Island Estate Vacations from $435

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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 $644, price is now $435 per person
$435
per person
May 10 - May 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good!

Reviewed on Feb 26, 2026

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,009, price is now $648 per person
$648
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,088 reviews)
The room was very clean

Reviewed on Mar 17, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,851, price is now $1,209 per person
$1,209
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,141 reviews)
Everything was wonderful

Reviewed on Mar 16, 2026

Arvilla

Arvilla

2 out of 5
Sunshine Beach
Price was $1,046, price is now $711 per person
$711
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Crystal Palms Beach Resort

Crystal Palms Beach Resort

4 out of 5
Sunshine Beach
Price was $1,616, price is now $1,108 per person
$1,108
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4 reviews)
There was construction going on all around us, and it was very loud when I was trying to take a nap. Aside from the sound, there was plastic and tape everywhere and furniture blocking the hallway. The elevators were slow as ever, and at one point I thought we were stick because the doors wouldn't open. But despite all this, the worst part was the mattress in each room.. both my boyfriend and I had very sore backs after night 1.. and he ended up sleeping on the couch for nights 2 and 3.. while I just suffered through it since there was nowhere else. All in all, it was not the best experience. But the balcony was huge and the view was nice.

Reviewed on Mar 15, 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
$339 nightly
The price is $383 total per night from Mar 23 to Mar 24
$383 total
Mar 23 - Mar 24
Total with taxes and fees
8.4/10 Very Good! (1,694 reviews)
Old and needs updating for the cost we paid to stay.

Reviewed on Mar 17, 2026

RumFish Beach at TradeWinds
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
$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! (3,072 reviews)
Great

Reviewed on Mar 17, 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
$319 nightly
The price is $361 total per night from Mar 25 to Mar 26
$361 total
Mar 25 - Mar 26
Total with taxes and fees
8.2/10 Very Good! (2,501 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(1,625 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the 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

5/5(5 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.