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.
Distance to beach: 300 feet to Siesta Beach
Key Amenities
About this property
This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes...
Featured review
We had a great week despite the heat of summer. This house although dated was clean, cool and comfortable. It was a two minute walk through the back yard to the sand. We had a few minor house keeping...
Key Amenities
About this property
Very nice 4 Bedroom home on a canal just about 5 blocks to Siesta Village. offering: 1 car garage, Duet washer/dryer, Private pool, decorated with a Island flare. Tile throughout with granite and stainless steel kitchen appliances. Beautiful setting pool and patio overlooking canal with boat dock. (Boat...
Distance to beach: 0.5 miles to Siesta Key Beach
Key Amenities
About this property
Fern Haven studio bungalow is a Key West-style studio efficiency. It is comfy, cozy, bright, and airy, with French doors onto a deck overlooking gardens and a brick patio dining area. It has a large mirrored doored closet and under-bed drawers for ample storage. The kitchen is fully equipped with all...
Featured review
This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where...
Distance to beach: 0.3 miles to Siesta Key Beach access 10
Key Amenities
About this property
Welcome to Garden Terrace. Situated in the quiet and welcoming neighborhood of Palm Island, the heart of Siesta Key, this Tommy Bahama-styled studio efficiency has fifteen-foot sliding glass doors looking into a private brick courtyard with flowered trellis and wrought iron patio furniture. Wood and...
Featured review
I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key...
Key Amenities
About this property
* Please Note: The exact home location is not shown on the map. Message us for the exact address*Siesta Key Canal Oasis – Walk to Village & Beach!This private single-family home offers the perfect Siesta Key experience — located just a 1-minute walk to Siesta Key Village and a...
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Distance to beach: 0.3 miles to Siesta Key Beach
Key Amenities
About this property
Tropical Hideaway – Your Private Oasis in Siesta KeyEscape to the serene beauty of Siesta Key with a stay at the Tropical Hideaway, a secluded 2-bedroom, 1.5-bath bungalow nestled in the heart of the tranquil Palm Island neighborhood. Just a short stroll from the pristine Siesta Key Beach and...
Featured review
Choose this home for its fantastic location, hosts and amenities - easy walk to the beach or downtown Siesta Key, but feels miles away from the crowds in its tropical setting.The home was perfect for...
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