Island Estate Holidays from NZ$2,485

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Top Holiday Package Deals in Island Estate

Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
North Trail
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Tampa (TPA)
8.4/10 Very Good! (2,072 reviews)
Stayed here multiple times, one of my favorite places to stay in the area. There were a couple issues in the room I had. The deadbolt did not lock and did not feel safe, woke up after my first night to the door ajar. There were stains on the towels and shower curtain. I notified the front desk when I checked out and was told a manager would contact me and have yet to hear from someone.

Reviewed on 12 Aug. 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Tampa (TPA)
8.2/10 Very Good! (1,345 reviews)
Needs some upgrades on current rooms, but we had a great stay there

Reviewed on 11 Aug. 2025

Carlisle Inn

Carlisle Inn

3.5 out of 5
Pinecraft
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Tampa (TPA)
10/10 Exceptional! (1,949 reviews)
Best breakfast and coffee!!

Reviewed on 12 Aug. 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Tampa (TPA)
9/10 Wonderful! (4,221 reviews)
Room was nice. Staff was nice. I wish they had a smoking area instead of having to stand outside the gate

Reviewed on 12 Aug. 2025

Hollander Boutique Hotel

Hollander Boutique Hotel

3 out of 5
Downtown St. Petersburg
per person
16 Sept - 21 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Tampa (TPA)
9.4/10 Exceptional! (2,012 reviews)
Close to downtown, nice pool area with bar

Reviewed on 12 Aug. 2025

Our guide on 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
Default Image

Pass-a-Grille

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Our pick of the best Island Estate Hotel Deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
The price is NZ$299 per night from 29 Aug to 30 Aug
NZ$299
29 Aug - 30 Aug
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Very good experience I love it there"

Reviewed on 11 Aug. 2025

The Westin Tampa Bay
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is NZ$382 per night from 17 Aug to 18 Aug
NZ$382
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"Sam the pool bartender made this stay 10 times better. He’s the best resource for finding any local recommendations."

Reviewed on 9 Aug. 2025

Grand Hyatt Tampa Bay
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
The price is NZ$372 per night from 18 Aug to 19 Aug
NZ$372
18 Aug - 19 Aug
includes taxes & fees
8/10 Very Good! (2,104 reviews)
"The access to the beach was the highlight of my trip… I also enjoyed the view from the balcony of my room."

Reviewed on 10 Aug. 2025

Hilton Clearwater Beach Resort & Spa
See all 13,440 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.

Frequently asked questions

How much does an Island Estate holiday package cost?
Go from looking to booking with our Island Estate holiday packages, which start from a low NZ$2,485. Choose the flights and hotels that suit your travel plans. Then, add on some sightseeing tours to round off your unique adventure.
How do I get a cheap travel package to Island Estate?
Combine your bookings with Expedia to save on your next getaway. With more than 550 airlines and 1 000 000 properties worldwide, your Island Estate holiday package can be customized exactly to suit your travel style. With all those extra dollars, why not throw in some awesome tours and activities? It's an easy way to unlock even more bargains. Your dream holiday in Island Estate is much closer than you thought!
Where should I stay in Island Estate?
A journey to Island Estate isn't complete without stopping by Clearwater Marine Aquarium and Sand Key Park. Book somewhere right nearby so you can easily access these terrific tourist attractions.
What are the top hotels in Island Estate?
Get your holiday off to a good start by reserving a room at 818 Harbour Island - 4 Bedroom Condo. It's one of most popular properties in Island Estate. Another welcoming option is Starboard Clipper Cove #605 - 2 Bedroom Apts.
How far in advance should I book my Island Estate holiday?
Travellers are generally able to look up international fares on Expedia within 12 months of departure. Booking last minute? With a stroke of luck, it's still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Island Estate travel package include?
Flights, car rentals and hotels — we bring you the very best bargains. All you have to do is figure out your favourite combination. After you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to create an unforgettable Island Estate escape.
What should I know before booking an Island Estate travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with an Island Estate Expedia holiday package?
Yes, and with over 550 airlines to pick from around the world, you've got lots of choice. Take a look at the available options and find out which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Island Estate holiday package?
We totally understand — life sometimes gets in the way of your plans. If you've booked an Island Estate holiday package and have to cancel or change it, we're here to help. We recommend looking up our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to change your itinerary at no cost. If it's more than 24 hours, your airline, hotel or car rental company may charge a fee.

Discover the most popular places to visit in Island Estate

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area or visit its lively bars.

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.

Tropicana Field
Salvador Dali Museum featuring night scenes and modern architecture

Salvador Dali Museum

Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.

Salvador Dali Museum

Activities

35 inch Snook we caught in 1 foot of water behind Clearwater Beach

Fishing Adventure in Clearwater

NZ$997
per traveller
Fishing Adventure in Clearwater
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

NZ$53
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

NZ$61
per adult
94% 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.