Whitfield Estates Vacations from $655

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Your Whitfield Estates Vacation

Lock in a Whitfield Estates vacation package and get ready to experience the best of this city. Think about staying in the neighborhood of Village of the Arts, which is good for cafes, shopping and history. If your trip to Whitfield Estates includes some sightseeing, drop by well-known attractions like Mote Marine Laboratory & Aquarium, Marie Selby Botanical Gardens and Sarasota Jungle Gardens. Stop dreaming and start doing. Browse the broad range of options on Expedia today and put your Whitfield Estates vacation plans into gear!

The Latest Whitfield 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 $1,060, price is now $655 per person
$655
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.

Reviewed on Oct 4, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,296, price is now $1,310 per person
$1,310
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
The place is great, excellent location, close to many outdoor activities, amazing ocean view, staff is very good and attentive to our needs, hotel is clean, parking very convenient, rooms are very nice, clean and confortable. We’ll definitely come back and recommend Ocean Club.

Reviewed on Oct 13, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,638, price is now $1,634 per person
$1,634
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Resort and room were very clean. On the beach a huge bonus. Staff extremely friendly. Downsides: The phrase "Total includes taxes and fees" is not correct. Was hit with a resort and parking fee after booking. Unacceptable. Include them in final price or show "additional fees" prior to booking. Rooftop bar closes too early. Fitness center closes too early. Photo on website shows beautiful Adirondack chairs but resort gave out used/dirty beach chairs. Free towels were also quite harsh. Glad we brought our own. Bottom line - would stay here again but only when "added fees" are removed.

Reviewed on Oct 13, 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
South Village
Save 100% on your flight
Price was $1,235, price is now $766 per person
$766
per person
Jan 6 - Jan 12
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,132 reviews)
Loved my stay here, it has been renovated and the room was perfect with a big shower, comfy bed and a nice kitchen. The beach is right next door and restaurants, market, shopping in walking distance. The trolley to downtown is across the street and free, just give the driver a tip :) The property has a great outdoor courtyard area for lounging. I enjoyed staying at this quaint 1950's style property that is part of other smaller original properties versus the big high rises that have take over the area. I plan to stay here next time I visit Siesta Key!

Reviewed on Oct 13, 2025

Where to stay in Whitfield Estates

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

While visiting South Sarasota, you might make a stop by sights like The Landings and Coconuts Family Entertainment Center.

Find hotels in South Sarasota

Whitfield Estates Hotel Deals

Lantern Inn & Suites

Lantern Inn & Suites

2.5 out of 5
7251 N Tamiami Trl, Sarasota, FL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Oct 20 to Oct 21
$85 total
Oct 20 - Oct 21
Total with taxes and fees
9/10 Wonderful! (1,189 reviews)
"La habitacion estaba excelente limpia."

Reviewed on Oct 5, 2025

Lantern Inn & Suites
Ramada by Wyndham Sarasota Waterfront

Ramada by Wyndham Sarasota Waterfront

3 out of 5
7150 N Tamiami Trail, Sarasota, FL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $123 total per night from Oct 16 to Oct 17
$123 total
Oct 16 - Oct 17
Total with taxes and fees
7.6/10 Good! (1,006 reviews)
"Breakfast room and reception staff - VERY good"

Reviewed on Oct 10, 2025

Ramada by Wyndham Sarasota Waterfront
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $81 total per night from Oct 16 to Oct 17
$81 total
Oct 16 - Oct 17
Total with taxes and fees
9/10 Wonderful! (4,440 reviews)
"Beautiful hotel especially for the price."

Reviewed on Oct 9, 2025

Kompose Boutique Hotel
See all 13,650 properties in Whitfield 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 Whitfield Estates

Lido Beach showing general coastal views and a sandy beach

Lido Beach

Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.

Lido Beach
Mall at University Town Center

Mall at University Town Center

You can search for that perfect souvenir at Mall at University Town Center during your visit to Sarasota. Attend a sporting event or discover the beautiful sunsets in this family-friendly area.

Mall at University Town Center
St. Armands Circle featuring a statue or sculpture

St. Armands Circle

Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.

St. Armands Circle

Things to do

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$55
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
74% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

$99
per adult
Anna Maria Island & Bradenton Beach Parasailing Tour
See all activities in Sarasota
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.