Island Estate Vacations from $340

Book a Hotel + Flight or Car together to unlock savings

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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $577, price is now $340 per person
$340
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.

Reviewed on Oct 4, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $3,548, price is now $1,861 per person
$1,861
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Very nice clean rooms with a lot of amenities for guests! Will definitely stay here again! Thank you Karen!

Reviewed on Oct 11, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,737, price is now $972 per person
$972
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
The place is great, excellent location, close to many outdoor activities, amazing ocean view, staff is very good and attentive to our needs, hotel is clean, parking very convenient, rooms are very nice, clean and confortable. We’ll definitely come back and recommend Ocean Club.

Reviewed on Oct 13, 2025

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
Price was $2,137, price is now $1,418 per person
$1,418
per person
Dec 27 - Jan 3
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,003 reviews)
Staff are wonderful. Rooms and the buildings are a little outdated but still clean. Overall a wonderful experience.

Reviewed on Oct 8, 2025

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was $1,038, price is now $690 per person
$690
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (387 reviews)
Seven night stay, staff was friendly and helpful, room was clean and comfortable. Would stay there anytime!

Reviewed on Oct 13, 2025

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

Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,017 reviews)
"Quiet, comfortable, nice gym"

Reviewed on Oct 8, 2025

Hilton Tampa Airport Westshore
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
$215 nightly
The price is $242 total per night from Oct 20 to Oct 21
$242 total
Oct 20 - Oct 21
Total with taxes and fees
8/10 Very Good! (2,246 reviews)
"Right on the beach with excellent amenities"

Reviewed on Oct 11, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Oct 24 to Oct 25
$148 total
Oct 24 - Oct 25
Total with taxes and fees
8.6/10 Excellent! (2,262 reviews)
"Rooms were clean. Staff was friendly and hotel is just a great place to stay."

Reviewed on Oct 12, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 13,681 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

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

John's Pass Village & Boardwalk
Clearwater Beach

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.

Clearwater Beach
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

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

$37
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.