Island Estate Vacations from $427

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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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $948, price is now $427 per person
$427
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Excellent customer service

Reviewed on Dec 14, 2025

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $1,036, price is now $480 per person
$480
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
No reviews
SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $992, price is now $566 per person
$566
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (432 reviews)
I didn’t know about the $50 resort fee! Place is great!

Reviewed on Dec 10, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,856, price is now $1,108 per person
$1,108
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
This place was a great surprise ! So friendly so helpful ! Great location and rooms super clean . Tons of amenities too! Will definitely stay again

Reviewed on Dec 8, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $2,546, price is now $1,536 per person
$1,536
per person
Mar 4 - Mar 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
Very good hotel close to everything

Reviewed on Dec 21, 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

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
$241 nightly
The price is $272 total per night from Jan 1 to Jan 2
$272 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.4/10 Exceptional! (2,916 reviews)
Staff was amazing! Thank you!

Reviewed on Dec 21, 2025

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
$190 nightly
The price is $215 total per night from Jan 11 to Jan 12
$215 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8/10 Very Good! (2,360 reviews)
Great hotel, awesome views, friendly staff

Reviewed on Dec 15, 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
$134 nightly
The price is $152 total per night from Dec 27 to Dec 28
$152 total
Dec 27 - Dec 28
Total with taxes and fees
8.6/10 Excellent! (2,458 reviews)
The hotel in all is fantastic. I recommend this hotel to anyone who is looking for a great place to relax ,and enjoy the amenities and people.

Reviewed on Dec 21, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 13,865 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

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the marina 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 StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$29
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$32
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$31
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.