBeach](https://images.trvl-media.com/place/7329/748e44eb-7b5a-43f9-ad35-cef8c41bf71f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sunshine Beach

 If you're spending some time in Sunshine Beach, St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island are top sights worth seeing. 

[Find hotel + flight trips in Sunshine Beach](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Sunshine%20Beach&DestID=975330253044355072&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Bay Pines Hotel Deals

![Wyndham Grand Clearwater Beach](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/9591df75_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$404 nightly

$456 total

Apr 5 - Apr 6

Total with taxes and fees

9.4/10 Exceptional! (3,050 reviews)

Perfect view

Reviewed on Mar 9, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=15914352&PinnedHotelID=15914352&HadPinnedHotel=true&regionId=6278551)

![RumFish Beach at TradeWinds](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/923a3c65_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

RumFish Beach at TradeWinds

6000 Gulf Blvd St. Pete Beach FL

Fully refundableReserve now, pay when you stay

$360 nightly

$407 total

Mar 22 - Mar 23

Total with taxes and fees

8.4/10 Very Good! (1,670 reviews)

Very nice

Reviewed on Mar 11, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=8544&PinnedHotelID=8544&HadPinnedHotel=true&regionId=6278551)

![Hilton Clearwater Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/28100/28023/da46d3f6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$313 nightly

$354 total

Mar 24 - Mar 25

Total with taxes and fees

8.2/10 Very Good! (2,476 reviews)

Had to switch rooms right when I got there because the room was not cleaned, and there was blood on the door in the bathroom. The cleanliness of the property was low, pretty much all the rooms beed to be updated. The pool and ocean service and area were great though!

Reviewed on Mar 10, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=28023&PinnedHotelID=28023&HadPinnedHotel=true&regionId=6278551)

[See all 15,004 properties in Bay Pines](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&regionId=6278551)

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 Bay Pines

![Bay Pines VA Medical Center which includes signage](https://images.trvl-media.com/place/6277292/033c31cb-f912-471e-8668-17ee1589bfc6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/Bay-Pines-VA-Medical-Center-Bay-Pines.d6277292.Vacation-Attraction)

![Flag at half mast at the Veterans Memorial Island Sanctuary in Vero Beach, Florida.](https://images.trvl-media.com/place/6068755/72982f90-505a-4fbc-8f2c-fa0936d739ae.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### War Veteran Memorial Park

After visiting War Veteran Memorial Park, make a plan to see the other sights and activities in Madeira Beach. Amble around this family-friendly area's beautiful beaches or experience its great live music. 

[](https://expedia.com/War-Veteran-Memorial-Park-Bay-Pines.d6068755.Vacation-Attraction)

![Florida. Madeira Beach Florida. Gulf of Mexico or ocean beach, Hotels and Resorts. John's Pass Village and Boardwalk. Turquoise color of salt water. American shore. Summer or Autumn vacation.](https://images.trvl-media.com/place/6162658/626ce7e8-3da2-4f56-9ed1-b12b8c444765.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants. 

[](https://expedia.com/Johns-Pass-Village-Boardwalk-St-Petersburg-Clearwater.d6162658.Vacation-Attraction)

### Things to do

![Shell Key Island bird's eye view](https://mediaim.expedia.com/localexpert/179743/4e24a047-9028-4bbd-9bbf-c0b2a65e42d9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Shell Key Island Excursion

$64

per adult

**84%** of travellers recommend

[](https://expedia.com/things-to-do/shell-key-island-excursion.a179743.activity-details)

![Stunning view of dolphins in St. Petersburg, Florida  ](https://mediaim.expedia.com/localexpert/338288/367304c2-f6f9-4cca-9e9e-46b8251f0aad.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Dolphin Racer Speedboat Adventure

$36

per adult

**94%** of travellers recommend

[](https://expedia.com/things-to-do/dolphin-racer-speedboat-adventure.a338288.activity-details)

![View of the StarLite Sapphire Yacht on St. Pete Beach](https://mediaim.expedia.com/localexpert/614704/45a8896e-a19d-4260-bbc4-f0a060729fd7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### StarLite Sapphire Evening Yacht St. Pete Beach

$41

per adult

**90%** of travellers recommend

[](https://expedia.com/things-to-do/starlite-sapphire-evening-yacht-st-pete-beach.a614704.activity-details)

[See all activities in St. Petersburg - Clearwater](https://expedia.com/things-to-do/search?rid=6278551)

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