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Siesta Key Monthly Rentals

Siesta Key
Anytime
Guests
Siesta Key
Anytime
Guests

Choose from a fantastic selection of monthly rentals

Price per night
Up to $100
$100 - $199
From $200
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
Bedrooms
Any
1 bedroom
2+ bedrooms
Show all 6,351 properties

Popular amenities for Siesta Key Monthly Rentals

Find the perfect home for your stay

Monthly Rentals with pools

Monthly Rentals with pools

Pet-Friendly Monthly Rentals

Pet-Friendly Monthly Rentals

Monthly Rentals with patio

Monthly Rentals with patio

Monthly Rentals with internet

Monthly Rentals with internet

Top-rated monthly rentals in Siesta Key

Browse our top rated monthly rentals offers

Condo Siesta Key
$8,064 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Grill, Patio & Pool

4.9
Outstanding (148 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$7,252 for 28 nights
House ∙ 4 guests ∙ 2 bedrooms

Beautiful Vacation Home in Siesta Key

4.6
Excellent (43 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$11,603 for 28 nights
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home in Sarasota with Free Parking

5.0
Outstanding (31 ratings)
Siesta Key, Sarasota County, Florida, United States
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Best Deals and Discounts on Monthly Rentals

Save up to 56%

Apartment Siesta Key
Jul 1 - Jul 29
-23%
$5,572
$4,275 for 28 nights
Apartment ∙ 2 guests ∙ 1 bedroom

Lovely Rental Apartment in Siesta Key

4.4
Very good (29 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
Sep 1 - Sep 29
-56%
$11,706
$5,105 for 28 nights
House ∙ 8 guests ∙ 3 bedrooms

House in Siesta Key with Ample Parking

4.5
Excellent (35 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
Sep 21 - Oct 19
-21%
$5,281
$4,180 for 28 nights
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Sarasota with Pool, Yard & Patio

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 (67 ratings)
Siesta Key, Sarasota County, Florida, United States
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Apartment Siesta Key
$6,252 for 28 nights
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment in Lido Key with Grill & Pool

4.7
Excellent (66 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$7,250 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Siesta Key with Sauna, Pool & Grill + Gulf View

4.4
Very good (6 ratings)
Siesta Key, Sarasota County, Florida, United States
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Apartment Siesta Key
$5,572 for 28 nights
Apartment ∙ 2 guests ∙ 1 bedroom

Lovely Rental Apartment in Siesta Key

4.5
Excellent (31 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$14,168 for 28 nights
House ∙ 8 guests ∙ 4 bedrooms

Family Friendly House in Southgate with Grill, Pool & Yard

4.7
Excellent (14 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

4.7
Excellent (63 ratings)
Siesta Key, Sarasota County, Florida, United States
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Apartment Siesta Key
$6,204 for 28 nights
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Lido Key with Grill & Pool

4.7
Excellent (22 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$21,057 for 28 nights
House ∙ 14 guests ∙ 6 bedrooms

Vacation Home in Sarasota

Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
$11,603 for 28 nights
House ∙ 24 guests ∙ 8 bedrooms

House in Sarasota with Private Parking

4.9
Outstanding (132 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
$8,775 for 28 nights
Condo ∙ 7 guests ∙ 3 bedrooms

Condo in Siesta Key with Yard, Patio & Pool

4.7
Excellent (6 ratings)
Siesta Key, Sarasota County, Florida, United States
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Apartment Siesta Key
$5,132 for 28 nights
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Lido Key with Grill

4.9
Outstanding (35 ratings)
Siesta Key, Sarasota County, Florida, United States
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Condo Siesta Key
$7,625 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Standard Condo in Siesta Key with Grill, Patio & Pool

4.8
Outstanding (80 ratings)
Siesta Key, Sarasota County, Florida, United States
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Stay Cool: Monthly Rentals with Air Conditioning

Condo  Siesta Key
$13,474 for 28 nights
Condo ∙ 8 guests ∙ 2 bedrooms

Wonderful Condo in Siesta Key with Patio, Pool & Grill + Close to Beach

4.2
Very good (28 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Condo  Siesta Key
$4,478 for 28 nights
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Gulf Gate Estates with Pool

Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Apartment  Siesta Key
$6,178 for 28 nights
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment in Lido Key with Grill & Pool

4.7
Excellent (35 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Soak Up the Sun: Monthly Rentals with Patios

Apartment  Siesta Key
$7,058 for 28 nights
Apartment ∙ 2 guests ∙ 1 bedroom

Nice Rental Apartment in Lido Key with Screened-In Patio

4.5
Excellent (58 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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House  Siesta Key
$9,800 for 28 nights
House ∙ 8 guests ∙ 3 bedrooms

House in Sarasota with Patio, Yard & Grill

5.0
Outstanding (15 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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Villa  Siesta Key
$7,812 for 28 nights
Villa ∙ 5 guests ∙ 2 bedrooms

Villa in Sarasota with Patio, Pool & Yard

4.9
Outstanding (64 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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Stay connected: Monthly Rentals with internet

Condo  Siesta Key
$11,711 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Patio, Pool & Grill

4.7
Excellent (58 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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View deal
House  Siesta Key
$11,580 for 28 nights
House ∙ 8 guests ∙ 2 bedrooms

Vacation Home in Siesta Key with Grill & Yard + Next to Beach

4.6
Excellent (63 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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Condo  Siesta Key
$7,402 for 28 nights
Condo ∙ 6 guests ∙ 2 bedrooms

Beautiful Condo in Siesta Key with Grill, Pool & Sauna

3.9
Good (28 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

House Siesta Key
$30,279 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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House Siesta Key
$16,204 for 28 nights
House ∙ 8 guests ∙ 4 bedrooms

Lovely House in Siesta Key with Private Garage

5.0
Outstanding (14 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
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House Siesta Key
$31,266 for 28 nights
House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Siesta Key with Screened-In Balcony + Water Views

5.0
Outstanding (6 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! September is the most affortable time to stay in Siesta Key with a big group, when nightly prices for Monthly Rentals will range from $349 to $585 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 $433 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 $138 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 201 m²
💳 Highest rates in March
🛏️ 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

Siesta Key Monthly Rentals: What is the cost of a stay?

On average, you can get a great vacation home from $349 and get discounts up to 66%!

Can I find a vacation rental for a large group for Siesta Key Monthly Rentals?

in Siesta Key, large groups should consider House rental since they usually fit 8 people.

How many home rentals in Siesta Key are available for a month or longer?

There are more than 6,351 homes to rent in Siesta Key. The best time to find availability for longer stays is in September when home rentals have high availability.

What kinds of vacation rentals can i book for Siesta Key Monthly Rentals?

We would suggest browsing our incredible selection of House rental and Apartment rental for Siesta Key Monthly Rentals.

How much does a vacation home rental in Siesta Key cost per month?

Rates for a longer stay in vacation rental in Siesta Key range from $138 per night, but many hosts can offer discounts for stays of 14 days or longer.

Can you find seasonal vacation rentals in Siesta Key offer a pool?

Of course, more than 79% of accommodations in Siesta Key offer a pool.

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