Crossroads Area Vacations from $603

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Your Crossroads Area Vacation

Your next escape is calling your name with a vacation package to Crossroads Area. Fun, food and great times — you're bound to find it in this neighborhood. Hoping to sightsee during your trip to Crossroads Area? Make sure you stop by nearby attractions such as Johns Pass Village & Boardwalk, St. Petersburg Municipal Beach and Hubbards Marina. Expedia will help put your travel plans into action. Book your perfect Crossroads Area vacation today.

The Latest Crossroads Area Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,027, price is now $603 per person
$603
per person
Nov 8 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
Clean, nice staff just could add more activity’s

Reviewed on Oct 1, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,136, price is now $623 per person
$623
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
A nice hotel with a European flare. Very close to the center of town with lots of restaurants.

Reviewed on Oct 1, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,229, price is now $763 per person
$763
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Everything was awesome!

Reviewed on Sep 28, 2025

St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
Price was $2,960, price is now $1,847 per person
$1,847
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (967 reviews)
Staff here is always very nice and attentive. Location is GREAT! Very short 2min walk to beach on a quiet street. The beach has $45 chairs with umbrella rentals if you need it. Paradise Grill is on the beach with beach fare and bar drinks. Delicious! Night life is a couple blocks away with live bands/ DJ. Corey Street is fun too. They have a Sunday farmers/craft market and some cute shops. Lots of yummy restaurants near by. We had dinner at Snappers. Great Seafood. We had a king bedroom. Bed and pillows were comfortable. Ac worked well and it had ceiling fans too. The pool was clean and a great temp. There are also ice-cream shops walking distance too. WE love Upham Beach.

Reviewed on Sep 29, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,245, price is now $778 per person
$778
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,007 reviews)
The hotel was under some type of construction. The pool was closed, it would've been nice to know this before booking.

Reviewed on Sep 27, 2025

Where to stay in Crossroads Area

Find the best Crossroads Area areas and neighborhoods for the activities you enjoy most. Learn more about Crossroads Area
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

Crossroads Area Hotel Deals

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
$213 nightly
The price is $240 total per night from Oct 9 to Oct 10
$240 total
Oct 9 - Oct 10
Total with taxes and fees
8/10 Very Good! (2,232 reviews)
"All"

Reviewed on Sep 29, 2025

Hilton Clearwater Beach Resort & Spa
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
333 1st St S, St. Petersburg, FL
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $132 total per night from Oct 5 to Oct 6
$132 total
Oct 5 - Oct 6
Total with taxes and fees
7.6/10 Good! (1,027 reviews)
"The vallet parking is pricy at $45 a day. The hotel doesn’t have any self parking area or options."

Reviewed on Sep 27, 2025

Hilton St. Petersburg Bayfront
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
$287 nightly
The price is $324 total per night from Oct 24 to Oct 25
$324 total
Oct 24 - Oct 25
Total with taxes and fees
9.2/10 Wonderful! (2,697 reviews)
"The view was awesome, the staff was very professional and helpful. Thank you for a great stay!"

Reviewed on Oct 1, 2025

Wyndham Grand Clearwater Beach
See all 16,082 properties in Crossroads Area
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 Crossroads Area

John's Pass Village & Boardwalk

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 marina in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
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

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$32
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.