Baileys Bluff Estates Vacations from $350

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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.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $559, price is now $350 per person
$350
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip 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

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,259, price is now $713 per person
$713
per person
Oct 6 - Oct 12
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

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,033, price is now $624 per person
$624
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,600 reviews)
Great place to stay

Reviewed on Sep 6, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $788, price is now $478 per person
$478
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

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,021, price is now $622 per person
$622
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip 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 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

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
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
$286 nightly
The price is $323 total per night from Sep 7 to Sep 8
$323 total
Sep 7 - Sep 8
Total with taxes and fees
Wyndham Grand Clearwater Beach
Opal Sands Resort

Opal Sands Resort

4 out of 5
430 South Gulfview Blvd, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$330 nightly
The price is $373 total per night from Sep 7 to Sep 8
$373 total
Sep 7 - Sep 8
Total with taxes and fees
Opal Sands Resort
See all 4,456 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

Tarpon Springs Train Depot at Night

Tarpon Springs: Ghost and Haunted History Tour

$40
per adult
Tarpon Springs: Ghost and Haunted History Tour
Goodacre's "Naiads" at the Sponge Docks

I Came, I Saw... I GREEKED!

$165
per adult
I Came, I Saw... I GREEKED!
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
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.