Vacations in Siesta Key

Vacations in Siesta Key

2 travellers

KAYAK searches hundreds of travel sites at once for vacation package deals in Siesta Key

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Search
Best Deals
Tips
Vacation information

Cheap Siesta Key package deals

Discover the best prices by selecting your travel dates on KAYAK.
Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

C$ 647 - C$ 2,141C$ 2,141 - C$ 3,634C$ 3,634 - C$ 5,128C$ 5,128 - C$ 6,622C$ 6,622+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Siesta Key flight and hotel deals

Show all
Summer Salt - Siesta Key
Summer Salt - Siesta Key
Summer Salt
10 Wonderful
Parking
Free Wi-Fi
Pool
Pet friendly
Pittsburgh
Meals not included
3 nights + flight
C$ 1,499
Turtle Beach Resort - Siesta Key - Pool
Turtle Beach Resort - Siesta Key - Pool
Turtle Beach Resort
9 Wonderful
Parking
Free Wi-Fi
Pool
Pet friendly
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 873
Sunset Splash - Siesta Key
Sunset Splash - Siesta Key
Sunset Splash
10 Wonderful
Parking
Free Wi-Fi
Pool
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 5,317
Captiva Beach Resort - Siesta Key - Patio
Captiva Beach Resort - Siesta Key - Patio
Captiva Beach Resort
9 Wonderful
Parking
Free Wi-Fi
Pool
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 684
Palm Bay Club 8th Floor On Complex Private Beach - Siesta Key - Dining room
Palm Bay Club 8th Floor On Complex Private Beach - Siesta Key - Dining room
Palm Bay Club 8th Floor On Complex Private Beach
Free Wi-Fi
Pittsburgh
Meals not included
3 nights + flight
C$ 1,691
Siesta Key Island Rentals - Siesta Key - Pool
Siesta Key Island Rentals - Siesta Key - Pool
Siesta Key Island Rentals
8.5 Very good
Parking
Pool
Raleigh-Durham
Meals not included
3 nights + flight
C$ 646
Siesta Key Beachside Villas - Siesta Key - Patio
Siesta Key Beachside Villas - Siesta Key - Patio
Siesta Key Beachside Villas
8.7 Very good
Free Wi-Fi
Pool
Pet friendly
Pittsburgh
Meals not included
3 nights + flight
C$ 956
Siesta Palooza - Siesta Key
Siesta Palooza - Siesta Key
Siesta Palooza
Parking
Free Wi-Fi
Pool
Pet friendly
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 4,610
The Ringling Beach House - Siesta Key - Balcony
The Ringling Beach House - Siesta Key - Balcony
The Ringling Beach House
8.2 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 962
Beach Club Modern Condo C Building - Siesta Key - Beach
Beach Club Modern Condo C Building - Siesta Key - Beach
Beach Club Modern Condo C Building
9.1 Wonderful
Free Wi-Fi
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 1,270
Sugar Sand Cottage - Siesta Key - Living room
Sugar Sand Cottage - Siesta Key - Living room
Sugar Sand Cottage
Parking
Free Wi-Fi
Pool
Pet friendly
Pittsburgh
Meals not included
3 nights + flight
C$ 5,129
Island House - Siesta Key
Island House - Siesta Key
Island House
8.3 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Hartford Bradley Intl
Meals not included
3 nights + flight
C$ 3,879
Siesta Palms By The Beach - Siesta Key
Siesta Palms By The Beach - Siesta Key
Siesta Palms By The Beach
9 Wonderful
Parking
Free Wi-Fi
Pool
Pittsburgh
Meals not included
3 nights + flight
C$ 828
Lulu's Key House Kemp Ridley 1/1 Downstairs - Siesta Key - Beach
Lulu's Key House Kemp Ridley 1/1 Downstairs - Siesta Key - Beach
Lulu's Key House Kemp Ridley 1/1 Downstairs
9.5 Wonderful
Free Wi-Fi
Pittsburgh
Meals not included
3 nights + flight
C$ 1,039
Siesta Key Inn - Siesta Key
Siesta Key Inn - Siesta Key
Siesta Key Inn
7.9 Good
Parking
Free Wi-Fi
Pool
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 983
Family Apartment with Pool in siesta key florida - Siesta Key
Family Apartment with Pool in siesta key florida - Siesta Key
Family Apartment with Pool in siesta key florida
Pool
Pittsburgh
Meals not included
3 nights + flight
C$ 3,525

Last minute vacation packages to Siesta Key

Show all
Gulf side, spacious 1 bedroom, 1 bath, 200 steps to Crescent Beach - Siesta Key
Gulf side, spacious 1 bedroom, 1 bath, 200 steps to Crescent Beach - Siesta Key
Gulf side, spacious 1 bedroom, 1 bath, 200 steps to Crescent Beach
8.8 Very good
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 1,699

When to book a vacation in Siesta Key

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding Siesta Key package deals

  • There are loads of types of vacations in Siesta Key and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top vacation C$ 887; Family vacation C$ 887.

Where to stay in Siesta Key

Our map will help you find the perfect place to stay for your vacation in Siesta Key by showing you the exact location of each hotel.

Everything you need to know for your vacation in Siesta Key

Siesta Key vacation information

Top vacation (Flight+Hotel)C$ 887
Family vacation (Flight+Hotel)C$ 887

Siesta Key vacation: Search Siesta Key vacation packages on KAYAK. KAYAK is a travel tool that searches Siesta Key trips on hundreds of travel sites to help you find the Siesta Key package that suits you best. Discover Siesta Key deals now and book your Siesta Key flight and hotel today.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.