Landmark Estates Vacations from $454

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Your Landmark Estates Vacation

Reserving a tailor-made Landmark Estates vacation package is a good way to know the ins and outs of this unique neighborhood. From its must-see spots to its little-known delights, you'll be sure to uncover something new. Wondering what to see during your trip to Landmark Estates? John Chesnut Sr Park and John Chesnut Sr. Park are just a couple of nearby attractions that shouldn't be missed. No matter what your dream Landmark Estates vacation may look like, you can make it a reality with Expedia.

The Latest Landmark Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $720, price is now $454 per person
$454
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (23 reviews)
Estuvimos dos noches en el hotel y nos gustó mucho, todo muy limpio lo mismo dentro de la habitación que en la piscina, la atención excelente, la playa super serca del hotel es solo cruzar la calle, está ubicado céntrico, una experiencia satisfactoria la esatacia, lo volvería a repetir!!!

Reviewed on Aug 31, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $937, price is now $517 per person
$517
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep 2, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was $1,180, price is now $724 per person
$724
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
Amazing customer service

Reviewed on Sep 5, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,108, price is now $680 per person
$680
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,069 reviews)
We had an excellent stay at The Westin Sarasota. The hotel is modern, luxurious, and beautifully designed. Our room was large, comfortable, and very well-appointed. The rooftop bar and pool are absolutely stunning, offering some of the best views in Sarasota. The location is perfect—just a short walk to the marina and many great restaurants, plus only a quick drive to Siesta Key and Bradenton Beach, both incredible spots for enjoying the Gulf Coast. The staff was consistently helpful and welcoming, making our stay even better. Overall, this is a true luxury hotel experience in Sarasota. We would definitely return and highly recommend it to anyone visiting the area.

Reviewed on Sep 6, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,220, price is now $769 per person
$769
per person
Nov 6 - Nov 10
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (446 reviews)
Nice. On the beach. Provided chairs, toys, and umbrellas for the beach daily. Perfect for families. Only con is there are no guest showers and late check outs are not avaliable. If you want to visit the beach on your last day there is no where for you to shower and change before heading to the airport. Our entire family of six was cramed into the second floor restroom with our luggage changing clothes. The floor was full of sand when we entered the restroom so it seems like everyone does the same thing. Would I stay there again ? Yes.

Reviewed on Sep 6, 2025

Where to stay in Landmark Estates

Find the best Landmark Estates areas and neighborhoods for the activities you enjoy most. Learn more about Landmark Estates
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

Landmark Estates Hotel Deals

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
$204 nightly
The price is $231 total per night from Sep 14 to Sep 15
$231 total
Sep 14 - Sep 15
Total with taxes and fees
Hilton Clearwater Beach Resort & Spa
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $156 total per night from Sep 7 to Sep 8
$156 total
Sep 7 - Sep 8
Total with taxes and fees
Hilton Tampa Airport Westshore
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $227 total per night from Sep 7 to Sep 8
$227 total
Sep 7 - Sep 8
Total with taxes and fees
Grand Hyatt Tampa Bay
See all 12,705 properties in Landmark Estates
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 Landmark Estates

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 check out its lively bars.

John's Pass Village & Boardwalk
The sunset behind the lifeguard tower in combination with a bit of filtering made this image quite unique. #LifeAtExpedia

Clearwater Beach

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
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

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 StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
88% 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
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.