Popular hotels
Insights
Cheapest hotels
Where to stay

Vacation rentals in Siesta Key

Search and compare Siesta Key, FL vacation rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customize your results by hotel chain, amenities, price, and more.

Search for hotels as many times as you want – for free.

Show Map

Refine Your Search

Star ratings
Guest Ratings
Amenities
Freebies
See all filters

Popular holiday rental in Siesta Key

Enter your travel dates to find the best prices.

Sort by

Popular
PriceStarsReview ScoreDistance
Filter by star ratings
All filters
Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village
Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village

Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village

Siesta Key, FL, United States
A sunny Siesta Key adventure is made even better for those who book a stay in beautiful Beach Road. This welcoming 2-bed, 2-bath home away from home offers up enough space to accommodate 6 guests at a time making it an ideal property for a group of friends or a family getaway. Beach Road enjoys a prime location directly across the street from Siesta Key Beach and is only mere blocks from exciting stops like Siesta Key Village. Whether you're looking to cozy up or head out and enjoy the best of local shopping, dining, and nightlife, Beach Road puts you in the heart of the fun.
Air Conditioning
Free Wi-Fi
9.3
Excellent
32 reviews
Location
1.0 km from city centre
C$ 389
View Deal
All 2,687 vacation rentals in Siesta Key

Travel insights for vacation rentals in Siesta Key

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Siesta Key.

What is the cheapest month to book a vacation rental in Siesta Key?

The cheapest month to book a vacation rental in Siesta Key is October (C$ 194). Conversely, the most expensive month to stay in Siesta Key is May (C$ 1,354).

How far ahead should you book a vacation rental in Siesta Key?

Save money by booking a vacation rental at least 86 days before your trip to Siesta Key. The lowest price found when booking 86 days ahead was C$ 328 per night.

Find deals

Cheapest vacation rentals in Siesta Key, Florida

Currently, these are the lowest-priced vacation rentals in Siesta Key we've come across for the dates selected. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
Siesta Heron Suites & Villas
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Key, FL, United States
4.8 km from city centre
Air Conditioning
C$ 204
Avg. per night
View Deal
Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key
Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key

Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key

Siesta Key, FL, United States
4.8 km from city centre
Air Conditioning
Free Wi-Fi
C$ 214
Avg. per night
View Deal
Updated unit with easy beach access on Siesta Key
Updated unit with easy beach access on Siesta Key

Updated unit with easy beach access on Siesta Key

Siesta Key, FL, United States
2.7 km from city centre
Air Conditioning
Free Wi-Fi
C$ 236
Avg. per night
View Deal
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Siesta Key, FL, United States
2.6 km from city centre
Air Conditioning
Free Wi-Fi
C$ 244
Avg. per night
View Deal
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Siesta Key, FL, United States
1.0 km from city centre
Air Conditioning
Free Wi-Fi
C$ 250
Avg. per night
View Deal
The Ringling Beach House
The Ringling Beach House

The Ringling Beach House

Siesta Key, FL, United States
1.4 km from city centre
Air Conditioning
C$ 271
Avg. per night
View Deal
Siesta Key Palms
Siesta Key Palms

Siesta Key Palms

1017 Point Of Rocks Road, Siesta Key, FL, United States
2.6 km from city centre
Free Wi-Fi
Parking
C$ 291
Avg. per night
View Deal
Tropical Beach Cottage-Steps to the Beach-Short Walk to Siesta Key Village
Tropical Beach Cottage-Steps to the Beach-Short Walk to Siesta Key Village

Tropical Beach Cottage-Steps to the Beach-Short Walk to Siesta Key Village

Siesta Key, FL, United States
2.2 km from city centre
Air Conditioning
C$ 291
Avg. per night
View Deal
Siesta Key Beachside Villas
Siesta Key Beachside Villas

Siesta Key Beachside Villas

Siesta Key, FL, United States
2.3 km from city centre
Air Conditioning
C$ 294
Avg. per night
View Deal
Villa 41 - Premium Plus
Villa 41 - Premium Plus

Villa 41 - Premium Plus

Siesta Key, FL, United States
0.9 km from city centre
Air Conditioning
C$ 317
Avg. per night
View Deal
Fully Renovated Beachside Getaway With Heated Pool Walk to Restaurants
Fully Renovated Beachside Getaway With Heated Pool Walk to Restaurants

Fully Renovated Beachside Getaway With Heated Pool Walk to Restaurants

Siesta Key, FL, United States
2.6 km from city centre
Air Conditioning
Free Wi-Fi
C$ 343
Avg. per night
View Deal

Other accommodations in Siesta Key

Turtle Beach Resort
Turtle Beach Resort

Turtle Beach Resort

9049 Midnight Pass Road, Siesta Key, FL, United States
6.4 km from city centre
Free Wi-Fi
Parking
C$ 330
Avg. per night
View Deal
Seaspray Resort
Seaspray Resort

Seaspray Resort

574 Canal Road, Siesta Key, FL, United States
1.3 km from city centre
Free Wi-Fi
Air Conditioning
C$ 310
Avg. per night
View Deal
Cottages at Siesta Key Inn
Cottages at Siesta Key Inn

Cottages at Siesta Key Inn

1105 Point of Rocks Road, Siesta Key, FL, United States
2.6 km from city centre
Free Wi-Fi
Parking
C$ 215
Avg. per night
View Deal

Where to stay in Siesta Key

Scroll through the map to find vacation rentals close to the Siesta Key neighborhood(s) you plan on visiting. As an added benefit, users can click a vacation rental they're interesting in to find helpful information and deals for that vacation rental.

Facts about staying in Siesta Key

  • How much does a vacation rental in Siesta Key cost?

    Siesta Key vacation rentals are C$ 547/night on average. However, you may find that prices fluctuate depending on the time of year. For example, May is the most expensive month to book a vacation rental in Siesta Key, and October is often the cheapest month to book. Recently, our users found rentals for C$ 194/night - which is currently the cheapest price. Keep in mind that anything C$ 509/night or less is still considered a good deal.

  • What’s the closest vacation rental to Sarasota Bradenton Intl Airport?

    It’s only 16.6 km from Sarasota Bradenton Intl Airport to Bianco Sands by Beachside Management (the nearest Siesta Key vacation rental to the airport).

  • Are there any Resort vacation rentals in Siesta Key?

    Yes, there are 11 Resort vacation rentals in Siesta Key. According to our data, Captiva Beach Resort is currently the most popular Resort rental in the city.

Find better results for your stay in Siesta Key