Island Estate Vacations from $710

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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 $1,157, price is now $710 per person
$710
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,002 reviews)
Location and friendly staff..

Reviewed on Mar 1, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,638, price is now $993 per person
$993
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,185 reviews)
Helpful staff; room was very humid and smelled a bit.

Reviewed on Mar 2, 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 $1,271, price is now $774 per person
$774
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (530 reviews)
All of those and the wonderful, helpful staff

Reviewed on Feb 19, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,350, price is now $833 per person
$833
per person
May 27 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (837 reviews)
Very clean. Nice staff

Reviewed on Mar 5, 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
$326 nightly
The price is $368 total per night from Mar 25 to Mar 26
$368 total
Mar 25 - Mar 26
Total with taxes and fees
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 10 to Mar 11
$417 total
Mar 10 - Mar 11
Total with taxes and fees
8.2/10 Very Good! (1,657 reviews)
Room was nicely furnished. Glad we stayed in the upgraded room.

Reviewed on Mar 5, 2026

RumFish Beach at TradeWinds
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $445 total per night from Mar 8 to Mar 9
$445 total
Mar 8 - Mar 9
Total with taxes and fees
7.6/10 Good! (1,028 reviews)
Beautiful

Reviewed on Mar 5, 2026

Island Grand at TradeWinds
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 marina 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.