Island Estate Vacations from $403

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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.
Zoo House Down Town Tampa

Zoo House Down Town Tampa

2.5 out of 5
Riverbend
Price was $728, price is now $403 per person
$403
per person
Mar 26 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
2/10 (1 review)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $1,034, price is now $579 per person
$579
per person
Mar 21 - Mar 28
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
Great staff, very clean.

Reviewed on Jan 11, 2026

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,493, price is now $881 per person
$881
per person
Mar 21 - Mar 28
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Yes and staff were very courteous and helpful

Reviewed on Jan 17, 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,598, price is now $968 per person
$968
per person
Mar 21 - Mar 28
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (2,509 reviews)
Many rooms including mine had no hot water. Even though the issue was reported, nothing was done about it. Took one cold shower the entire stay.

Reviewed on Jan 12, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was $1,725, price is now $1,054 per person
$1,054
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Staff was very courteous

Reviewed on Jan 7, 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
$297 nightly
The price is $335 total per night from Jan 20 to Jan 21
$335 total
Jan 20 - Jan 21
Total with taxes and fees
9.2/10 Wonderful! (2,989 reviews)
Nice hotel with helpful staff

Reviewed on Jan 13, 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
$223 nightly
The price is $252 total per night from Jan 25 to Jan 26
$252 total
Jan 25 - Jan 26
Total with taxes and fees
8/10 Very Good! (2,401 reviews)
Location to the beach and restaurants was perfect. The property, rooms are ok.

Reviewed on Jan 11, 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
$82 nightly
The price is $93 total per night from Feb 8 to Feb 9
$93 total
Feb 8 - Feb 9
Total with taxes and fees
6.2/10 (3,792 reviews)
Room was clean, location was perfect for my needs, staff were friendly. The place shows its age, but that did not bother me.

Reviewed on Jan 16, 2026

Ramada by Wyndham Tampa Westshore Airport South
See all 13,926 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

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 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
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
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
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
90% 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.