Landmark Estates Vacations from $477

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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $787, price is now $477 per person
$477
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip 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 $821, price is now $493 per person
$493
per person
Nov 8 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
We were very pleased with our 3 night stay at the hotel. The staff graciously offered us an umbrella and chairs to take to the beach from the donation stash. We really appreciated that and returned the items when we left for future guests.

Reviewed on Sep 8, 2025

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney

3.5 out of 5
Save 100% on your flight
Price was $843, price is now $532 per person
$532
per person
Nov 11 - Nov 18
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
Shephard's Beach Resort

Shephard's Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,021, price is now $665 per person
$665
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,394 reviews)
Beautiful with lots of amenities.

Reviewed on Sep 7, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $967, price is now $647 per person
$647
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,058 reviews)
Hands down one of the best hotels I’ve ever stayed at. Not only is it in a gorgeous location but the suite was incredible, the wine that was waiting for us in our room was phenomenal and the amenities were wonderful. They offer bikes for free as part of your stay, and me and my daughter biked all around the island it was such a good day ☀️. Would absolutely recommend this place to anybody. Perfect for couples but also very family friendly too. Will be staying here again!!

Reviewed on Sep 7, 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 Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $153 total per night from Oct 5 to Oct 6
$153 total
Oct 5 - Oct 6
Total with taxes and fees
Hilton Tampa Airport Westshore
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 15 to Sep 16
$231 total
Sep 15 - Sep 16
Total with taxes and fees
Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $173 total per night from Sep 22 to Sep 23
$173 total
Sep 22 - Sep 23
Total with taxes and fees
Hotel Alba, Tapestry Collection by Hilton
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

4.5/5(1,625 reviews)

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

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
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

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.