Island Estate Vacations from $484

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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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $711, price is now $484 per person
$484
per person
Jun 4 - Jun 8
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
The property was perfect for pets. Big space to walk and off the main road.

Reviewed on Mar 23, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $878, price is now $578 per person
$578
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,012 reviews)
We enjoyed our stay at vocoSarasota.. The best part was the amazing and very accommodating staff especially the Shuttle drivers Rich, Barry and Cody. they were terrific. Rooms were very nice. I just wished they had better outdoor accomodations especially the pool area.The daily breakfast was good even when the chef had to be the Manager on duty. Just a few hiccups with that. overall it was a delightful stay and the location was perfect!!!!

Reviewed on Mar 17, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $2,013, price is now $1,365 per person
$1,365
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
9.2/10 Wonderful! (1,141 reviews)
The room was cool with an excellent view.

Reviewed on Mar 23, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,192, price is now $830 per person
$830
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (846 reviews)
This hotel has beautiful views of the beach. The rooms are really nice and spacious too.

Reviewed on Mar 23, 2026

Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
Save 100% on your flight
Price was $2,054, price is now $1,436 per person
$1,436
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.6/10 Good! (1,038 reviews)
The villa was spacious. But its an old property no matter

Reviewed on Mar 19, 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

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
$282 nightly
The price is $319 total per night from Apr 19 to Apr 20
$319 total
Apr 19 - Apr 20
Total with taxes and fees
8.2/10 Very Good! (1,710 reviews)
Great place for families to vacation

Reviewed on Mar 22, 2026

RumFish Beach at TradeWinds
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
$385 nightly
The price is $435 total per night from Apr 16 to Apr 17
$435 total
Apr 16 - Apr 17
Total with taxes and fees
9.4/10 Exceptional! (3,080 reviews)
Very close to many stores, restaurants and the marina. Loved the pool and hot tub. It was very well maintained and clean. Easy walk to beach with chairs and umbrella already set up. Great having pool towels available. Beautiful hotel and beach.

Reviewed on Mar 23, 2026

Wyndham Grand Clearwater Beach
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
$301 nightly
The price is $340 total per night from Mar 26 to Mar 27
$340 total
Mar 26 - Mar 27
Total with taxes and fees
8.2/10 Very Good! (2,505 reviews)
Pool and Beach were great.

Reviewed on Mar 23, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,014 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

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

4.5/5(1,631 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
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
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

4.5/5(6 reviews)

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

St. Petersburg - Clearwater Beaches

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.