Name: Wyndham Grand Clearwater Beach
Price range: $448 total
Rating: 9.4

Your Island Estate Vacation

Discover the unique character of Island Estate with a tailor-made Island Estate vacation package. From its watersports to its nature, this neighborhood offers endless possibilities for relaxation and adventure. Can't wait to get out and see the sights during your trip to Island Estate? Don't miss nearby attractions such as Clearwater Marine Aquarium, Sand Key Park and Pier 60 Park. No matter your travel goals or the size of your budget, booking the ultimate Island Estate vacation is easy with Expedia.

The Latest Island Estate Vacation Packages

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

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$617

per person

May 15 - May 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (2,261 reviews)

Very clean and comfortable. Everything needed for a great stay!

Reviewed on Mar 6, 2026

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$640

per person

May 15 - May 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

Very friendly staff and clean rooms

Reviewed on Mar 9, 2026

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

The Fold Hotels Indian Shores

Save 100% on your flight

$986

per person

May 22 - May 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (952 reviews)

Spotless room, comfortable beds, very accommodating staff. Will definitely star again

Reviewed on Mar 1, 2026

Where to stay in Island Estate

Find the best Island Estate areas and neighborhoods for the activities you enjoy most. Learn more about Island Estate

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.

Island Estate Hotel Deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

$397 nightly

$448 total

Apr 1 - Apr 2

Total with taxes and fees

9.4/10 Exceptional! (3,049 reviews)

Perfect view

Reviewed on Mar 9, 2026

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! (1,669 reviews)

Excellent. Start to finish.

Reviewed on Mar 10, 2026

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$344 nightly

$388 total

Mar 24 - Mar 25

Total with taxes and fees

8/10 Very Good! (2,493 reviews)

Direct access to beach, private beach and great location to local activities, shops and attractions!

Reviewed on Mar 10, 2026

See all 14,046 properties in Island Estate

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.

Discover the most popular places to visit in Island Estate

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.

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

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.

Florida. St Pete Beach FL. Summer vacations. Ocean beach, Hotels and Resorts in US. Blue-turquoise color of salt water. American Coast or shore line in Gulf of Mexico. St Petersburg Clearwater Florida

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

Nothing says vacation like spending a carefree day at St. Petersburg - Clearwater Beaches, a popular beach in St. Petersburg - Clearwater.

Clearwater Beach

4.5/5(44 reviews)

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.

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

$37

per adult

92% of travellers recommend

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$37

per adult

90% of travellers recommend

Little Toot Dolphin Adventure at Clearwater Beach

$37

per adult

96% of travellers recommend

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.

Island Estate Vacations from $617

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Island Estate Vacation

The Latest Island Estate Vacation Packages

Hibiscus Suites - Gateway to Siesta Key

voco Sarasota by IHG

Arvilla

The Fold Hotels Indian Shores

Where to stay in Island Estate

Downtown St. Petersburg

Pass-a-Grille

Sand Key

Sunshine Beach

Sunset Beach

Island Estate Hotel Deals

Wyndham Grand Clearwater Beach

RumFish Beach at TradeWinds

Hilton Clearwater Beach Resort & Spa

Discover the most popular places to visit in Island Estate

John's Pass Village & Boardwalk

St. Petersburg - Clearwater Beaches

Clearwater Beach

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

StarLite Majesty Evening Yacht Cruise Clearwater

Little Toot Dolphin Adventure at Clearwater Beach