Island Estate Vacations from $557

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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $830, price is now $557 per person
$557
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,012 reviews)
We enjoyed our stay at vocoSarasota.. The best part was the amazing and very accommodating staff especially the Shuttle drivers Rich, Barry and Cody. they were terrific. Rooms were very nice. I just wished they had better outdoor accomodations especially the pool area.The daily breakfast was good even when the chef had to be the Manager on duty. Just a few hiccups with that. overall it was a delightful stay and the location was perfect!!!!

Reviewed on Mar 17, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,788, price is now $1,156 per person
$1,156
per person
May 9 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (846 reviews)
We enjoyed the pool area. Hotel was very quite, and very clean

Reviewed on Mar 24, 2026

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $965, price is now $624 per person
$624
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
The property was perfect for pets. Big space to walk and off the main road.

Reviewed on Mar 23, 2026

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,687, price is now $1,171 per person
$1,171
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (515 reviews)
Our family had a wonderful 4-night stay at this well kept hotel. The apartment was spacious, very clean, had nice amenities, and the hotel is conveniently located just steps from the beach. We recommend and would be happy to stay there again.

Reviewed on Mar 13, 2026

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $953, price is now $664 per person
$664
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,126 reviews)
Great price typical morning buffet with a little upgrade. Lobby was inviting and people really did just relax there. Pool is nothing special. Kitchen had reasonable prices and variety for all kinds of tastes.

Reviewed on Mar 27, 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

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

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
$263 nightly
The price is $297 total per night from Apr 12 to Apr 13
$297 total
Apr 12 - Apr 13
Total with taxes and fees
8.2/10 Very Good! (1,729 reviews)
Didn't have beach view ! Had to pay $100 more for a room that had a slider that could not be open ! Beach is beautiful ! Place was a dump ! Very disappointed !

Reviewed on Mar 27, 2026

RumFish Beach at TradeWinds
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
$385 nightly
The price is $435 total per night from Apr 16 to Apr 17
$435 total
Apr 16 - Apr 17
Total with taxes and fees
9.4/10 Exceptional! (3,084 reviews)
Beautiful property with a very friendly and welcoming staff. The only reason for the 4-star rating is that the rooms could use a bit of a refresh - our carpet felt a bit damp. With some room updates, such as wood / vinyl flooring, this would be a 5-star experience.

Reviewed on Mar 26, 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
$328 nightly
The price is $371 total per night from Apr 12 to Apr 13
$371 total
Apr 12 - Apr 13
Total with taxes and fees
8.2/10 Very Good! (2,508 reviews)
The staff was friendly and property was well kept.

Reviewed on Mar 26, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,060 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

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

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
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
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

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

Sunset Celebration Cruise on Tropics Boat Tours

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.