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Siesta Key Monthly Rentals

Siesta Key
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Siesta Key
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Monthly Rentals with pools

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Pet-Friendly Monthly Rentals

Monthly Rentals with patio

Monthly Rentals with patio

Monthly Rentals with internet

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Top-rated monthly rentals in Siesta Key

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House Siesta Key
$6,174 for 28 nights
House ∙ 8 guests ∙ 3 bedrooms

House in Sarasota with Grill, Pool & Yard

4.7
Excellent (206 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$9,285 for 28 nights
House ∙ 24 guests ∙ 8 bedrooms

House in Sarasota with Private Parking

4.9
Outstanding (137 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$20,001 for 28 nights
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Siesta Key with Yard, Grill & Pool

5.0
Outstanding (119 ratings)
Siesta Key, Sarasota County, Florida, United States
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Best Deals and Discounts on Monthly Rentals

Save up to 17%

Condo Siesta Key
-17%
$6,170
$5,135 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool & Grill

4.2
Very good (56 ratings)
Siesta Key, Sarasota County, Florida, United States
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Monthly Rentals in Siesta Key: Top Accommodations

Condo Siesta Key
$8,781 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Grill & Pool

4.9
Outstanding (69 ratings)
Siesta Key, Sarasota County, Florida, United States
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Apartment Siesta Key
$3,579 for 28 nights
Apartment ∙ 2 guests ∙ 1 bedroom

Lovely Rental Apartment in Siesta Key

4.5
Excellent (33 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$5,285 for 28 nights
House ∙ 4 guests ∙ 2 bedrooms

Beautiful Vacation Home in Siesta Key

4.4
Very good (51 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$8,400 for 28 nights
House ∙ 7 guests ∙ 2 bedrooms

House in Siesta Key with Pool + Next to Beach

4.0
Very good (6 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$17,664 for 28 nights
House ∙ 12 guests ∙ 4 bedrooms

Lovely House in Siesta Key + Spectacular Views + Beach Nearby

4.6
Excellent (10 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$11,200 for 28 nights
Condo ∙ 8 guests ∙ 2 bedrooms

Condo in Sarasota with Patio, Pool & Grill + Gulf View

5.0
Outstanding (45 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$7,000 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Patio & Pool

4.6
Excellent (67 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$10,500 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Grill, Pool & Sauna + Multiple Views

4.6
Excellent (44 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$5,922 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Pool & Grill

4.7
Excellent (16 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

Condo Siesta Key
$8,522 for 28 nights
Condo ∙ 4 guests ∙ 2 bedrooms

Nice Condo in Lido Key with Patio

4.8
Outstanding (60 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$6,860 for 28 nights
House ∙ 5 guests ∙ 3 bedrooms

House in Siesta Key with Grill, Yard & Patio

5.0
Outstanding (7 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$12,386 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Beautiful Condo in Siesta Key with Pool

4.4
Very good (6 ratings)
Siesta Key, Sarasota County, Florida, United States
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Stay Cool: Monthly Rentals with Air Conditioning

Condo  Siesta Key
$14,560 for 28 nights
Condo ∙ 8 guests ∙ 4 bedrooms

Pleasant Condo in Siesta Key with Over-Sized Garage + Gulf Views

5.0
Outstanding (76 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Condo  Siesta Key
$2,800 for 28 nights
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Siesta Key with Sauna & Pool

4.6
Excellent (40 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Condo  Siesta Key
$6,190 for 28 nights
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Siesta Key with Sauna, Grill & Patio

5.0
Outstanding (3 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Stay connected: Monthly Rentals with internet

Condo  Siesta Key
$7,473 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Interior Parking + Beach Nearby

4.5
Excellent (66 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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Condo  Siesta Key
$10,787 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool & Grill + Gulf View

4.7
Excellent (12 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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House  Siesta Key
$8,521 for 28 nights
House ∙ 10 guests ∙ 3 bedrooms

Vacation Home in Gulf Gate Estates with Private Pool

4.8
Outstanding (25 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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Soak Up the Sun: Monthly Rentals with Patios

House  Siesta Key
$12,333 for 28 nights
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Siesta Key + Gulf Views

4.5
Excellent (2 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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House  Siesta Key
$6,435 for 28 nights
House ∙ 6 guests ∙ 3 bedrooms

Nice Vacation Home in Ridge Wood Heights with Electric Pool

5.0
Outstanding (96 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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Condo  Siesta Key
$5,562 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool, Sauna & Patio

Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

House Siesta Key
$14,649 for 28 nights
House ∙ 9 guests ∙ 3 bedrooms

Vacation Home in Siesta Key with Private Garage + Canal Views

Siesta Key, Sarasota County, Florida, United States
Free cancellation
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Condo Siesta Key
$7,560 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Pool, Hot Tub

4.7
Excellent (13 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$11,011 for 28 nights
House ∙ 10 guests ∙ 3 bedrooms

Charming House in Siesta Key with Wood-Burning Fireplace

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
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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! November is the most affortable time to stay in Siesta Key with a big group, when nightly prices for Monthly Rentals will range from $336 to $621 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 $711 per day for a family of 8 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 November with prices starting at $100 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.
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Information about Siesta Key Monthly Rentals

📏 Average home size 107 m²
😎 Least busy month September
🛏️ Popular home types Condo and House rental
🌡️ Hottest months August and June
❄️ Coldest months 55 °F in February and January
🌧️ Rainiest months 18 rainy days in August and July

Frequently Asked Questions

Siesta Key Monthly Rentals: How much does a stay cost?

You can get an incredible rental for somewhere between $336 and $621 and find discounts up to 66%!

Siesta Key Monthly Rentals: does HomeToGo offer a wide variety of vacation homes for large groups?

Usually the size of a Condo is 107 m² and can fit 5 guests on average which is great for medium-sized groups and families.

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

There are more than 6,779 homes to rent in Siesta Key. The best time to find availability for longer stays is in September when home rentals have high availability.

Siesta Key Monthly Rentals: what types of vacation homes are available in Siesta Key?

We would suggest choosing from our incredible selection of Condos and House rentals in Siesta Key.

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

Rates for a longer stay in vacation rental in Siesta Key start from $100 per night, but many hosts offer discounts for stays of 14 days or longer.

Can you book mid-term rentals in Siesta Key feature a pool?

Definitely, over 78% of accommodations in Siesta Key offer a pool.

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