Island Estate Vacations from $277

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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.
Hampton Inn Sarasota - I-75 Bee Ridge

Hampton Inn Sarasota - I-75 Bee Ridge

2.5 out of 5
Save 100% on your flight
Price was $480, price is now $277 per person
$277
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
17.2/10 Exceptional! (317 reviews)
Clean , goof location, comfortable beds

Reviewed on Nov 18, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,267, price is now $689 per person
$689
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
18.8/10 Exceptional! (481 reviews)
Excellent staff. Very clean, spacious, great location

Reviewed on Nov 17, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $609, price is now $332 per person
$332
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
16.4/10 Exceptional! (1,002 reviews)
Yes, the staff was very courteous and accommodating. The lobby was bright and clean. . The room was clean and roomie very comfortable. The pool was clean and the hot tub was so relaxing. Breakfast each morning was consistently delicious and even a beautiful presentation liked having the convenience of purchasing products right on the site.

Reviewed on Nov 20, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $556, price is now $327 per person
$327
per person
Jan 30 - Feb 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
18.4/10 Exceptional! (4,624 reviews)
JULIO was so professional and belpful

Reviewed on Nov 20, 2025

Arvilla

Arvilla

2 out of 5
Sunshine Beach
Save 100% on your flight
Price was $886, price is now $553 per person
$553
per person
Feb 6 - Feb 10
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
14.4/10 Exceptional! (24 reviews)
Beautiful spacious room. Quick walk to the waters edge. Very helpful ataff

Reviewed on Nov 18, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
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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

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W Tampa FL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Nov 25 to Nov 26
$139 total
Nov 25 - Nov 26
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Room was clean and very quiet, with very comfortable beds and very fast internet connection. Convenient location for our agenda in Tampa.

Reviewed on Nov 17, 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront
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
$177 nightly
The price is $200 total per night from Dec 1 to Dec 2
$200 total
Dec 1 - Dec 2
Total with taxes and fees
9.4/10 Exceptional! (2,806 reviews)
Little expensive but great experience

Reviewed on Nov 14, 2025

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
$166 nightly
The price is $188 total per night from Dec 14 to Dec 15
$188 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (1,516 reviews)
All good

Reviewed on Nov 15, 2025

RumFish Beach at TradeWinds
See all 13,883 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

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches
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
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.