Island Estate Vacations from $489

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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 $724, price is now $489 per person
$489
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,056 reviews)
We had a great stay at Kompose Boutique Hotel in Sarasota. Everything was clean, modern and very well organized. The staff was friendly and helpful during our entire stay. The breakfast was very good and nicely prepared every morning. It was a great way to start the day before going out. The location is also very convenient – it’s a short drive to the beaches and many restaurants nearby. Overall we were very happy with our stay and would definitely come back again. Thank you for the great hospitality!

Reviewed on Mar 10, 2026

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $876, price is now $552 per person
$552
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (530 reviews)
Staff were really friendly from front desk to bartenders to valet. Food was excellent and pool was nice with a fun vibe. Parts of hotel are dated and parts are newly renovated. It’s in a great location. I would return.

Reviewed on Mar 9, 2026

Arvilla

Arvilla

2 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,038, price is now $657 per person
$657
per person
May 16 - May 23
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.6/10 Good! (41 reviews)
Beautiful old school Florida motel. Recently renovated. Easy check in and out.

Reviewed on Mar 7, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,888, price is now $1,209 per person
$1,209
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,004 reviews)
Very friendly staff and clean rooms

Reviewed on Mar 9, 2026

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Save 100% on your flight
Price was $1,879, price is now $1,258 per person
$1,258
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,654 reviews)
Spring break trip…excellent beach and amenities. The staff was really friendly and the room was a great size for 4.

Reviewed on Mar 8, 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
$404 nightly
The price is $456 total per night from Apr 5 to Apr 6
$456 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (3,067 reviews)
Perfect view

Reviewed on Mar 9, 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
$369 nightly
The price is $417 total per night from Mar 11 to Mar 12
$417 total
Mar 11 - Mar 12
Total with taxes and fees
8.4/10 Very Good! (1,666 reviews)
Clean room nice upgrade

Reviewed on Mar 9, 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
$342 nightly
The price is $387 total per night from Mar 23 to Mar 24
$387 total
Mar 23 - Mar 24
Total with taxes and fees
8/10 Very Good! (2,491 reviews)
Great view of the pier from the room.

Reviewed on Mar 10, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,046 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.