Holiday homes and accommodation in Siesta Key - HomeToGo base64Hash Holiday homes and accommodation in Siesta Key - HomeToGo

Holiday homes and accommodation in Siesta Key

Find 7,358 available offers from 35 partners
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Top 15 Recommended holiday lettings in Siesta Key

Find your perfect holiday home, apartment or cottage in Siesta Key from just £120 per night!

House Siesta Key
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with terrace, garden & barbecue

Siesta Key, Sarasota County, Florida, United States
from £646
per night
Outstanding(10 ratings)
from £646
per night
View deal
House Siesta Key
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly big holiday home with garden, private pool & barbeque | Pet-friendly

Siesta Key, Sarasota County, Florida, United States
from £263
per night
Outstanding(33 ratings)
from £263
per night
View deal
Condo Siesta Key
Condo ∙ 8 guests ∙ 3 bedrooms

Child-friendly condo with heated pool, sauna & barbeque | Close to the beach

Siesta Key, Sarasota County, Florida, United States
from £346
per night
Outstanding(49 ratings)
from £346
per night
View deal
House Siesta Key
House ∙ 11 guests ∙ 5 bedrooms

Family-friendly house with terrace, hot tub & private pool | City view | Close to the beach | Dogs allowed

Siesta Key, Sarasota County, Florida, United States
from £359
per night
Outstanding(1 rating)
from £359
per night
View deal
House Siesta Key
House ∙ 10 guests ∙ 5 bedrooms

House with garden, private pool & barbeque | Suitable for remote work

Siesta Key, Sarasota County, Florida, United States
from £352
per night
Outstanding(130 ratings)
from £352
per night
View deal
House Siesta Key
House ∙ 4 guests ∙ 2 bedrooms

House with hot tub, private pool & barbecue | Nature view

Siesta Key, Sarasota County, Florida, United States
from £152
per night
Outstanding(77 ratings)
from £152
per night
View deal
House Siesta Key
House ∙ 14 guests ∙ 5 bedrooms

Family-oriented spacious holiday home with jacuzzi, garden & BBQ | Close to the beach | Perfect for remote work

Siesta Key, Sarasota County, Florida, United States
from £396
per night
Outstanding(151 ratings)
from £396
per night
View deal
House Siesta Key
House ∙ 9 guests ∙ 3 bedrooms

Fully equipped holiday home with heated pool, terrace & barbecue | Nature view | Beach nearby

Siesta Key, Sarasota County, Florida, United States
from £316
per night
Excellent(55 ratings)
from £316
per night
View deal
House Siesta Key
House ∙ 11 guests ∙ 4 bedrooms

Holiday home with private pool, terrace & barbeque | Nature view

Siesta Key, Sarasota County, Florida, United States
from £311
per night
Excellent(113 ratings)
from £311
per night
View deal
House Siesta Key
House ∙ 10 guests ∙ 5 bedrooms

Holiday home with garden, BBQ & terrace | Perfect for remote work

Siesta Key, Sarasota County, Florida, United States
from £691
per night
Outstanding(121 ratings)
from £691
per night
View deal
Condo Siesta Key
Condo ∙ 8 guests ∙ 3 bedrooms

Family-friendly charming condo with barbeque, jacuzzi & heated pool | Close to the beach

Siesta Key, Sarasota County, Florida, United States
from £246
per night
from £246
per night
View deal
House Siesta Key
House ∙ 8 guests ∙ 4 bedrooms

House with BBQ, private pool & terrace | Perfect for remote work

Siesta Key, Sarasota County, Florida, United States
from £169
per night
from £169
per night
View deal
House Siesta Key
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped ample house with terrace, private pool & BBQ | Close to the beach

Siesta Key, Sarasota County, Florida, United States
from £596
per night
Very good(9 ratings)
from £596
per night
View deal
House Siesta Key
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, garden & barbeque

Siesta Key, Sarasota County, Florida, United States
from £183
per night
Outstanding(1 rating)
from £183
per night
View deal
House Siesta Key
House ∙ 14 guests ∙ 5 bedrooms

House with barbecue & pool

Siesta Key, Sarasota County, Florida, United States
from £849
per night
Outstanding(18 ratings)
from £849
per night
View deal

Holiday lettings and apartments with air conditioning

House  Siesta Key
from £306 per night
House ∙ 9 guests ∙ 3 bedrooms

Fully equipped house with heated pool, barbecue & terrace | Nature view | Next to the beach

4.3
Very good(26 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
House  Siesta Key
from £293 per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, garden & barbeque | City view

5.0
Outstanding(81 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
House  Siesta Key
from £304 per night
House ∙ 8 guests ∙ 5 bedrooms

Child-friendly holiday home with hot tub, barbecue & garden | Suitable for remote work | Pets allowed

5.0
Outstanding(24 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
See all offers

Best holiday homes with a patio or terrace

Villa  Siesta Key
from £300 per night
Villa ∙ 8 guests ∙ 2 bedrooms

Villa with BBQ, heated pool & terrace

4.8
Outstanding(7 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House  Siesta Key
from £178 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with terrace | City view | Perfect for remote work

4.9
Outstanding(141 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House  Siesta Key
from £355 per night
House ∙ 12 guests ∙ 4 bedrooms

Holiday home with private pool, terrace & garden

4.7
Excellent(63 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
See all offers

Holiday homes and cottages with a garden

Cottage  Siesta Key
from £192 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Fully equipped charming cottage with terrace, garden & BBQ | Pets allowed

4.9
Outstanding(32 ratings)
Siesta Key, Sarasota County, Florida, United States
Garden
View deal
House  Siesta Key
from £360 per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly ample house with terrace, private pool & barbeque | Perfect for remote work | Dogs allowed

5.0
Outstanding(94 ratings)
Siesta Key, Sarasota County, Florida, United States
Garden
View deal
House  Siesta Key
from £130 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful holiday home with garden & private pool | Pets allowed

4.6
Excellent(30 ratings)
Siesta Key, Sarasota County, Florida, United States
Garden
View deal
See all offers

Budget-friendly Holiday Homes in Siesta Key

Find Fantastic yet Cheap Lettings

Condo Siesta Key
from £401 per night
Condo ∙ 8 guests ∙ 4 bedrooms

Child-friendly pleasant flat with terrace, barbeque & heated pool | City view | Next to the beach | Pets allowed

5.0
Outstanding(85 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from £248 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly house with terrace, BBQ & garden | Good for workation | Pets allowed

4.0
Very good(15 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from £133 per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with sauna, heated pool & barbeque | Nature view

5.0
Outstanding(38 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Top-Rated Lettings and Properties in Siesta Key

Book Holiday Letting Offers with the Highest User Rating

House Siesta Key
from £336 per night
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped wonderful holiday home with private pool & terrace | City view | Good for workation

4.5
Excellent(66 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from £268 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with barbecue, private pool & terrace | Nature view

4.9
Outstanding(59 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from £298 per night
House ∙ 8 guests ∙ 3 bedrooms

House with barbecue & terrace

4.6
Excellent(39 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
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 23/06/2025 | Family
House Siesta Key
from £418 per night
HomeToGo
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(82 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Laura m.
Guest verified by HomeToGo

The pictures do not do this unit justice. It is beautiful and very roomy. One of the pools is right next to the unit. The “toy closet” has many many beach chairs, several beach umbrellas, floats, beach toys, a basketball and football, a cooler, a fishing rod (no hooks or fishing supplies, but it’s there to use, and a beach wagon. It made our stay so nice. The master bathroom is absolutely beautiful. The kitchen was really well stocked with any cooking tool, pot, pan, or casserole you could want. And a full drawer of spices. We did cook on the grill one day. The grill is right by the pool.

Reviewed on 20/06/2025 | Family
Condo Siesta Key
from £163 per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(3 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 01/04/2025 | Family
Condo Siesta Key
from £156 per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.5
Excellent(58 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 02/07/2024 | Family
House Siesta Key
from £232 per night
HomeToGo
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding(5 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 02/07/2024 | Family
House Siesta Key
from £520 per night
HomeToGo
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(50 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 29/01/2024 | Couple
House Siesta Key
from £352 per night
HomeToGo
House ∙ 12 guests ∙ 3 bedrooms
5.0
Outstanding(44 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 13/03/2023 | Family
House Siesta Key
from £230 per night
HomeToGo
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(21 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
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Trust in the quality and comfort of your stay with verified guest reviews.

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Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

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Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

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

Popular holiday rental amenities in Siesta Key

  • Pool (5,711)
  • WiFi (6,900)
  • Air conditioning (6,852)
  • Parking (579)
  • TV (6,823)
  • Washing machine (5,357)
  • Balcony/patio (2,159)
  • Grill (4,800)
  • Dishwasher (5,054)
  • Kitchen (6,966)
  • No smoking (6,462)
  • Microwave (5,603)

More than two-thirds of the holiday lettings offer a pool, which makes Siesta Key an excellent destination for travellers looking to spend their holidays poolside. Additionally, more condo have pools than any other accommodation type. They are an excellent choice if you go in a group of 5, as that is the number of people they can welcome on average. If you would also like to be near the water, one-third of the holiday lettings with a pool are situated within 2 kilometres of the waterfront.

Price and Availability Index for Siesta Key

Click on any bar to see price and availability information

Holiday Letting Price Information in Siesta Key

In the above graph, you will find information on the average prices of holiday lettings in Siesta Key. Prices reach their highest point in April, when prices are an average of £409 a night (04/04 – 11/04). Prices are at their lowest during one week in September (06/09 – 13/09), when costs are £315 on average.

Rental availability information in Siesta Key

Check how busy Siesta Key is with our availability graph. In February (07/02 – 14/02), only 23 are available. The week with the highest percentage of available lettings is in September (27/09 – 04/10).

Siesta Key vacation rentals: the perfect beach holiday in an island paradise

Not far from Sarasota, and just next to the enticing Gulf of Mexico, sits the eight mile long Siesta Key. It’s been named America’s Best Beach, and once you get here, it’s easy to see why. Its four main beaches are best known for their white sand, pure blue waters, and lots of sports activities.

A family-friendly location, the region is ideal for those with children, however Siesta Key also offers the perfect romantic setting for couples. Dinner while bathed in moonlight at a waterfront oyster bar? Breakfast from your beach terrace in your Siesta Key holiday home? With any Siesta Key holiday letting you choose, you’ll have direct access to the bay and beach — just footsteps away. Around the shore are many dining options and plenty of activities to choose from. Restaurants range from budget to luxurious; the beaches here some of the most coveted in the country. In short, Siesta Key is an island paradise.

What are the best activities for families in Siesta Key?

Where to go with children in Siesta Key

Got kids? After a morning sleeping in at your Siesta Key holiday home, go check out the Crowley Museum & Nature Centre, where you can enjoy hiking around nature trails, visit the wildlife sanctuary, and overlook the Myakka River. Another interesting place for kids near to your Siesta Key holiday letting is the Florida Gulf Coast Railroad Museum, open most weekends. At the Mote Marine Laboratory and Science Centre, both young and old can enjoy learning about marine life. Visit their giant aquariums and see sharks, eels or manatees up close. If your young ones ever want to experience circus life, they can learn all about it at the Circus Museum.

Whether you choose to lounge around on the beach all day, work on your tan, or take up a more active holiday activities around Siesta Key Beach, you’ll have a great time. Your Siesta Key holiday home has all the amenities you need to make this holiday perfect.

What are the top sights in Siesta Key?

The beaches of Siesta Key

Water sport lovers will have a blast in Siesta Key; it’s the ultimate beach destination. Its four main areas are: Siesta Beach, Crescent Beach, Turtle Beach and Siesta Key Village. When staying in your Siesta Key holiday letting , try visiting each one, as they all have a unique charm.

The most popular, Siesta Beach, was in fact rated the number one beach in the United States in 2011. Here, you can lounge on its lovely quartz sand, enjoying the cool feeling under your toes. Try some active sports in the tennis and volleyball courts, or go with your family for a picnic. For catching the gorgeous sunset, head to Crescent Beach, known for its fine white sands. With its stunning blue waters and peaceful vibe, it’s also a great place for a romantic date with your favourites person.

You’ll find Turtle Beach on Siesta Key’s southern tip. It's notably darker sand has more shells, so if you love collecting, or have little ones who do, head there. There are also playgrounds and sports areas on the sand, which is likely to be not close to your Siesta Beach holiday letting .

Siesta Village is where you’ll get to see wildlife like parrots and various shore birds. Don’t forget your camera if you enjoy nature photography. You may just spy a beautiful snowy egret, an ibis or a stork. Those who love the underwater thrill of snorkeling can head out to Point of Rocks. It’s an area lauded as the best spot on Florida’s west coast for snorkeling.

What are the must-see attractions in Siesta Key?

Discover paradise at Siesta Key

Point of Rocks

Forming a natural boundary at Crescent Beach's south end, Point-of-Rocks is great for snorkelling and shallow-water bathing. Children will especially enjoy discovering the marine life.

Turtle Beach

Named after the turtles who nest here, Turtle Beach is perfect for family picnics and taking in picturesque sunsets. Collect shells, swim, sunbathe or fish here.

Siesta Farmers Market

This market has it all from fruit, vegetables and olive oil, to paintings, vintage photos, shell artwork, ceramics and beauty products. After bargain hunting, relax with a coffee and enjoy the live music.

Siesta Beach

White-powdered sand, turquoise waters and gentle breezes define the tropical paradise that is Siesta Beach. This award-winning beach is unbeatable for blissful atmosphere, even offering the chance to spot dolphins.

Crescent Beach

This southern portion of Siesta Beach has won the accolade of having "the whitest and finest sand in the world". Paddleboarding, kayaking and snorkelling are popular activities here.

Information about holiday rentals in Siesta Key

🏡 Holiday homes available 7,358 rentals
🌙 Nightly prices from £120
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly rentals 1,574 properties
🏊 Holiday rentals with pools 5,733 properties
10 reviews
Siesta Key holiday rentals have an average rating of 4.6/5 across 10 reviews left by travellers.

Frequently Asked Questions

What is the nightly price for a holiday home in Siesta Key?

The average starting price for a holiday cottage or rental in Siesta Key is £120 per night. Prices vary depending on the type of holiday let, season, and amenities. Use HomeToGo to compare deals and find the best value for your trip.

How many holiday homes are available to book in Siesta Key? And what are the most popular types of holiday lets?

There are 7,358 holiday homes from 33 different providers on offer in Siesta Key. The most popular types of holiday lets in Siesta Key include condos and house rentals. They’re ideal whether you’re planning a romantic escape or a group getaway. HomeToGo makes it easy to find a holiday home that fits your needs.

What is the most searched holiday apartment amenity in Siesta Key?

When choosing a holiday apartment in Siesta Key, consider looking for a place with Pool, Internet, or Air conditioning, which are the three most popular amenities for this destination.

Do you offer holiday homes with a swimming pool in Siesta Key?

Looking for a pool? You’ll find that one-third of holiday cottages and homes in Siesta Key have one. Whether you’re travelling with kids or just want a splash, you’re sorted with 5,733 options available. Use the 'pool' filter on HomeToGo to see your options.

What is the best time of year to travel to Siesta Key?

August and June are the best months for sun lovers in Siesta Key.

Can you get deals on holiday rentals in Siesta Key?

You can find fabulous discounts on holiday homes in Siesta Key with the nightly price of a letting beginning at £120 - and HomeToGo has introduced plenty of features that make it easy to uncover some awesome offers. If you don't have set dates for your break, you can use HomeToGo's flexible dates technology to easily look for great value time periods and get discounts of up to 10%. Additionally, HomeToGo's 'distance from' filter lets you uncover hidden treasure holiday rentals in great value, under-the-radar locales that are just as close to the area of your choice, whether that's a beach, lake, ski region or city centre. Start your search as soon as possible to make the most of a wide range of offers and the best deals - and do so without worries by selecting HomeToGo's 'free cancellation' filter when you search.

What are the pros of finding a holiday rental in Siesta Key with HomeToGo?

From increased privacy away from the crowds to more space to enjoy with your family, friends or partner, holiday lettings in Siesta Key provide a variety of benefits. HomeToGo surfaces genuine ratings written by previous guests, and searching is safe, simple, and stress-free - so with 7,358 rentals from 33 providers in the area, you're sure to discover the perfect holiday home with the amenities and features you need in Siesta Key.

Do you offer holiday accommodation for couples in Siesta Key?

Absolutely – couples love the range of holiday lettings available in Siesta Key. Think cosy cottages or stylish apartments for a peaceful escape. Find your perfect base with HomeToGo.

Can I book a waterfront holiday rental in Siesta Key?

You can book one of 7318 waterfront holiday homes in Siesta Key for a truly scenic break. They're great for beach lovers or anyone seeking a peaceful retreat by the water. Use HomeToGo’s "Near the water" filter to find your perfect waterfront holiday let.

Why should I book my holiday rental with HomeToGo?

With HomeToGo, you get access to the world’s largest selection of holiday lettings – all in one place. We compare prices across providers to help you save time and money. Discover your ideal holiday home with ease on HomeToGo.

Can I find family-friendly holiday lettings in Siesta Key?

Holiday cottages in Siesta Key are a great fit for families, offering comfort, space and handy amenities. Many come with space for medium-sized groups and families and practical features like kitchens and gardens. Use HomeToGo to explore family-friendly holiday cottages with ease.

Can I cancel my holiday rental booking for free?

Worried about changes? Plenty of holiday rentals listed on HomeToGo come with free cancellation options. Just make sure to check the property's policy before booking.

Is it possible to rent a holiday home for a weekend getaway in Siesta Key?

Yes, weekend breaks are easy to plan with flexible holiday rentals in Siesta Key. Many homes offer short stays without long commitments. HomeToGo helps you spot the best weekend-friendly options fast.

Are there any last-minute holiday rental deals in Siesta Key?

Need a quick break? Last-minute holiday is just a few clicks away in Siesta Key. You might even save up to 10% if you’re flexible with dates. Use HomeToGo’s filters to see what’s available right now.

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