Island Estate Vacations from $558

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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.
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
Price was $802, price is now $558 per person
$558
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
8.4/10 Very Good! (525 reviews)
This is a quiet property

Reviewed on Apr 1, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was $1,196, price is now $763 per person
$763
per person
Jun 14 - Jun 20
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9/10 Wonderful! (1,012 reviews)
Room was very clean.

Reviewed on Mar 29, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,596, price is now $1,020 per person
$1,020
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (846 reviews)
Place was amazing. We can’t wait to come back. Everything was perfect.

Reviewed on Mar 30, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,371, price is now $932 per person
$932
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,012 reviews)
Too expensive for the amenities, they charge 45 dollats for self parking and the pool is really small. The beach is not privately

Reviewed on Mar 30, 2026

Arvilla

Arvilla

2 out of 5
Sunshine Beach
Save 100% on your flight
Price was $916, price is now $637 per person
$637
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
7.6/10 Good! (44 reviews)
Cute and clean little place. Had everything we needed and the mattress was AWESOME.

Reviewed on Mar 30, 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
Pass-a-Grille

Pass-a-Grille

5/5(26 area reviews)

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

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
$254 nightly
The price is $287 total per night from Apr 12 to Apr 13
$287 total
Apr 12 - Apr 13
Total with taxes and fees
8.2/10 Very Good! (1,744 reviews)
Chris at front desk was terrible and rude.

Reviewed on Apr 1, 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
$366 nightly
The price is $414 total per night from Apr 21 to Apr 22
$414 total
Apr 21 - Apr 22
Total with taxes and fees
9.4/10 Exceptional! (3,104 reviews)
Nice place. Needs more character or culture. Very peaceful. Good for quiet relaxation.

Reviewed on Apr 1, 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
$281 nightly
The price is $317 total per night from Apr 12 to Apr 13
$317 total
Apr 12 - Apr 13
Total with taxes and fees
Hilton Clearwater Beach Resort & Spa
See all 14,225 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(1,653 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(47 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

Sunset Celebration Cruise on Tropics Boat Tours

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.