10 Best Monthly Rentals In Siesta Key, Florida - Updated 2024

Louise
Louise 
Updated
| 4 min read

Blessed with the beauty of the Gulf of Mexico, Siesta Key is a slice of heaven on Earth and a fabulous destination for nature lovers, sun-seekers, and watersports enthusiasts. This Sunshine State barrier island is home to Siesta Key Beach - a family-friendly public beach with sports facilities and a playground that kids love. The Crescent Beach boasts magical sunset views that you can not miss seeing while holidaying here. At Turtle Beach, you can enjoy picnics with your loved ones and watch nesting turtles. With a destination as action-packed as Siesta Key, it is no surprise that visitors never want to leave - or stay longer than planned. If you’re planning a long-term holiday here, be sure to book the right accommodation for you. Browse this list of the best monthly rentals in Siesta Key, Florida.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.

1. Casa Berano (from USD 390)

Attracting meticulous vacationers, this Airbnb is tastefully curated with bright and sunny interiors and a vibrant interior design, echoing Mediterranean ambiance. Here, you can enjoy standard home fittings, such as an equipped kitchen, a living room with a Smart TV, and spotless baths. You’ll have a patio, which is the perfect spot for morning coffee, and a swimming pool, ideal for any time of the day.

Casa Berano strictly allows six guests only. Up to two dogs can be accommodated. If you’re interested in this property, note that it has a 7-night minimum stay policy, and month-long stays are rewarded with a discount.

Stayed at this property?
Siesta Key, Florida, United States
103 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
it is very comfortable and has all the amenities needed for a perfect vacation
amazing home such an incredible location with incredible amenities the pool and grill outside were excellent to have
from little touches such as hand sanitizer and the most comfortable bed ever
the screened lanai and pool are perfect as was the grill
the pool is a nice size (deepest being about 5ft) with beautiful tropical foliage canopying it
Cleanliness:
house was super clean
the property was also clean upon our arrival
the house was sparkling clean and more than comfortable
the house was very clean and well set up for our family
well stocked clean and the pool was a plus
Host:
debi and cage are wonderful hosts and readily available
the hosts cage and debi take their roles as super hosts seriously
wonderful space and amazing hosts
the owners were responsive to any questions about the house or area
cage & debi are very responsive and wonderful hosts
Location:
location to everything was great
amazing house in a great location
this a great location and great value
great location just minutes from the beach and village
location is great only minutes from siesta beach and downtown
Read more reviews

2. Sea Club II Garden House (from USD 314)

This Airbnb is a freshly renovated beach bungalow showcasing rustic flooring, modern decor, and stainless-steel appliances. When some of you are preparing meals in the well-equipped kitchen, the rest of the pack can watch movies in the living room or browse the web to their hearts’ content. A washer and a dryer are available in this air-conditioned dwelling for added convenience, and you can find a bathtub here, too. In your leisure time, you can enjoy fresh air on your private deck or indulge in refreshing laps in the community pool.

This accommodation can be booked for as short as a three-night stay. Those on an extended holiday can enjoy monthly discounts.

Stayed at this property?
Siesta Key, Florida, United States
119 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
loved the living room with wrap around couch
the pool was great and not crowded and the communal grills were brand new and nice
the space is updated stylish and comfortable
we only touched one of the beds the master bedroom and it was firm and comfortable
Cleanliness:
clean and spacious condo
very clean and beautifully furnished
the house was very clean and just as described
everything was very clean and the beds were super comfortable
it was very clean and everything we needed was there and then some
Host:
the home was spectacular and the hosts were wonderful
host was very helpful and got back to us with any questions we had very prompt
everyone we met was friendly
host responded within and hour or so to questions which is nice
the list of grocery stores with addresses was very helpful too
Location:
the location is great
the location was great
great condo in a good location
the location was fabulous
great place and location for family vacation
Read more reviews

3. Tourist-friendly abode with a pool and a hot tub (from USD 319)

Suitable for long-term stays, this property has a minimum 14-night stay policy. It can accommodate month-long stays, as well. The property boasts a fully furnished interior design and a tourist-friendly location, steps from the white-sand Siesta Key public beach. An outdoor pool is available on the premises, should you prefer to stay at home for the day. There’s also alfresco dining and barbecue equipment for your cookouts. A hot tub is a bonus.

Stayed at this property?
Sarasota, Florida, United States
PRIVATE VACATION HOME 6 Guests 2 Bedrooms 3 Bathrooms

Top guest reviews
Cleanliness:
the house was clean and very comfortable in a quiet neighborhood
the house is cozy clean and comfortable
Host:
boo & mike were attentive & gracious hosts
had a great time and the owners were fun to meet
Location:
i loved the location of this house it’s great proximity to the beach
beautiful property close to the beach
beautiful siesta beach is a five minute walk away
we had a wonderful time at this location
Read more reviews
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4. Pin Oaks Cottage (from USD 131)

A tourist-friendly abode with an Old Florida vibe, Pink Oaks Cottage is nestled in Sea Club 2, within proximity to Siesta Key Beach and Crescent Beach. Shops and dining spots are easily reachable on foot from this accommodation, making it loved by past guests even more. In addition to a kitchen, air-conditioning, and laundry facilities, the humble abode provides WiFi - a sure hit with most people staying for a month or more.

This rental can accommodate both short-term stays and month-long holidays.

Stayed at this property?
Siesta Key, Florida, United States
cottage 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
pool area was great with beautiful views of the intercoastal waterway
very comfortable unit in an exceptional setting
Cleanliness:
house was very clean as well as the grounds
Host:
property manager rae is very responsive to any questions or requests
Location:
cute little cottage in a nice location not far from the beach
there also are free shuttle buses
location by the water and pool is great
old florida charm :)cozy cottage close to main beach
Read more reviews
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5. Three-story dwelling with a modern kitchen (from USD 780)

This superb accommodation is a wise choice for families, as it can accommodate up to eight guests, and a small, well-behaved fur baby can be allowed. The three-story property is modernly furnished with stainless-steel kitchen facilities, air-conditioning, and heaps of natural light. Business travelers can enjoy free WiFi, and a private pool and a hot tub are available for lazing out.

This family-friendly accommodation imposes a 15-night minimum stay. Month-long stays can also be accommodated - with discounts.

Stayed at this property?
Sarasota, Florida, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 6 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
pool and hot tub are great
Host:
the local manager was super responsive
the property management was always friendly and available and quick to respond to any questions or concerns
the property manager was extremely helpful and nice
property manager was responsive and great to work with as was the owner
would recommend this property and definitely would stay with this host again did not want to leave
Location:
perfect location for a beach getaway with family
the walk into the village is a little bit more of a walk but definitely doable
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

6. Fully furnished two-bedroom abode (from USD 225)

Are you seeking comfortable and convenient accommodation in Siesta Key that can host you for a month? Check out this two-bedroom apartment that can accommodate weekly and long-term stays. Discounts are afforded to month-long guests.

Since it is fully furnished, you can expect a kitchen, laundry appliances, and WiFi. A private pool and a hot tub are delightful additions. In the mood for a saltwater soak? The beach can be reached on foot in eight minutes.

Stayed at this property?
Sarasota, Florida, United States
PRIVATE VACATION HOME 6 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Cleanliness:
very clean comfortable and neat facility
rental was very roomy and clean
the place is clean conveniently located and my kids love the private pool
Host:
this is an amazing property with a great host
the hosts were nice and very easy to work with
the house & hosts were great the house is everything i expected and exactly as advertised
Location:
the location is ok as well about a half mile walk to the village
the property is in a good location closeto beaches restaurants and the siesta village
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

7. Superb apartment with alfresco dining (from USD 399)

For a minimum of seven nights’ stay, you can take advantage of this thoroughly sanitized property. It also seasonally welcomes month-long stays, in case you’re on a long-term business trip in Siesta Key. This beautiful abode showcases an open-plan layout with an elegant kitchen, a cozy living space with a Smart TV, and a six-seater dining set. There’s alfresco dining with a gas grill for your barbecues, as well.

Guests of the apartment can access the community clubhouse and the pool. The beach can be reached in four minutes on foot.

Stayed at this property?
Sarasota, Florida, United States
villa 6 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
beautifully renovated kitchen that was fully stocked
Cleanliness:
pool was clean and very accessible condo was well kept and spacious
spacious and clean in a well cared for community
the unit was very spacious and comfortable
very clean excellent patio and seating
Host:
house was very clean owner was able to answer questions quickly and was very helpful
Location:
the location is great so that the walk to the beach was only about 5 min
we loved our stay here excellent location close to the beach and right next to the pool and laundry
didn’t care much for the beach within walking distance but loved turtle beach
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

8. Pet-friendly dwelling with WiFi (from USD 350)

Long-term holidayers will love this tropical vacation rental, offering a discount for month-long bookings. Apart from the generous price slash, the location, steps from Siesta Key Beach, thrills patrons. The fully furnished concept is worth appreciating, as well. You can whip up your favorite meals daily, access the web, and bring up to two beloved little pooches. Do note that a pet fee will apply.

The best part? A heated swimming pool tucked in tropical foliage awaits in the backyard.

Stayed at this property?
Siesta Key, Florida, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Cleanliness:
quiet clean and just perfect for our needs
quiet clean and just perfect for our needs
the property was very clean and very well equipped we didn't want for anything
Host:
met the owners briefly friendly as expected from our mail communication
met the owners briefly friendly as expected from our mail communication
the house was well-stocked well-appointed and owners very thoughtful about all the details
Location:
the house is in the most perfect location near the beach and the village
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

9. Freshly remodeled villa with pool access (from USD 169)

This posh villa is suitable for beach-goers, as it is within arm’s reach of Siesta Key. It also offers a freeform pool, where you can take a plunge as soon as you exit your lovely little abode. Suitable for a pair of travelers, this VRBO is equipped with a king-size bed, an open kitchen, and a seating area with a wide-screen TV. Since the internet is accessible here, you can enjoy a work-from-home setup.

Note that this accommodation has a varying minimum stay policy, but month-long stays are welcome, and discounts are available.

Stayed at this property?
Sarasota, Florida, United States
PRIVATE VACATION HOME 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
the air conditioner worked a little too well but that’s a good thing
small pool was great as an alternative to the beach
Cleanliness:
the property was clean and super cute
our rental was clean tidy and had everything we needed
a little off the beaten path but nice easy beach access clean people were nice
Location:
it was a cute little place located in a nice spot with a short walk to the beach
great condo in a fantastic location will be back again
the short drive to shops and restaurants made this a great location
great location can walk to the beach and also restaurants and bars
we had easy access to the public beach with a very short walk
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

10. Modern apartment with sea views

This apartment’s top-selling factor is its location, a stone’s throw away from Siesta Key Beach. Its well-curated modern design is a good selling point, too. Wooden floors, white walls, and expansive windows make the look of this cozy retreat. For convenience, a kitchen, a dining area with a view, and WiFi are at your service. Access to a gym and a heated outdoor pool are included in the rate.

Whether you are staying for a week or a month, you are welcome to avail yourself of this superb rental. Month-long stays can enjoy discounts.

Stayed at this property?
Siesta Key, Florida, United States
44 reviews   Superhost Wifi Available
ENTIRE CONDO 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
furniture and beds comfortable
the pool is very nice with plenty of chairs loungers and tables with umbrellas
Cleanliness:
it was clean and cozy
the pool is very clean
overall condo was clean cute and comfortable for our family of 4
Host:
the owner was a pleasure to deal with from the start and easy to communicate with
carlos is a great host sal property manager was great as well hope to return soon
again not the owner's fault
i can’t say enough good things about this condo the owner and the property managers
only a few minutes walk across the street sal the property manager was very friendly and accommodating
Location:
perfect location near the beach
great location that need some tlc
excellent location right across from the beach—walking distance to everything
easy walk to the beach
great place with great location and nice pool
Read more reviews

Have a fun-filled holiday in Siesta Key

Siesta Key is a gorgeous and fun-filled destination that deserves a month-long visit. It is packed with exciting recreational areas, from natural ones to man-made ones. To make your long-term stay comfortable, be sure to choose accommodation from this list of the best monthly rentals in Siesta Key, Florida.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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