Siesta Key Vacation Rentals - HomeToGo base64Hash Siesta Key Vacation Rentals - HomeToGo

Siesta Key Vacation Rentals

Find 7,691 available home rentals from 34 partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Bed and breakfast

  • Distance to center

    • 2 km
    • 5 km
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • Air conditioning
    • Parking
    • Kitchen
    • Washing machine
    • TV
    • Balcony/patio
    • Dishwasher
    • Microwave
    • Jacuzzi
    • Yard
    • Crib
    • Sauna
    • Fireplace
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Siesta Key

Find your perfect vacation rental in Siesta Key from just $130 per night!

House Siesta Key
House ∙ 14 guests ∙ 5 bedrooms

520 m² House

Siesta Key, Sarasota County, Florida, United States
This spacious house rental in Bay Isle features a private heated pool, jacuzzi, and a family-friendly yard, perfect for 14 guests.
from $1,087
per night
Outstanding(161 ratings)
from $1,087
per night
View deal
House Siesta Key
House ∙ 7 guests ∙ 3 bedrooms

172 m² House

Siesta Key, Sarasota County, Florida, United States
This Siesta Key house rental offers beach access, a kitchen, and a balcony, perfect for family getaways with pets.
from $524
per night
Outstanding(4 ratings)
from $524
per night
View deal
Condo Siesta Key
Condo ∙ 6 guests ∙ 3 bedrooms

139 m² Condo

Siesta Key, Sarasota County, Florida, United States
This Siesta Key condo features a pool and parking, accommodating up to six guests for a perfect beach getaway.
from $396
per night
Excellent(18 ratings)
from $396
per night
View deal
Condo Siesta Key
Condo ∙ 6 guests ∙ 2 bedrooms

Condo

Siesta Key, Sarasota County, Florida, United States
This waterfront condo in Siesta Key features a heated pool, kitchen, and parking, perfect for up to six guests seeking fun.
from $152
per night
Outstanding(20 ratings)
from $152
per night
View deal
House Siesta Key
House ∙ 8 guests ∙ 3 bedrooms

107 m² House

Siesta Key, Sarasota County, Florida, United States
This Siesta Key house rental offers waterfront access, a kitchen, and a balcony for families and pets, accommodating up to 8 guests.
from $759
per night
Outstanding(188 ratings)
from $759
per night
View deal
House Siesta Key
House ∙ 8 guests ∙ 3 bedrooms

104 m² House

Siesta Key, Sarasota County, Florida, United States
This Sarasota house rental features a kitchen, yard, and parking, perfect for a fun getaway with up to 8 guests.
from $384
per night
from $384
per night
View deal
Condo Siesta Key
Condo ∙ 6 guests ∙ 2 bedrooms

93 m² Condo

Siesta Key, Sarasota County, Florida, United States
This Siesta Key condo offers beach access, a private heated pool, and family-friendly amenities for an unforgettable getaway.
from $398
per night
Outstanding(57 ratings)
from $398
per night
View deal
House Siesta Key
House ∙ 5 guests ∙ 2 bedrooms

158 m² House

Siesta Key, Sarasota County, Florida, United States
This South Sarasota house rental features a kitchen, yard, parking, and welcomes pets, perfect for a family getaway.
from $238
per night
Outstanding(228 ratings)
from $238
per night
View deal
Castle Siesta Key
Castle ∙ 12 guests ∙ 5 bedrooms

279 m² Castle

Siesta Key, Sarasota County, Florida, United States
This Siesta Key castle rental features a private heated pool, jacuzzi, and family-friendly amenities, perfect for 12 guests.
from $933
per night
Very good(118 ratings)
from $933
per night
View deal
Cabin Siesta Key
Cabin ∙ 8 guests ∙ 4 bedrooms

120 m² Cabin

Siesta Key, Sarasota County, Florida, United States
This waterfront cottage in Siesta Key features a private heated pool, kitchen, yard, and parking, perfect for up to 8 guests.
from $565
per night
Outstanding(44 ratings)
from $565
per night
View deal
House Siesta Key
House ∙ 12 guests ∙ 4 bedrooms

214 m² House

Siesta Key, Sarasota County, Florida, United States
This waterfront house rental in Siesta Key features a private heated pool, jacuzzi, and a spacious yard for the whole family.
from $518
per night
Outstanding(20 ratings)
from $518
per night
View deal
House Siesta Key
House ∙ 10 guests ∙ 5 bedrooms

158 m² House

Siesta Key, Sarasota County, Florida, United States
This Siesta Key house rental features a private heated pool, jacuzzi, and a yard, perfect for up to 10 guests to unwind.
from $1,053
per night
Outstanding(12 ratings)
from $1,053
per night
View deal
House Siesta Key
House ∙ 4 guests ∙ 2 bedrooms

House

Siesta Key, Sarasota County, Florida, United States
This Siesta Key house rental for four features beach access, a kitchen, pet-friendly policies, and convenient parking.
from $353
per night
Very good(64 ratings)
from $353
per night
View deal
House Siesta Key
House ∙ 8 guests ∙ 4 bedrooms

198 m² House

Siesta Key, Sarasota County, Florida, United States
This Siesta Key house rental offers beach access, a pool, a kitchen, a balcony, and parking for up to 8 guests.
from $1,151
per night
Outstanding(11 ratings)
from $1,151
per night
View deal
House Siesta Key
House ∙ 8 guests ∙ 4 bedrooms

258 m² House

Siesta Key, Sarasota County, Florida, United States
This waterfront house rental in Sarasota features a private heated pool, jacuzzi, and a kitchen perfect for family getaways.
from $791
per night
Outstanding(30 ratings)
from $791
per night
View deal

Vacation rentals and apartments with air conditioning

House Siesta Key
from $1,303 per night
House ∙ 10 guests ∙ 7 bedrooms

429 m² House

5.0
Outstanding(64 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
Condo Siesta Key
from $835 per night
Condo ∙ 8 guests ∙ 4 bedrooms

256 m² Condo

5.0
Outstanding(87 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
House Siesta Key
from $410 per night
House ∙ 28 guests ∙ 8 bedrooms

House

4.9
Outstanding(148 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
See all offers

Apartments with a balcony or patio

Villa Siesta Key
from $227 per night
Villa ∙ 5 guests ∙ 2 bedrooms

151 m² Villa

4.6
Excellent(111 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House Siesta Key
from $376 per night
House ∙ 8 guests ∙ 4 bedrooms

House

Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House Siesta Key
from $379 per night
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

4.9
Outstanding(156 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

House Siesta Key
from $156 per night
House ∙ 5 guests ∙ 3 bedrooms

121 m² House

Siesta Key, Sarasota County, Florida, United States
Yard
View deal
Apartment Siesta Key
from $627 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

121 m² Apartment

4.9
Outstanding(50 ratings)
Siesta Key, Sarasota County, Florida, United States
Yard
View deal
House Siesta Key
from $567 per night
House ∙ 8 guests ∙ 3 bedrooms

168 m² House

4.9
Outstanding(108 ratings)
Siesta Key, Sarasota County, Florida, United States
Yard
View deal
See all offers

Budget-friendly Rentals in Siesta Key

Find Fantastic yet Inexpensive Rentals

House Siesta Key
from $305 per night
House ∙ 4 guests ∙ 2 bedrooms

167 m² House

5.0
Outstanding(77 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $164 per night
Condo ∙ 4 guests ∙ 2 bedrooms

100 m² Condo

4.5
Excellent(19 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Apartment Siesta Key
from $193 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

94 m² Apartment

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Top-Rated Offers and Accommodations in Siesta Key

Book Vacation Rentals with the Highest User Rating

Condo Siesta Key
from $339 per night
Condo ∙ 6 guests ∙ 2 bedrooms

165 m² Condo

5.0
Outstanding(192 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $316 per night
House ∙ 8 guests ∙ 3 bedrooms

186 m² House

4.8
Outstanding(50 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $441 per night
House ∙ 10 guests ∙ 4 bedrooms

173 m² House

4.9
Outstanding(47 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Siesta Key

How are reviews collected?
Margaret H.
Guest verified by HomeToGo

Was absolutely amazing beautiful property everything you could want or need in a vacation rental home. Was very satisfied.

Reviewed on 11/2/2025 | Family
House Siesta Key
from $563 per night
House ∙ 9 guests ∙ 3 bedrooms
4.5
Excellent(2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Kerri B.
Guest verified by HomeToGo

Everything was perfect; location, cleanliness, large place... The condo sat right on Midnight Pass Rd with easy access to the beach. The back patio faces straight down to intercoastal. There was covered parking. The condo itself was a lot bigger than I expected. Everything was decorated beautifully. The rainfall showerheads were lovely. It was so clean and stocked with many extra items. The two pools were saltwater, one being right out the back patio. It was very quiet inside the condo.

Reviewed on 8/2/2025 | Family
Condo Siesta Key
from $292 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(4 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Ashley G.
Guest verified by HomeToGo

We loved everything about this house! Very well appointed, comfortable beds, clean, and excellent location! We are already planning our next trip.:)

Reviewed on 7/27/2025 | Family
House Siesta Key
from $931 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(114 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Michele J.
Guest verified by HomeToGo

The home was beautiful. I think the management company needs to evaluate the staff that they have working on the property.

Reviewed on 6/23/2025 | Family
House Siesta Key
from $1,041 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(99 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
ANDREW T.
Guest verified by HomeToGo

The condo location is excellent! The amenities of the condo association (pool, tennis, and pickleball courts, and secure parking), were excellent, the condo unit itself was a bit dated, but clean and well appointed. WiFI was fast and tv offerings from Netflix, Prime Video, Hulu, Paramount , were nice to be able to watch in the evening after a day at the beach or lounging at the pool.

Reviewed on 4/1/2025 | Family
Condo Siesta Key
from $318 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.5
Excellent(47 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Vanessa Y.
Guest verified by HomeToGo

We enjoyed our stay at Avanti Villa 534. The property is exactly like the pictures and was clean. Not a bad walk to the beach or village. We incurred no problems with any features of the property and communication was great with the host. They even left a delicious treat on arrival, and some nice starter necessities such as cleaning and bathing products! They also offered us another nights stay, but unfortunately we couldn’t take advantage of it ! We had a wonderful stay, just wish it could have been longer! One thing I will say, and it has nothing to do with the property, but bring bug spray when you come, the no-see-ums are brutal!

Reviewed on 7/2/2024 | Family
House Siesta Key
from $586 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding(9 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Michael G.
Guest verified by HomeToGo

Home was very nice and was as represented. Service was responsive and excellent.

Reviewed on 7/2/2024 | Family
House Siesta Key
from $1,204 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(59 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Pete M.
Guest verified by HomeToGo

Just a few things missing: facial tissues, hand soap in bathrooms, bed pillows that were too high to be comfortable. The towels provided by service were sometimes gross, sometimes ok, Most frustrating was the tv in living room. Only being able to watch on Youtube tv made us miss several of our morning news shows. Had to watch the NFL Sunday night game outside by the pool, bundled in blankets. Overall, very good vacationtime there. Too bad the weather was so cold.

Reviewed on 1/29/2024 | Couple
House Siesta Key
from $801 per night
House ∙ 12 guests ∙ 3 bedrooms
4.9
Outstanding(51 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Amy S.
Guest verified by HomeToGo

Endless Views was a perfect spot for our vacation to Siesta Key. Roomy, clean, and with the added plus on an elevator for our luggage and handicapped son. A short walk to both the village and the beach. We enjoyed every minute!

Reviewed on 3/13/2023 | Family
House Siesta Key
from $604 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(21 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Siesta Key

  • Pool (5,863)
  • WiFi (7,357)
  • Air conditioning (7,160)
  • Parking (617)
  • Kitchen (7,379)
  • Washing machine (5,509)
  • TV (7,159)
  • Pet-friendly (1,557)
  • Balcony/patio (2,306)
  • Dishwasher (5,468)
  • Microwave (6,006)
  • Grill (5,058)

More than two-thirds of the vacation rentals provide a pool, which makes Siesta Key a fantastic vacation destination for people looking to spend vacation poolside. Interestingly, HomeToGo's data shows that more condo provide a pool than apartment rental. Additionally, they can host 5 people, on average, while apartment rental with pools can welcome an average of 6 guests. If you would also like to be close to the water, one-third of the vacation homes offering a pool are located within 2 kilometres of the waterfront.

Price and Availability Index in Siesta Key

Click on any bar to see price and availability information

Vacation Rental Price Information in Siesta Key

The graph shows average prices of rentals in Siesta Key for the next twelve months. Prices reach a peak a week in March. The price per night in a vacation rental in Siesta Key this week (3/21 – 3/28) costs on average $790. The cheapest week to book a vacation rental is in May (5/9 – 5/16).

Rental availability information in Siesta Key

The graph shows the weekly availability rate in Siesta Keyfor the next twelve months. So far, the week with the least available vacation rentals in Siesta Key is in November (11/21 – 11/28). On the contrary, you will find the highest number of available vacation rentals in a week of October (10/17 – 10/24).

Have a relaxing Vacation in a Siesta Key rental

Siesta Key is an island off the coast of Sarasota, Florida. Siesta Key vacation home rentals are typically modern and spacious with everything your family needs for a great vacation. The properties are located on the coast within walking distance of the beaches. Treat your family to a property with a sea view or a private pool.

What are the best activities for families in Siesta Key?

Explore Siesta Key with the Kids

Mote Marine Laboratory and Aquarium is a great place to take the kids for a day out. Here they can view marine wildlife including manatees and otters and many spieces of fish. There's also an outdoor shark tank. The aquarium is an interesting and educational experience where the whole family can learn about the different marine species local to the region.

Kids will also love playing and swimming on Turtle Beach which is a beautiful white sandy beach. If you're lucky. you might even catch a glimpse of dolphins or manatees. There's also a small park with a play area for kids, boat launch, and fishing piers as well as a picnic area.

Where are the unique attractions in Siesta Key?

Visit the Beautiful Beaches of the Area

Crescent Beach is considered one of the best beaches in the area. It's long and sandy and is a great place to swim or walk. Alternatively, head to Coquina Beach which is also a great place for swimming, life guards are on watch on this popular beach.

Information about vacation rentals in Siesta Key

🏡 Vacation rentals available 7,279 rentals
🌙 Nightly prices starting at $130
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 1,378 homes
🏊 Vacation rentals with pools 5,658 homes
13 reviews
Siesta Key vacation rentals have an average rating of 4.7/5 on 13 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Siesta Key?

We found 7,279 vacation homes in Siesta Key available for your next trip.

What are the most popular vacation home amenities in Siesta Key?

Many travellers are searching for Pool, Internet, and Air conditioning when booking a vacation home in Siesta Key.

Are there pet-friendly vacation rentals in Siesta Key?

If you're travelling with a dog, over 19% of vacation rentals in Siesta Key are pet-friendly.

What's the best month to visit Siesta Key?

If you're looking for balmy weather, August and June are typically the hottest months in Siesta Key with temperatures around 33 °C. February and January in Siesta Key are the coldest, with 13 °C on average.

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