Island Estate Vacations from $406

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $607, price is now $406 per person
$406
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,002 reviews)
Location and friendly staff..

Reviewed on Mar 1, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,326, price is now $811 per person
$811
per person
May 25 - May 30
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

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $794, price is now $520 per person
$520
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,056 reviews)
A refurbished old office building but still an acceptable place to stay

Reviewed on Mar 4, 2026

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $739, price is now $505 per person
$505
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (60 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

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,742, price is now $1,223 per person
$1,223
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Gym was well equipped and spacious, rooms were clean, kitchenette had all the things you would need, staff was super friendly and accommodating, and they have beach stuff that you can check out for free which was such a nice surprise. Plus the location is minutes from the beach with a rooftop view you can’t beat!

Reviewed on Mar 2, 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
9.4/10 Exceptional! (3,057 reviews)
Great beach view. Walking distance to many bars and restaurants. Staff was great!

Reviewed on Mar 5, 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 10 to Mar 11
$417 total
Mar 10 - Mar 11
Total with taxes and fees
8.2/10 Very Good! (1,656 reviews)
Beach view was great. Staff was friendly. Food at the resort was very good.

Reviewed on Mar 4, 2026

RumFish Beach at TradeWinds
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $202 total per night from Apr 5 to Apr 6
$202 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (1,148 reviews)
My stay here was great as I was initially disappointed, the hotel I usually frequent was not available. This was my first time at this location and I was pleasantly surprised! The gym was clean and had useful equipment. The onsite restaurant and bar were very nice and accommodating not to mention ...

Reviewed on Mar 4, 2026

The Westin Tampa Bay
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.