Siesta Key Monthly Rentals - HomeToGo base64Hash Siesta Key Monthly Rentals - HomeToGo

Siesta Key Monthly Rentals

Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Bedrooms

    • Any
    • 1 bedroom
    • 2+ bedrooms

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Balcony/patio
    • WiFi
    • Air conditioning
    • Kitchen
    • Washing machine
    • TV
    • Parking
    • Microwave
    • Dishwasher
    • Hot tub
    • Yard
    • Sauna
    • Fireplace
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Siesta Key Monthly Rentals: Recommended rentals

Siesta Key Monthly Rentals: find your perfect rental from just $104 per night!

House Siesta Key
-35%
Apr 26 - May 24
House ∙ 11 guests ∙ 5 bedrooms

Vacation Home with Barbecue & Private Pool

Siesta Key, Sarasota County, Florida, United States
$817$490
per night
Excellent(105 ratings)
$817$490
per night
View deal
Cottage Siesta Key
Feb 1 - Mar 1
Cottage ∙ 5 guests ∙ 5 bedrooms

Fully Equipped Cottage with Grill & Pool | Pets Allowed

Siesta Key, Sarasota County, Florida, United States
$275
per night
$275
per night
View deal
House Siesta Key
Nov 2 - Nov 30
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Grill, Private Pool & Yard | Suitable for Remote Work

Siesta Key, Sarasota County, Florida, United States
$225
per night
Outstanding(5 ratings)
$225
per night
View deal
House Siesta Key
Nov 2 - Nov 30
House ∙ 12 guests ∙ 4 bedrooms

House with Garden, Private Pool & Patio

Siesta Key, Sarasota County, Florida, United States
$455
per night
Excellent(62 ratings)
$455
per night
View deal
Condo Siesta Key
-18%
Nov 2 - Nov 30
Condo ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Beautiful Condo with Heated Pool, Patio & Yard | Nature View | Beach Nearby

Siesta Key, Sarasota County, Florida, United States
$354$243
per night
Very good(30 ratings)
$354$243
per night
View deal
House Siesta Key
Jul 16 - Aug 13
House ∙ 28 guests ∙ 8 bedrooms

House with Terrace, Yard & Private Pool

Siesta Key, Sarasota County, Florida, United States
$422
per night
Outstanding(146 ratings)
$422
per night
View deal
House Siesta Key
Jul 3 - Jul 31
House ∙ 6 guests ∙ 3 bedrooms

Children-Friendly House with Terrace & Garden | Good for Workation | Pets Allowed

Siesta Key, Sarasota County, Florida, United States
$145
per night
Outstanding(3 ratings)
$145
per night
View deal
Villa Siesta Key
Feb 1 - Mar 1
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with Pool

Siesta Key, Sarasota County, Florida, United States
$229
per night
$229
per night
View deal
Apartment Siesta Key
Jul 3 - Jul 31
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment with Heated Pool, Grill & Patio

Siesta Key, Sarasota County, Florida, United States
$500
per night
Outstanding(2 ratings)
$500
per night
View deal
House Siesta Key
-37%
Apr 26 - May 24
House ∙ 6 guests ∙ 4 bedrooms

House with Private Pool, Grill & Patio

Siesta Key, Sarasota County, Florida, United States
$995$429
per night
Outstanding(58 ratings)
$995$429
per night
View deal
House Siesta Key
Jul 16 - Aug 13
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Barbeque & Terrace

Siesta Key, Sarasota County, Florida, United States
$367
per night
Outstanding(134 ratings)
$367
per night
View deal
House Siesta Key
Nov 2 - Nov 30
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Barbeque, Private Pool & Patio | Nature View

Siesta Key, Sarasota County, Florida, United States
$1,016
per night
Outstanding(27 ratings)
$1,016
per night
View deal
Apartment Siesta Key
Jul 3 - Jul 31
Apartment ∙ 5 guests ∙ 3 bedrooms

Rental Apartment with Barbeque & Pool | City View

Siesta Key, Sarasota County, Florida, United States
$228
per night
Outstanding(30 ratings)
$228
per night
View deal
House Siesta Key
-29%
Jul 3 - Jul 31
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Private Pool, BBQ & Garden | Nature View

Siesta Key, Sarasota County, Florida, United States
$1,166$681
per night
Outstanding(128 ratings)
$1,166$681
per night
View deal
Apartment Siesta Key
Jul 3 - Jul 31
Apartment ∙ 2 guests ∙ 1 bedroom

Wonderful Rental Apartment with Pool | City View

Siesta Key, Sarasota County, Florida, United States
$107
per night
Outstanding(6 ratings)
$107
per night
View deal
Show all 8,905 properties

Popular amenities for Siesta Key Monthly Rentals

Find the perfect home for your stay

Monthly Rentals with pools

Pet-Friendly Monthly Rentals

Monthly Rentals with patio

Monthly Rentals with internet

Top-rated monthly rentals in Siesta Key

Browse our top rated monthly rentals offers

Condo Siesta Key
Jul 3 - Jul 31
$127
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with BBQ, Patio & Pool

4.6
Excellent(71 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Apr 26 - May 24
$490
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-Friendly Pleasant Vacation Home with Barbecue, Private Pool & Patio | Pet-Friendly

5.0
Outstanding(53 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Jul 3 - Jul 31
$944
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Private Pool, Terrace & Jacuzzi | Perfect for Remote Work

4.9
Outstanding(45 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Best Deals and Discounts on Monthly Rentals

Save up to 40%

Condo Siesta Key
Oct 4 - Nov 1
-33%
$384
$265
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Grill & Heated Pool | Nature View

4.9
Outstanding(68 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Oct 4 - Nov 1
-40%
$357
$201
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Lovely Condo with Barbecue | Beach Nearby

4.7
Excellent(87 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Oct 4 - Nov 1
-23%
$936
$562
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home with Grill | Beach Nearby

4.9
Outstanding(69 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Budget-friendly monthly rentals in Siesta Key

Our top value vacation rentals for monthly rentals

Condo Siesta Key
Jul 3 - Jul 31
$224
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with Heated Pool, BBQ & Yard | Nature View

5.0
Outstanding(1 rating)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Jul 3 - Jul 31
$579
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Ample House with BBQ, Garden & Private Pool | Nature View | Perfect for Remote Work

5.0
Outstanding(59 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Jul 3 - Jul 31
$465
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Family-Friendly Condo with Barbecue, Heated Pool & Sauna | Nature View | Next to the Beach

5.0
Outstanding(45 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Stay Cool: Monthly Rentals with Air Conditioning

Condo Siesta Key
Jul 3 - Jul 31
$237
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Children-Friendly Pleasant Condo with Terrace, Heated Pool & Barbeque | Close to the Beach

4.8
Outstanding(164 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
House Siesta Key
Jul 3 - Jul 31
$382
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully Equipped Vacation Home with Pool | Close to the Beach

4.3
Very good(8 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
Apartment Siesta Key
Jan 11 - Feb 8
$177
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment with Terrace

4.8
Outstanding(39 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
See all offers

Soak Up the Sun: Monthly Rentals with Patios

Cottage Siesta Key
Oct 16 - Nov 13
-52%
$333
$145
per night
Cottage ∙ 3 guests ∙ 1 bedroom

Cottage with 1 Room for 3 Persons

5.0
Outstanding(1 rating)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Balcony/Patio
View deal
House Siesta Key
Jul 3 - Jul 31
$366
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-Friendly House with BBQ, Yard & Private Pool | City View | Good for Workation

5.0
Outstanding(32 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
Condo Siesta Key
Jul 3 - Jul 31
$389
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with BBQ, Terrace & Heated Pool | Good for Workation

5.0
Outstanding(16 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
See all offers

Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Apartment Siesta Key
Jul 14 - Aug 11
$225
per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Rental Apartment with Jacuzzi & Pool

4.4
Very good(3 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
View deal
Condo Siesta Key
Jul 3 - Jul 31
$329
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Condo with Pool, Terrace & Jacuzzi | Nature View | Next to the Beach

4.3
Very good(78 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
May 3 - May 31
-72%
$2,239
$619
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-Oriented Vacation Home with Private Pool, Hot Tub & Barbeque | Beach Nearby | Good for Workation | Dogs Allowed

5.0
Outstanding(17 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
View deal

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 $308 to $697 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 $794 per day for a family of 9 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 $104 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

📏 Average home size 106 m²
💳 Highest rates in February
🛏️ Popular home types Condo and House rental
🌡️ Hottest months 91 °F in August and June
❄️ Coldest months February and January
🌧️ Rainiest months August and July

Siesta Key Monthly Rentals: frequently asked questions

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

The average rate for a rental in Siesta Key is between $308 and $697 per night.

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

Condo in Siesta Key can fit 5 guests.

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

There are more than 8,905 accommodations to rent in Siesta Key. The best time to find availability for longer stays is in May when home rentals have high availability.

Siesta Key Monthly Rentals: what kinds of vacation rentals can I book in Siesta Key?

You can browse 2,261 House rentals and 2,708 Condos in Siesta Key on HomeToGo.

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

Rates for vacation rentals in Siesta Key over a longer period start from $104 per night, but many hosts can offer discounts for stays of 14 days or longer.

Can you find mid-term rentals in Siesta Key include a pool?

Definitely, more than 68% of accommodations in Siesta Key come with a pool.

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