Island Estate Vacations from $504

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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.
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $786, price is now $504 per person
$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

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was $833, price is now $528 per person
$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

Arvilla

2 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,038, price is now $657 per person
$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

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $969, price is now $622 per person
$622
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,056 reviews)
Good mattresses, clean rooms, friendly, helpful staff Needs laundry facilities

Reviewed on Mar 11, 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 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

Island Estate 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
$404 nightly
The price is $456 total per night from Apr 5 to Apr 6
$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

Wyndham Grand Clearwater Beach
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
$360 nightly
The price is $407 total per night from Mar 22 to Mar 23
$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

RumFish Beach at TradeWinds
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
$313 nightly
The price is $354 total per night from Mar 24 to Mar 25
$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

Hilton Clearwater Beach Resort & Spa
See all 13,889 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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

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.

John's Pass Village & Boardwalk
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

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

St. Petersburg - Clearwater Beaches
White sand and palm trees in 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

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$37
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

$37
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.