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Holiday homes in Siesta Key You’ll Love

Top-Rated Siesta Key Holiday homes for Every Budget and Style!

Looking for a holiday home in Siesta Key (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Siesta Key.

We found 700 Holiday-homes in Siesta Key and the surrounding area (within 20 miles)

Oceanfront home with heated pool in Sarasota, USA

Oceanfront home with heated pool

Villa in Sarasota near Siesta Key, Florida , 8648 Dunmore Drive
Providing a garden, Oceanfront home with heated pool features accommodations in Sarasota.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $70.00 Show details »

Sarasota Villa with Pool Access about 4 Mi to Beach! in Sarasota, USA

Sarasota Villa with Pool Access about 4...

Villa in Sarasota near Siesta Key, Florida
Sarasota Villa with Pool Access about 4 Mi to Beach! is located in Sarasota, just 11 miles from Venice Theatre and 12 miles from St Armands Circle.
  • Parking
  • Fitness centre

Exceptional 4 Reviews 9.5

from $211.31 Show details »

LUX VILLAs on beautiful Palmer Ranch in Vamo, USA

LUX VILLAs on beautiful Palmer Ranch

Villa in Vamo near Siesta Key, Florida , 3635 White Pine Court
13 miles from The John and Mable Ringling Museum of Art in Vamo, LUX VILLAs on beautiful Palmer Ranch features accommodations with access to a hot tub...
  • Parking
  • Restaurant
  • Pets allowed
  • Fitness centre
  • Family rooms

Fabulous 38 Reviews 8.6

from $316.73 Show details »

Lanai and Community Pool Access Sarasota Oasis! in Sarasota, USA

Lanai and Community Pool Access Sarasota...

Villa in Sarasota near Siesta Key, Florida
Lanai and Community Pool Access Sarasota Oasis! is located in Sarasota, just 9.1 miles from Sarasota Opera and 9.2 miles from Marina Jack Restaurant a...
  • Parking

Exceptional 2 Reviews 10.0

from $204.53 Show details »

Crescent Beach Villas in Siesta Key, USA

Crescent Beach Villas

Villa in Siesta Key, Florida , 1126 Crescent Street
Crescent Beach Villas enjoys a location in Siesta Key, a 3-minute walk from Crescent Beach and one mile from Turtle Beach.
  • Parking

Very good 25 Reviews 8.2

from $339.09 Show details »

Sun and Sea in Siesta Key, USA

Sun and Sea

Villa in Siesta Key, Florida , 1135 Sun N Sea Drive Unit 1 & 2
Sun and Sea offers accommodations in Siesta Key, a 2-minute walk from Crescent Beach and 1.3 miles from Turtle Beach.
  • Parking

Fabulous 26 Reviews 8.8

from $526.78 Show details »

Boutique Chic Villa. Steps From Pool, Pier, & Beach. Find Your Vacation Here. in Siesta Key, USA

Boutique Chic Villa. Steps From Pool, Pi...

Villa in Siesta Key, Florida , 1272 Moonmist Circle
Featuring a garden, Boutique Chic Villa.
  • Parking

Good 2 Reviews 7.5

from $226.31 Show details »

Discover the beauty of Siesta Key at Siesta Villa Whispering Palms in Siesta Key, USA

Discover the beauty of Siesta Key at Sie...

Villa in Siesta Key, Florida , 1331 Moonmist Drive
Discover the beauty of Siesta Key at Siesta Villa Whispering Palms is located in Siesta Key, just 11 miles from The John and Mable Ringling Museum of ...
  • Parking

no reviews

from $83.00 Show details »

Siesta Villa Coralline - Charming Beach Villa on Siesta Key in Sarasota, USA

Siesta Villa Coralline - Charming Beach...

Villa in Sarasota near Siesta Key, Florida , 1143 North Moonmist Court
Siesta Villa Coralline - Charming Beach Villa on Siesta Key is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 7...
  • Parking

Exceptional 1 Reviews 10.0

from $223.00 Show details »

Derby Bay View in Siesta Key, USA

Derby Bay View

Villa in Siesta Key, Florida , 1232 Derby Lane
Derby Bay View is a recently renovated villa in Siesta Key where guests can take a dip in the outdoor swimming pool and make the most of the free Wifi...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 68 Reviews 8.3

from $392.05 Show details »

Beautiful property on Siesta Key in Siesta Key, USA

Beautiful property on Siesta Key

Villa in Siesta Key, Florida , 1234 Derby Lane
Just a 5-minute walk from Crescent Beach and one mile from Siesta Key Beach, Beautiful property on Siesta Key features accommodations in Siesta Key wi...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 58 Reviews 7.9

from $338.00 Show details »

Sea Club II in Siesta Key, USA

Sea Club II

Villa in Siesta Key, Florida , 5955 Midnight Pass Road
Sea Club II offers accommodations in Siesta Key, a 6-minute walk from Crescent Beach and 0.9 miles from Siesta Key Beach.
  • Parking

Passable 23 Reviews 5.5

from $257.89 Show details »

Lakefront Getaway in Sunny Florida with Heated Pool in Sarasota, USA

Lakefront Getaway in Sunny Florida with...

Villa in Sarasota near Siesta Key, Florida , 3711 Meridale Road
Lakefront Getaway in Sunny Florida with Heated Pool is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 7.9 miles...
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Exceptional 3 Reviews 10.0

from $377.53 Show details »

Sarasota Resort-Like Living Near Siesta Key For 10 in Sarasota, USA

Sarasota Resort-Like Living Near Siesta...

Villa in Sarasota near Siesta Key, Florida , 6007 Beneva Rd
Sarasota Resort-Like Living Near Siesta Key For 10 is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 7.5 miles ...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 2 Reviews 7.0

from $311.25 Show details »

Happy Dolphin Siesta Key in Siesta Key, USA

Happy Dolphin Siesta Key

Villa in Siesta Key, Florida , 5584 Shadow Lawn Drive
Just a 12-minute walk from Siesta Key Beach and 0.7 miles from Crescent Beach, Happy Dolphin Siesta Key features accommodations in Siesta Key, with an...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $100.00 Show details »

5min from the beach 8 min from Siesta Key in Sarasota, USA

5min from the beach 8 min from Siesta Ke...

Villa in Sarasota near Siesta Key, Florida , 5744 South Beneva Road
5min from the beach 8 min from Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.3 miles fro...
  • Parking
  • Family rooms

Superb 21 Reviews 9.2

from $237.59 Show details »

Siesta Key Beach Resort and Suites in Sarasota, USA

Siesta Key Beach Resort and Suites

Villa in Sarasota near Siesta Key, Florida , 5311 Ocean Boulevard
Located just 1 minutes’ walk from the beach, this Siesta Key resort features a swimming pool.
  • Parking
  • Restaurant
  • Bar
  • Family rooms
  • Outdoor pool

Fabulous 535 Reviews 8.8

from $270.97 Show details »

Siesta Key Beachside Villas in Sarasota, USA

Siesta Key Beachside Villas

Villa in Sarasota near Siesta Key, Florida , 124 Columbus BLVD
Siesta Key Beachside Villas is located in the heart of Siesta Key.
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming pool

Fabulous 348 Reviews 8.9

from $248.43 Show details »

Siesta Key Waterfront Estate W Pool Privacy! in Sarasota, USA

Siesta Key Waterfront Estate W Pool Priv...

Villa in Sarasota near Siesta Key, Florida , 4765 Riverwood Circle
Siesta Key Waterfront Estate W Pool Privacy! is a recently renovated villa in Sarasota where guests can make the most of the fitness center and garden...
  • Parking
  • Fitness centre
  • Family rooms
  • Outdoor pool
  • Swimming pool

Exceptional 3 Reviews 10.0

from $1.112.82 Show details »

Cozy retreat in sunny Florida in Sarasota, USA

Cozy retreat in sunny Florida

Villa in Sarasota near Siesta Key, Florida , 4624 Flatbush Avenue
Cozy retreat in sunny Florida offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.7 miles from Sarasota O...
  • Parking

Exceptional 2 Reviews 9.5

from $198.47 Show details »

Tranquil Court Oasis in Sarasota, USA

Tranquil Court Oasis

Villa in Sarasota near Siesta Key, Florida , 4490 Riverwood Avenue
Providing a garden, Tranquil Court Oasis offers accommodations in Sarasota.
  • Parking
  • Family rooms
  • Outdoor pool
  • Kids' outdoor play equipment
  • Swimming Pool

Exceptional 5 Reviews 10.0

from $56.00 Show details »

Sunshine Home /Siesta Key/Vacation Home in Sarasota, USA

Sunshine Home /Siesta Key/Vacation Home

Villa in Sarasota near Siesta Key, Florida , 4009 Winthrop Street
Sunshine Home /Siesta Key/Vacation Home is located in Sarasota, just 6.5 miles from Marina Jack Restaurant and Marina and 7.4 miles from Sarasota Coun...
  • Parking

no reviews

from $63.00 Show details »

House on Hibiscus: #SiestaBeach in Sarasota, USA

House on Hibiscus: #SiestaBeach

Villa in Sarasota near Siesta Key, Florida , 2060 Hibiscus Street
Offering a garden, House on Hibiscus: #SiestaBeach provides accommodations in Sarasota.
  • Parking
  • Family rooms

Exceptional 1 Reviews 10.0

from $80.00 Show details »

Sarasota Golf View in Sarasota, USA

Sarasota Golf View

Villa in Sarasota near Siesta Key, Florida , 3227 Pine Valley Drive
Offering a garden, Sarasota Golf View offers accommodations in Sarasota.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $100.00 Show details »

Mid -Century Modern Villa in SRQ -Starfish 641 in Sarasota, USA

Mid -Century Modern Villa in SRQ -Starfi...

Villa in Sarasota near Siesta Key, Florida , 641 North Jefferson Avenue
Mid -Century Modern Villa in SRQ -Starfish 641 offers accommodations in Sarasota, 5 miles from The John and Mable Ringling Museum of Art and 1.8 miles...
  • Parking
  • Swimming Pool

Exceptional 9 Reviews 10.0

from $98.00 Show details »

Number of Holiday homes in Siesta Key 700
Number of guest ratings 3,798
Average price per night $416.00
Lowest price per night $50,00
Highest price per night $6.060,98

Top 10 Most Popular Holiday-homes in Siesta Key

Explore the Most Popular Holiday-homes in Siesta Key – Ranked by Average Guest Ratings.

Top 10 Cheapest Holiday-homes in Siesta Key

Discover the Cheapest Holiday-homes in Siesta Key – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Siesta Key

Check out the Most Booked Holiday-homes in Siesta Key – Based on Guest Popularity.

Holiday homes in Siesta Key (Florida), comfortable and familiar

Staying in a holiday or vacation home in Siesta Key can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Siesta Key for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Siesta Key should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com