A marina with numerous boats docked, a bridge in the background, and a cityscape with high-rise buildings.

Rosemary District Vacations from $644

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Rosemary District Vacation

Let our Rosemary District vacation packages take you to a destination where unforgettable memories are waiting to be made. While it's especially renowned for its cafes, there's plenty more to love about this neighborhood. Want to head out and see the sights during your trip to Rosemary District? Pencil in a visit to nearby attractions like St. Armands Circle, Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens. No matter what your ideal Rosemary District vacation may look like, you can turn it into reality with Expedia.

The Latest Rosemary District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A swimming pool with lounge chairs and a fire feature.
    Jan 31 - Feb 5

    voco Sarasota by IHG + Flight

    Central Sarasota
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,002 reviews)
    Roundtrip • Islip (ISP) - Tampa (TPA)
    ISP - TPA • 1 stop TPA - ISP • 1 stop
    $1,038
    $644
    per traveler
    found 1 day ago
    voco Sarasota by IHG
  • A modern kitchen with a large island, white cabinetry, and a view of the beach.
    Jan 10 - Jan 15

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,324 reviews)
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,076
    $651
    per traveler
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • A modern living room with a large window, a sofa set, a coffee table, and a dining area.
    Jan 26 - Jan 31

    CW Resort + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (304 reviews)
    "Brand new facility. Very comfy beds, TONS of space, and breakfast better and cheaper than anything else in the area. Ate there every morning."
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,482
    $903
    per traveler
    found 1 day ago
    CW Resort
  • A bedroom with a large bed, a nightstand, a chair, and a view of the ocean.
    Jan 28 - Feb 3

    Crystal Palms Beach Resort + Flight

    Sunshine Beach
    6 nights
    3.5 star property
    8.8/10 - Excellent (2,416 reviews)
    "It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,207
    $751
    per traveler
    found 1 day ago
    Crystal Palms Beach Resort
  • A spacious living room with a large beige sectional sofa, a fireplace, a ceiling fan, and a dining area with a table and chairs.
    Jan 26 - Jan 31

    Pescador Pool and Spa Home + Flight

    Seminole
    5 nights
    3.0 star property
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,563
    $978
    per traveler
    found 1 day ago
    Pescador Pool and Spa Home

Where to stay in Rosemary District

Find the best Rosemary District areas and neighborhoods for the activities you enjoy most.
A beach lifeguard tower with a flag, a rescue sign, and people walking on the sand.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

A cityscape with a mix of modern and historic buildings, palm trees, and a cloudy sky.

South Sarasota

Though South Sarasota might not have many top sights, you can venture to the surrounding area to see attractions like Siesta Key Beach and The Landings.

A theater with a sign reading "Florida Studio Theatre" and a smaller sign for "Wednesday's Child Now Playing".

Central Sarasota

Beaches, exotic gardens and a museum for a famous circus are located in the city’s central sector. Visit an upscale shopping area on an island of its own.

A large metallic sculpture in a public square with a brick-paved walkway, surrounded by trees and buildings.

Downtown Sarasota

If you're spending some time in Downtown Sarasota, Sarasota Opera House and Regal Hollywood - Sarasota are top sights worth seeing.

A river with a fountain, surrounded by lush greenery and palm trees, with buildings in the background.

Palmer Ranch

When in Palmer Ranch, you can plan a visit to Stoneybrook Golf & Country Club and Turtle Beach, some noteworthy sights in the nearby area.

Discover the most popular places to visit in Rosemary District

Van Wezel Performing Arts Hall

8.4/10 (109 reviews)
See a diverse range of exciting musical, dance and comedy shows at this architectural landmark inspired by the jagged shape of seashells.
See properties

What to do near Rosemary District

Mangroves, Manatees & a Hidden Beach Kayak Tour (Siesta Key)

Mangrove Tunnel & Manatee Kayak Eco-Tour

$59
per adult
96% of travelers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
See all activities near Rosemary District

Rosemary District Hotel Deals

An outdoor patio area with multiple seating arrangements, including sofas and chairs, and ceiling fans.

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel
4.0 star property
Rosemary District
8.2 out of 10, Very good, (589 reviews)
$204 nightly
The price is $230
Nov 29 - Nov 30
Total with taxes and fees
The Sarasota Modern, a Tribute Portfolio Hotel
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.
See all properties in Rosemary District
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.