Looking for a tropical getaway on Florida’s Gulf Coast? Our monthly rentals in Siesta Key offer the perfect long-term escape in one of the most beautiful beach destinations in the world. Whether you're planning a winter retreat or a summer vacation, Siesta Key’s pristine beaches, vibrant nightlife, and outdoor activities make it an ideal destination.
Key Amenities
About this property
This lovely penthouse condo is in one of Siesta Key's newest complexes (built in 2006). The Crescent offers luxury living at its finest. Bask in the spectacular view of the world famous Crescent beach on Siesta Key from this three (3) bedroom, three (3) bath beach front condominium's open air ...
Key Amenities
About this property
Home away from home.... I enjoy my coffee and cocktails at waterfront lanai and when I travel, I would love someone to enjoy it as well. I live in this condo, therefore, this unit has everything you may need and more. Boating, fishing, paddle boarding, kayaking, biking to Siesta Key Beach or free trolley ...
We’ve been vacationing in Sarasota/Turtle Beach for over 10 years. This condo is our ABSOLUTE FAVORITE! Very nicely decorated & accommodating. We love that it is located on the bay. It is GREAT for fishing ...
Key Amenities
About this property
This 3600 sq ft., 5 Bedroom 3.5 Bath, Townhome Offers, Private heated pool, ** Please be aware that the pool is refreshing, but has limited space for larger parties. many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. LAYOUT of the HOUSE : Ground floor off the pool ...
Key Amenities
About this property
SIESTA KEY.GETAWAY Experience a luxury condo with a view. Located on the world renowned Crescent Beach at Siesta Key. Gulf and Bay Club is a 32 acre resort community with exceptional beach access, top notch amenities and amazing sunsets. 6 pickle ball courts. 5 hard court, 1 clay tennis courts. Gym. ...
Our family had the pleasure of staying at this Gulf and Bay rental on more than one occasion. The condo is a hidden gem with a spectacular view, and just steps away from the beach. We could not have asked ...
Key Amenities
About this property
This 3400 sq ft., 5 Bedroom 3 Bath, Townhome Offers, Private heated pool- **please keep in mind the pool is refreshing, but has limited space for larger parties. Many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. (REVISED LAYOUT of the HOUSE : Effective: Oct. 2019 ...
Explore a range of monthly rentals in Siesta Key, from beachfront condos to luxurious homes with ocean views. Whether you want to be close to Siesta Beach or prefer a quiet retreat near Crescent Beach, there’s a rental to suit your needs. Enjoy the comfort of a long-term stay in this coastal paradise.
Don’t wait to secure your ideal long-term rental in Siesta Key. Browse our listings and find the perfect property for your extended stay. Whether you’re looking to escape the cold or enjoy a warm, sunny vacation, Siesta Key is the place to be.
Booking in advance is the best way to ensure you get the rental you want, especially during the busy winter months when Siesta Key is in high demand.
Group-Friendly Rentals
Planning a group vacation or family reunion? Siesta Key offers spacious rentals with multiple bedrooms and large living spaces, perfect for groups looking to enjoy a relaxed beach getaway.
Family-Friendly Monthly Rentals
Siesta Key is ideal for families with attractions like Siesta Beach, Point of Rocks, and Turtle Beach. Our family-friendly rentals provide ample space, outdoor areas, and proximity to kid-friendly activities like boating, snorkeling, and wildlife viewing.
Romantic Getaways for Couples
Siesta Key’s romantic sunsets and tranquil beaches make it a great destination for couples. Enjoy cozy monthly rentals with ocean views, private pools, and easy access to intimate dining and beachside strolls.
Winter Retreats for Snowbirds
Siesta Key is a favorite among snowbirds seeking to escape the cold northern winters. With its warm weather, stunning beaches, and a laid-back atmosphere, it’s no wonder snowbirds flock here each winter. Our monthly rentals provide a comfortable and convenient home base for an extended stay.
Don’t miss out on your chance to spend the winter in paradise! Reserve your long-term rental in Siesta Key today and enjoy everything this beautiful destination has to offer.
Siesta Key is known for its stunning beaches and outdoor adventures. Staying in one of our monthly rentals puts you close to:
💰 Highest rates
December through March
🎉 Busiest month
February
🏠 Popular home types
Beachfront condos and single-family homes
🔥 Hottest months
July and August
❄️ Coldest months
January and December
☔ Rainiest months
June through September
🌺 Best months for flowers
April and May
🌴 Peak tourist season
December through March
🍂 Quietest months
September and October
🌊 Best beach months
March through May
🏌️ Best golfing months
November through April
🎨 Top cultural events
Siesta Key Crystal Classic Sand Sculpting Festival (November), Siesta Fiesta Art Festival (April)
🍽️ Best dining months
January through March
🦋 Best months for nature activities
March through May
🛶 Best water sports season
June through September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
November through April
