Siesta Key Monthly Rentals

Siesta Key

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$100 - $199

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Monthly Rentals with pools

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Monthly Rentals with patio

Monthly Rentals with internet

Top-rated monthly rentals in Siesta Key

Browse our top rated monthly rentals offers

Jul 13 - Jul 20

$665 for 7 nights

Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Gulf Gate Estates

4.6

Excellent (121 ratings)

Siesta Key, Sarasota County, Florida, United States

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Sep 30 - Oct 7

-62%

$3,489

$1,326 for 7 nights

House ∙ 24 guests ∙ 8 bedrooms

House in Sarasota with Private Parking

4.9

Outstanding (117 ratings)

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

-64%

$3,635

$1,293 for 7 nights

House ∙ 8 guests ∙ 3 bedrooms

House in Siesta Key with Ample Parking

4.5

Excellent (34 ratings)

Siesta Key, Sarasota County, Florida, United States

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Best Deals and Discounts on Monthly Rentals

Save up to 56%

Sep 14 - Sep 21

-41%

$2,177

$1,295 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool & Grill

4.0

Very good (4 ratings)

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

-34%

$1,813

$1,193 for 7 nights

House ∙ 4 guests ∙ 2 bedrooms

Beautiful Vacation Home in Siesta Key

4.6

Excellent (28 ratings)

Siesta Key, Sarasota County, Florida, United States

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Sep 29 - Oct 6

-56%

$1,763

$775 for 7 nights

Cottage ∙ 4 guests ∙ 1 bedroom

Lovely Cottage in Siesta Key with Grill + Close to Beach

4.0

Very good (31 ratings)

Siesta Key, Sarasota County, Florida, United States

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Monthly Rentals in Siesta Key: Top Accommodations

Dec 2 - Dec 9

$1,433 for 7 nights

Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment in Lido Key with Grill

4.7

Excellent (66 ratings)

Siesta Key, Sarasota County, Florida, United States

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Aug 3 - Aug 10

-22%

$1,575

$1,225 for 7 nights

Condo ∙ 4 guests ∙ 2 bedrooms

Beautiful Condo in Siesta Key with Pool + Next to Beach

4.7

Excellent (47 ratings)

Siesta Key, Sarasota County, Florida, United States

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Oct 28 - Nov 4

-78%

$4,585

$995 for 7 nights

House ∙ 6 guests ∙ 2 bedrooms

House in Siesta Key with Overnight Parking

4.8

Outstanding (5 ratings)

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

-43%

$2,450

$1,406 for 7 nights

Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Siesta Key with Grill & Pool

5.0

Outstanding (34 ratings)

Siesta Key, Sarasota County, Florida, United States

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Oct 28 - Nov 4

-74%

$7,029

$1,820 for 7 nights

House ∙ 9 guests ∙ 3 bedrooms

Vacation Home in Siesta Key with Private Balcony

4.8

Outstanding (19 ratings)

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

-18%

$1,845

$1,522 for 7 nights

Condo ∙ 6 guests ∙ 3 bedrooms

Wonderful Condo in Siesta Key with Grill & Pool + Next to Beach

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

-30%

$4,998

$3,500 for 7 nights

House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Siesta Key with Spacious Patio

5.0

Outstanding (165 ratings)

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

$1,198 for 7 nights

House ∙ 4 guests ∙ 1 bedroom

Wonderful House in Siesta Key with Yard + Next to Beach

4.6

Excellent (24 ratings)

Siesta Key, Sarasota County, Florida, United States

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Dec 2 - Dec 9

-67%

$2,693

$898 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Grill & Pool + Pool Views

4.7

Excellent (66 ratings)

Siesta Key, Sarasota County, Florida, United States

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Budget-friendly monthly rentals in Siesta Key

Our top value vacation rentals for monthly rentals

Sep 30 - Oct 7

-33%

$1,412

$945 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Outdoor Pool

4.5

Excellent

Siesta Key, Sarasota County, Florida, United States

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Sep 29 - Oct 6

-58%

$1,945

$823 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Family Friendly Beautiful Condo in Siesta Key with Screened-In Balcony

4.7

Excellent (70 ratings)

Siesta Key, Sarasota County, Florida, United States

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Sep 14 - Sep 21

-49%

$3,133

$1,609 for 7 nights

Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Siesta Key with Large Pool + Spectacular View

4.9

Outstanding (37 ratings)

Siesta Key, Sarasota County, Florida, United States

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Stay Cool: Monthly Rentals with Air Conditioning

May 18 - May 25

-27%

$945

$693 for 7 nights

House ∙ 3 guests ∙ 1 bedroom

Beautiful Vacation Home in Siesta Key with Grill

4.9

Outstanding (78 ratings)

Siesta Key, Sarasota County, Florida, United States

Air conditioning

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Dec 1 - Dec 8

-45%

$1,600

$876 for 7 nights

Condo ∙ 4 guests ∙ 1 bedroom

Condo in Siesta Key with Grill

4.8

Outstanding (78 ratings)

Siesta Key, Sarasota County, Florida, United States

Air conditioning

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Dec 2 - Dec 9

$1,393 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Grill & Pool

4.9

Outstanding (147 ratings)

Siesta Key, Sarasota County, Florida, United States

Air conditioning

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Stay Connected: Monthly Rentals with Internet

Sep 30 - Oct 7

-35%

$3,080

$1,995 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Pool & Grill + Great Views

5.0

Outstanding (104 ratings)

Siesta Key, Sarasota County, Florida, United States

Internet

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Sep 30 - Oct 7

-20%

$4,375

$3,492 for 7 nights

House ∙ 12 guests ∙ 4 bedrooms

House in Siesta Key with Grill

Siesta Key, Sarasota County, Florida, United States

Internet

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Dec 16 - Dec 23

$2,400 for 7 nights

Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool, Yard & Grill + Degree View

5.0

Outstanding (96 ratings)

Siesta Key, Sarasota County, Florida, United States

Internet

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Soak Up the Sun: Monthly Rentals with Patios

Sep 29 - Oct 6

-22%

$812

$630 for 7 nights

Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool & Grill

4.5

Excellent (60 ratings)

Siesta Key, Sarasota County, Florida, United States

Balcony/Patio

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Oct 4 - Oct 11

-61%

$2,303

$907 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Wonderful Condo in Sarasota with Grill & Pool + Next to Beach

4.6

Excellent (98 ratings)

Siesta Key, Sarasota County, Florida, United States

Balcony/Patio

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Dec 10 - Dec 17

-61%

$2,303

$903 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Pool & Grill + Beach Nearby

4.7

Excellent (93 ratings)

Siesta Key, Sarasota County, Florida, United States

Balcony/Patio

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Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

May 4 - May 11

$5,328 for 7 nights

Condo ∙ 4 guests ∙ 2 bedrooms

Wonderful Condo in Siesta Key with Spacious Patio + Amazing Views

Siesta Key, Sarasota County, Florida, United States

Free cancellation

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Sep 3 - Sep 10

-27%

$3,823

$2,800 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Outdoor Whirlpool

5.0

Outstanding (69 ratings)

Siesta Key, Sarasota County, Florida, United States

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Sep 30 - Oct 7

-64%

$5,593

$1,995 for 7 nights

House ∙ 6 guests ∙ 3 bedrooms

House in Bay Isle with Jetted Whirlpool

4.8

Outstanding (57 ratings)

Siesta Key, Sarasota County, Florida, United States

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Monthly Rentals in Siesta Key for Any Type of Traveler

Looking to accommodate a large group in Siesta Key?

Begin browsing our top Monthly Rentals for big groups and plan the perfect getaway! September is the most affortable time to stay in Siesta Key with a big group, when nightly prices for Monthly Rentals will range from $307 to $674 per night. Book wonderful Monthly Rentals for large groups in Siesta Key, complete with private pool, big kitchen, and plenty of space to enjoy. HomeToGo offers numerous Monthly Rentals in Siesta Key with seven or more bedrooms and seven or more bathrooms.

Trying to plan a big family vacation in Siesta Key?

Many Monthly Rentals in Siesta Key will cost around $495 per day for a family of 5 people but there are many affordable options in Siesta Key to choose from. Lots of Monthly Rentals in Siesta Key come with family-friendly features, including hot tubs, private pool, TV, games, and many others. Siesta Key has tons of exciting family-friendly activities to do, including swimming, hiking, biking, and many other outdoor activities. Search HomeToGo's selection of large Monthly Rentals in Siesta Key, able to bed a big family with seven or more rooms and several washrooms. Start your search for family-friendly Monthly Rentals now!

Looking for a romantic vacation in Siesta Key with your partner?

Search HomeToGo's best Monthly Rentals for romantic getaways in Siesta Key today! The most affordable time to book is September with prices starting at $94 per night. There are lots of fun activities to do with your partner on your couples trip, including swimming, hiking, biking, and many other outdoor activities. Reserve amazing Monthly Rentals in Siesta Key for a private retreat, complete with jacuzzi, sauna, and a amazing view of Siesta Key's surrounding scenery.

Information about Siesta Key Monthly Rentals

😎 Least busy month	November
🥳 Busiest month	February
🛏️ Popular home types	House rental and Apartment rental
🌡️ Hottest months	91 °F in August and June
❄️ Coldest months	February and January
🌧️ Rainiest months	August and July

Frequently Asked Questions

How many vacation rentals in Siesta Key are available for a long stay?

You can find more than 5,262 homes to rent in Siesta Key. The best time to find availability for longer stays is in November when home rentals have high availability.

What types of vacation homes can I find for Siesta Key Monthly Rentals?

There are many Apartment rental and House rental that are great for Siesta Key Monthly Rentals.

Siesta Key Monthly Rentals: How much does it cost to rent a vacation home in Siesta Key?

The average cost for a vacation rental in Siesta Key is usually between $307 and $674 per night.

Can I find a vacation home for a group of guests for Siesta Key Monthly Rentals?

The size of a House rental is 178 m² and may fit 7 people on average which is ideal for large groups.

How much does a mid-term vacation home rental in Siesta Key cost?

Cost of a longer stay in vacation rental in Siesta Key range from $94 per night, but many hosts can offer discounts for stays of 14 days or longer.

How many monthly vacation home rentals in Siesta Key have a pool?

Absolutely, over 78% of accommodations in Siesta Key come with a pool.

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