Island Estate Vacations from $542

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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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $816, price is now $542 per person
$542
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,088 reviews)
This was a very nice hotel, the staff was exceptional. The only reason I didn’t give a 5 star rating is there is no coffee maker in the rooms. I had never stayed at a hotel that didn’t have coffee in my room. I went down to the lobby and had to pay $3.11 for a tiny cup of coffee.

Reviewed on Mar 15, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,658, price is now $994 per person
$994
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (838 reviews)
I loved having everything ready to use. I do love the proximity of the beach. We have small children so the pool was great as well not too cold at all. The view was gorgeous!!! Lots of really nice people and patient people at the resort.

Reviewed on Mar 14, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $1,934, price is now $1,212 per person
$1,212
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,135 reviews)
The pool was the highlight of the stay...it was warm ..hot tub was great and deck area was great...only downside seemed to always out or low on towels....All staff were very friendly. Air conditioning was freat since it was 80 to 85 degrees all week...

Reviewed on Mar 12, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,526, price is now $1,003 per person
$1,003
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,003 reviews)
Everything was wonderful!! Walls a little thin as we could hear neighbor's all hours of the night. Otherwise i had a wonderful experience.

Reviewed on Mar 14, 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 $1,185, price is now $783 per person
$783
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)
Our stay was amazing! Great staff, the ladies in the lobby was friendly and polite. The shuttle driver was amazing! Great hotel in a great location 10/10 I will be back😊

Reviewed on Mar 9, 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

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
$410 nightly
The price is $464 total per night from Apr 12 to Apr 13
$464 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (3,072 reviews)
We had a gulf-front room, so the view of the beach & ocean was great. Noise from the street and other events could be a bit however, the patio doors/windows were pretty solid so not a lot of noise got inside the room. Staff was great, helpful and friendly. Nice location. Pricey, for one, i don't ...

Reviewed on Mar 15, 2026

Wyndham Grand Clearwater Beach
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
$309 nightly
The price is $349 total per night from Mar 22 to Mar 23
$349 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (1,681 reviews)
Rum Fish, Clean rooms, however outdated. Beach wonderful, beach staff great! Pool bar lines were long wait times.

Reviewed on Mar 15, 2026

RumFish Beach at TradeWinds
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
$273 nightly
The price is $308 total per night from Mar 22 to Mar 23
$308 total
Mar 22 - Mar 23
Total with taxes and fees
8.2/10 Very Good! (2,495 reviews)
Hilton was beautiful! You couldn’t ask for a better location right on the beach and 2 pools. You could walk to shops, restaurants, the park and pier. Staff went above and beyond every day! We actually booked extra days because we loved it so much!

Reviewed on Mar 15, 2026

Hilton Clearwater Beach Resort & Spa
See all 13,889 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
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
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

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.