Baileys Bluff Estates Vacations from $454

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Your Baileys Bluff Estates Vacation

Discover all the amazing things this neighborhood has to offer with a customized Baileys Bluff Estates vacation package. However you imagine spending your time here, you'll find endless opportunities for adventure, relaxation and fun. Not sure what to see and do during your trip to Baileys Bluff Estates? Nearby attractions like Anclote River Park, Key Vista Nature Park and Anclote Gulf Park are great places to start. Expedia can help you turn your dream Baileys Bluff Estates vacation into reality, no matter your budget or travel plans.

The Latest Baileys Bluff Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express St. Petersburg North (I-275) by IHG

Holiday Inn Express St. Petersburg North (I-275) by IHG

2.5 out of 5
Lealman
Price was $806, price is now $454 per person
$454
per person
Jan 5 - Jan 12
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (1,006 reviews)
Great service and clean property.

Reviewed on Oct 29, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,185, price is now $1,721 per person
$1,721
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (466 reviews)
Overall the property was clean; however, it was a great disappointment to see the street light with wires as an ocean view literally right outside your balcony. I also didn’t appreciate upon greeting the staff stressed about the fees instead of stressing what is already included, such as the beach chairs, umbrella etc…

Reviewed on Oct 15, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,891, price is now $1,039 per person
$1,039
per person
Jan 5 - Jan 12
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (669 reviews)
Very clean, and quiet.

Reviewed on Oct 31, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,074, price is now $590 per person
$590
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4,474 reviews)
I had an enjoyable stay at the hotel, and I would like to make some recommendations to make it more enjoyable. It would be really nice if the breakfast buffet had a fresh fruit salad, strawberries, bananas, plain yogurt vs sweetened and also boiled or poached eggs vs just the scrambled eggs from a box.

Reviewed on Nov 3, 2025

The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Price was $1,017, price is now $563 per person
$563
per person
Jan 5 - Jan 12
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (129 reviews)
Everything seems brand new and clean, very easy check-in process, amazing sunset views, we will definitely be back!

Reviewed on Oct 31, 2025

Where to stay in Baileys Bluff Estates

Find the best Baileys Bluff Estates areas and neighborhoods for the activities you enjoy most. Learn more about Baileys Bluff Estates
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Key Vista

If you're looking for some top things to see and do in Key Vista and surrounding area, you can visit Anclote River Park and Tarpon Springs Sponge Docks.

Find hotels in Key Vista

Baileys Bluff Estates Hotel Deals

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
$261 nightly
The price is $295 total per night from Nov 23 to Nov 24
$295 total
Nov 23 - Nov 24
Total with taxes and fees
9.4/10 Exceptional! (2,766 reviews)
Excellent accommodation, staff were friendly & so helpful.

Reviewed on Oct 27, 2025

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
$215 nightly
The price is $242 total per night from Nov 17 to Nov 18
$242 total
Nov 17 - Nov 18
Total with taxes and fees
8/10 Very Good! (2,285 reviews)
The room was spotless and the staff was really courteous

Reviewed on Nov 1, 2025

Hilton Clearwater Beach Resort & Spa
JW Marriott Clearwater Beach Resort & Spa

JW Marriott Clearwater Beach Resort & Spa

4 out of 5
691 S Gulfview Blvd, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$334 nightly
The price is $377 total per night from Nov 19 to Nov 20
$377 total
Nov 19 - Nov 20
Total with taxes and fees
9.2/10 Wonderful! (293 reviews)
nice views

Reviewed on Oct 28, 2025

JW Marriott Clearwater Beach Resort & Spa
See all 4,459 properties in Baileys Bluff 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 Baileys Bluff Estates

Lovely isolated spot with white sands and Gulf waters as far as the eye can see #wanderlust #Florida

Key Vista Nature Park

Commune with nature and explore the great outdoors at Key Vista Nature Park during your travels in Holiday. Stroll along the waterfront in this family-friendly area, or seek out the golf courses.

Key Vista Nature Park

Anclote River Park

Why not spend a carefree afternoon at Anclote River Park during your travels in Holiday? While you're in the area, wander around the parks.

Anclote River Park

Anclote Gulf Park

Anclote Gulf Park is just one of the places to see in Holiday, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's waterfront, or seek out the golf courses.

Anclote Gulf Park

Things to do

2 Hours Kayak Eco Tour in Tarpon Springs

2 Hours Kayak Eco Tour in Tarpon Springs

$54
per adult
2 Hours Kayak Eco Tour in Tarpon Springs
Spring Bayou

Tarpon Springs Ghost & History Tour by Silent Slayer Ghost Tours

$40
per adult
Tarpon Springs Ghost & History Tour by Silent Slayer Ghost Tours
Sponge Dock Stroll

Sponge Dock Stroll

$52
per adult
100% of travellers recommend
Sponge Dock Stroll
See all activities in Holiday
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.