Island Estate Vacations from $532

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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
Save 100% on your flight
Price was $857, price is now $532 per person
$532
per person
Jun 10 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
Nice old Florida feel motel Clean room parking in front of unit Receive code to the room early and very easy to use !!!! Two night stay with my sister Close to everything and quiet Would stay here again

Reviewed on Mar 19, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,253, price is now $764 per person
$764
per person
May 23 - May 30
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

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,134, price is now $729 per person
$729
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,193 reviews)
The hotel is beautiful, the rooms are clean, and the staff are very friendly. I love the rooftop.

Reviewed on Mar 19, 2026

Arvilla

Arvilla

2 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,034, price is now $676 per person
$676
per person
May 31 - Jun 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
7.6/10 Good! (44 reviews)
Beautiful old school Florida motel. Recently renovated. Easy check in and out.

Reviewed on Mar 7, 2026

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
Price was $1,165, price is now $770 per person
$770
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,571 reviews)
The property was very pretty and conveniently located to Raymond James stadium. The shuttle was free to go to the stadium for a concert . The staff were very friendly and helpful and the rooms were updated and decorated nicely.

Reviewed on Mar 19, 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

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
$320 nightly
The price is $362 total per night from Apr 19 to Apr 20
$362 total
Apr 19 - Apr 20
Total with taxes and fees
8.4/10 Very Good! (1,702 reviews)
On the 5th floor, elevator went down entire trip. Moved us to a ground floor, which was nice but unit was dirty. Great family oriented resort, needs more bodies to accommodate size of property.

Reviewed on Mar 19, 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
$391 nightly
The price is $442 total per night from Apr 12 to Apr 13
$442 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (3,075 reviews)
Beautiful property with direct views of Clearwater Beach which is just across the street. Watched dolphins from our hotel balcony. Excellent for kids with several activities scheduled throughout the day for school aged kids to attend (held in the pool area). Pool was warm, hot tub is large and the ...

Reviewed on Mar 19, 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
$325 nightly
The price is $368 total per night from Mar 24 to Mar 25
$368 total
Mar 24 - Mar 25
Total with taxes and fees
8.2/10 Very Good! (2,495 reviews)
The first room was not clean… moved us and then every day left us with no towels or body wash snd soap

Reviewed on Mar 18, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,014 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

4.5/5(1,631 reviews)

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

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
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

4.5/5(6 reviews)

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