Siesta Key Last Minute Vacation Rental Deals

When a beach getaway infused with luxury and style sounds like a refreshing change of pace, you'll find everything you need when you book Miramar for your next trip this way. Miramar is a welcoming 4-bedroom, 3.5-bath home away from home that can accommodate up to 11 guests at a time. Whether your plans bring you here with a group of friends in tow or you're excited to spend quality time with the entire family, booking a stay in Miramar keeps you close to area fun while making the most of comfor.......

4.8 Star Review

Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very large open layout with plenty of space for entertaining. In the back this vacation rental home has a large private screened-in solar heated pool and lanai. Kids can play outside on the grass backyard. The.......

4.8 Star Review

Discover your dream vacation rental in the heart of Siesta Key, Florida, where coastal charm meets modern luxury. This stunning home offers the ultimate getaway, just a short walk to the pristine Siesta Key Beach and vibrant village with dining, shopping, and nightlife. Step inside to find a spacious, light-filled living area designed for comfort and relaxation. The main floor features a dining area with towering 20+ foot ceilings and massive windows, a gourmet kitchen equipped with stainless st.......

5.0 Star Review

This 2 bedroom 2 bath unit is located on the intercostal and just 1 mile south of Siesta Key public beach. There are no stairs to worry about here! With this unit you are on the ground floor steps to the parking lot, heated pool, and community facilities. Enjoy beautiful views of the intercostal from the pier or walk to Siesta Key public beach approx. 1 mile north or Beach Access 1/2 mile south. Lush tropical landscaping throughout the complex gives Bay Oaks a unique relaxing feel. Minimum age t.......

4.6 Star Review

Enjoy this updated townhome within walking distance to Siesta Key's main beach. The property is located within a resort style gated community offering two heated swimming pools, tennis courts, fitness room, gas BBQ grills, and fishing dock. All this nestled among lush tropical landscape and lakes. Arrive by car and utilize the garage or driveway for parking. Taking the stairs up to the second floor of the townhome, you enter through the front door into the home. Right away you will notice the up.......

4.8 Star Review

Siesta Key has been named America's #1 beach time and time again. Experience fun in the sun like never before at this two-story townhome style condo located just a few hundred feet from the private access beach. Towards the front of the community guests have access to a heated pool and bathrooms. Walking up to the unit you will walk past an outdoor patio with a patio dining set. Enter through the front door and find yourself in the living room of this updated unit. Plenty of seating with an almo.......

4.5 Star Review

A sunny Siesta Key adventure is made even better for those who book a stay in beautiful Beach Road. This welcoming 2-bed, 2-bath home away from home offers up enough space to accommodate 6 guests at a time making it an ideal property for a group of friends or a family getaway. Beach Road enjoys a prime location directly across the street from Siesta Key Beach and is only mere blocks from exciting stops like Siesta Key Village. Whether you're looking to cozy up or head out and enjoy the best of l.......

4.8 Star Review

When taking time to unwind with a healthy dose of sand, sun, and surf is exactly your style, Siesta Key is the place to be, and Beach Road-Bari should most definitely be your home away from home! This welcoming rental property features a bedroom and bathroom within a floorplan that's fantastic for welcoming up to 3 guests at a time. Beach Road-Bari is an inviting beach side studio that pairs amazing amenities with proximity to fun. When comprehensive Siesta Key living is a priority, Beach Road-B.......

4.7 Star Review

Just knowing you have a scenic trip to Siesta Key on the calendar is exciting. Knowing you've booked your stay in Beach Road-Capri only makes it that much better! This vacation home away from home is a charming beachside property featuring 1-bath studio within a floorplan that's fantastic for welcoming up to 4 guests during a stay. Whether you're headed to Siesta Key for a solo adventure, can't wait to spend time with your significant other or have a small group trip planned, Beach Road-Capri of.......

4.7 Star Review

There's nothing more refreshing than knowing you get to spend time in sunny Siesta Key. When you have a trip on the calendar and can't wait to make the most of every moment, booking your stay in Beach Road-Tropea is a must! This 1-bed, 1-bath abode is ideal for welcoming up to 4 guests at a time. That means that whether you're in town on an independent adventure, traveling with a significant other or enjoying a small group getaway, Beach Road-Tropea promises to be a home away from home that pair.......

4.8 Star Review

Take a look at this spacious canal front home on Siesta Key with heated pool. This home is great for a large family or even two families with its open floor plan. Enter the home through the double French doors and down the foyer into the heart of the home; the open family room, living room w/ fireplace, and eat-in kitchen. Large sliding glass doors run the entire length of the home looking out over the pool, backyard, and canal. The master bedroom offers a king-size bed and flat screen TV with o.......

5.0 Star Review

Making the most of a sunny getaway starts with booking Holiday House 1 the next time travel plans bring you to scenic Siesta Key. This inviting 1-bedroom, 1-bath abode is a welcoming place for up to 4 guests at a time to enjoy. Whether you're headed here with family, friends, or a significant other, Holiday House 1 puts you in the heart of the Florida fun. This property is just a walk away from the sandy shores of Siesta Key Beach and provides impeccable amenities to enjoy when you're cozied up .......

4.7 Star Review

Spending time in Siesta Key is always an exciting experience. However, those who choose to book a stay in Holiday House 2 will find that accessing those area highlights you can't wait to explore is easier than ever! This inviting 1-bed, 1-bath home away from home can easily accommodate up to 4 guests at a time and sits just step from Siesta Key Beach. It's an ideal retreat for those who are traveling this way as a couple, or in a small group of family and friends. When you can't wait to enjoy a .......

4.8 Star Review

Never miss a beach-scape sunset when you are just a couple hundred meters from Americans #1 beach, Siesta Key Beach. Enjoy this two bedroom two bathroom condo style unit in a great location: a short walk to the beach on a quiet street but just minutes from shops, bars, and restaurants. The unit offers a full kitchen large enough for TWO cooks in the kitchen..., breakfast bar, an open dining area and living room. The living room is furnished with a flat screen TV. Open the large sliding glass doo.......

4.9 Star Review

Come and enjoy this two bedroom two bathroom condo style vacation rental located just a short walk to Siesta Key beach. The main living area has an open concept with living room and dining area in the first great room when you enter the unit. There is a full kitchen with breakfast bar opening off to the side of the dining room. The living room is equipped with a flat screen TV and has large glass sliding doors opening out to the screened balcony. The master bedroom is furnished with a king-size .......

4.8 Star Review

If you are going to visit the #1 beach in the country, then stay on the #1 beach! This two bedroom, two full bathroom beachfront condo is located on Siesta Key Beach and is only steps from the soft white sands that Siesta Key Beach has to offer. It also includes a heated pool and a large balcony overlooking the beach. Surrounded by a beautiful tropical manicured palm tree landscape, this resort style beach condo offers all the amenities one could ask for to make the perfect beach vacation. The c.......

4.5 Star Review

When you're overdue for a refreshing vacation, a trip to Siesta Key is always a good idea. Making the experience even more exciting is the choice to book a stay in Midnight Cove II - Doveplum. This welcoming 3-bed, 2.5-bath condo can easily accommodate up to 6 guests at a time and provide proximity to area fun while also incorporating the comfort, style, and convenience every traveler deserves! Integrated into a complex that sits next to a lush lagoon, guests will find that whether they're visit.......

4.5 Star Review

When a beach-focused getaway is exactly your style and you can't wait to enjoy time in Siesta Key, booking One Ocean-A promises to be an inspiring choice. This inviting and conveniently located 2-bedroom, 1-bath property can accommodate up to 4 guests at a time and is situated a mere one block from the beach! Wake up each day of your stay knowing you're only steps from the waves and sand. One Ocean-A provides a collection of delightful amenities for guests to enjoy but is also within reach of gr.......

4.5 Star Review

Taking time to kick back and relax in beach-focused style is easy to do when you make your way to Siesta Key and book One Ocean-B to complete your adventure. This welcoming and colorful 2-bed, 1-bath home away from home is designed to welcome up to 4 guests at a time making it an amazing choice whether you're enjoying a Florida getaway with family or spending time with a group of close friends. One Ocean-B provides amazing amenities for guests to enjoy but also has the prime location to match. T.......

4.8 Star Review

Nestled along the serene waters of Heron Lagoon, our 1-bedroom suites at Siesta Heron Suites & Villas offer the perfect blend of comfort, convenience, and tropical relaxation. Whether you're planning a romantic retreat or a peaceful solo escape, our beautifully appointed suites provide everything you need for a memorable stay in Siesta Key, Florida. Spacious & Stylish Accommodations Step into a bright and airy living space, tastefully furnished with a cozy sofa and a flat-screen TV with streamin.......

4.8 Star Review

This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and roll-a-ways available on request for the living room accommodating up to four persons. The living room is furnished with a TV with HD programing. The kitchen is equipped with 4-burner gas cooktop, refrigerator, and convection oven/microwave among other small kitchen appliances. just outside your unit there is a small deck furnished with two chairs to sit out and possibly enjoy a coffee on a cool morni.......

4.7 Star Review

This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and roll-a-ways available on request for the living room accommodating up to four persons. The living room is furnished with a TV with HD programing. The kitchen is equipped with 4-burner gas cooktop, refrigerator, and convection oven/microwave among other small kitchen appliances. just outside your unit there is a small deck furnished with two chairs to sit out and possibly enjoy a coffee on a cool morni.......

4.8 Star Review

The Siesta Heron Suites & Villas enjoys a proximity that is close to the heart of everything that makes Siesta Key special, and our Sand Dollar unit is another ideal example. One bedroom, one bathroom, and a spacious and open living area allows up to four guests to live together in comfort and harmony. Spend your days exploring the beauty of Siesta Key and the mainland areas of nearby Sarasota and Bradenton, located just over the bridge, and spend your night in the welcoming rooms of Sand Dollar.......

4.7 Star Review

The last of our Siesta Heron escapes offers something extra the others don't and that is an extra bedroom. Key Lime, the fifth unit in this tranquil community is a 2-bedroom, 2-bathroom unit with room for 6 guests to cohabitate happily. Offering a private screened-in patio, it is a popular choice for travelers with slightly larger families. A sofa provides a comfortable place to read and relax on a lazy vacation day and the small table and chairs on the screened-in patio of Key Lime is an ideal .......

4.7 Star Review

When a vacation focused on fun under the sun is your goal and you're looking for amazing accommodations to meet the moment, booking a stay in is sure to inspire! This 2-bed, 2-bath home away from home can welcome up to 6 guests at a time making it an ideal option for those traveling with friends to Florida or looking forward to quality time enjoyed alongside family. Siesta Heron 6 offers guests access to a variety of stunning amenities and features to enjoy within as well as prime access to area.......

4.7 Star Review

Spending time in sunny Siesta Key is always a treat for travelers. Those looking to enhance their stay with the inclusion of amazing accommodations will find everything they're looking for and more in Siesta Heron 7 / Heron House! This welcoming 3-bed, 2-bath retreat can welcome up to 10-guests at a time making it a wonderful choice for those traveling with family or friends alike. The property sits just a mile from Turtle Beach and no more than 3 miles from Siesta Key Beach. The restaurants, sh.......

4.6 Star Review

Enjoy beach and pool days to the fullest at this two bedroom two bath updated vacation rental on Siesta Key. No need to worry about crowded beaches and circling for parking spots. Enjoy private beach access just a few steps away from this ground floor unit. The community offers outside patio seating just in front of the building and heated swimming pool. Utilize the islands free ride services and head down to SIesta Key Village, located just 1.5 miles away. Siesta Key Village is full of restaura.......

4.9 Star Review

*** NEW *** Siesta Key beach has become known world wide for its incredible miles of soft white sand beaches and small village type atmosphere. This property is located within a community situated on these very beaches. The community offers beach access to a less crowded semi-private beach, swimming pool, shuffle board, and camp style grills. With such a central location, Siesta Key Village and South Village are just a few minutes ride away utilizing the free island shuttle or free ride services.......

4.8 Star Review

The beauty of Siesta Key is renowned throughout the world and the charms found in our Siesta Beach House, Cottage B, reflect the spirit of the Key. Offering 3 bedrooms, 2 baths, and enough room for 8 visitors to happily cohabitate, its proximity to white sand beaches and a heated pool shared by other cottages in this community make it extra special! Shaded by palm trees and offering the traditional Florida vibe, Cottage B is destined to be the one you temporarily make your own. Entering through .......

4.3 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo 2 bedrooms / 2 bathrooms Spacious Balcony overlooking Northern Siesta Key Sixth Floor Condo overlooks Northern Siesta Key Fully equipped Kitchen with seating for 4 at the dining table Beach Supplies include- Beach Cart, Chairs, Umbrella, Cooler, Raft/Flo.......

4.5 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Sixth Floor Condo with balcony overlooks Southern Siesta Key * Fully equipped Kitchen with seating for 4 at the dining table and 4 at kitchen island * Beach Supplies include- Chairs, Umbrella, Cooler, Raft/Float Items, Beac.......

4.7 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Spacious Balcony overlooking Southern Siesta Key * Third Floor Condo overlooks the canal and Southern Siesta Key * Fully equipped Kitchen with seating for 4 at the dining table * Beach Supplies include- Chairs, Umbrella, Co.......

5.0 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo 2 bedrooms / 2 bathrooms Spacious Balcony overlooking Northern Siesta Key Second Floor Condo in the peaceful treetops Fully equipped Kitchen with seating for 6 at the dining table Beach Supplies include- Chairs, Cooler, Raft/Float Items, Beach Towels Com.......

4.8 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo 2 bedrooms / 2 bathrooms Spacious Balcony overlooking Intracoastal Waterway Second Floor Condo in the peaceful treetops Fully equipped Kitchen with seating for 6 at the dining table Beach Supplies include- Chairs, Cooler, Raft/Float Items, Beach Towels C.......

4.9 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo - Corner Unit 2 bedrooms / 2 bathrooms Spacious Balcony overlooking Southern and Western Siesta Key Third Floor Condo overlooks the canal and Gulf of Mexico Fully equipped Kitchen with seating for 4 at the dining table Beach Supplies include- Chairs, Umb.......

4.5 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 3 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 3 bedrooms / 2 bathrooms * Sleeps up to 8 * Spacious Balcony overlooking Northern Siesta Key * Third Floor Condo above the treetops * Fully equipped Kitchen with seating for 6 at the dining table * Beach Supplies include- Chairs, Umbrella, Cooler, Ra.......

5.0 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Spacious Balcony overlooking Southern Siesta Key * Fourth Floor Condo overlooks the Intracoastal Waterway and Southern Siesta Key * Fully equipped Kitchen with seating for 6 at the dining table * Beach Supplies include- Bea.......

3.9 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Spacious Balcony overlooking Southern Siesta Key * Fifth Floor Condo overlooks the canal and Southern Siesta Key * Fully equipped Kitchen with seating for 4 at the dining table * Beach Supplies include- Beach Cart, Chairs, .......

4.6 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Sixth Floor Condo with balcony overlooks Southern Siesta Key * Fully equipped Kitchen with seating for 4 at the dining table * Beach Supplies include- Chairs, Beach Cart, Umbrella, Cooler, Raft/Float Items, Beach Towels * Com.......

4.8 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 3 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * RARE! 3 bedrooms / 2.5 bathrooms * Sixth Floor Condo with balcony overlooks Northern Siesta Key with views of the Gulf of Mexico * Fully equipped Kitchen with seating for 8 at the dining table * Pool Table In Living Room * Beach Supplies include- Cha.......

4.9 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Seventh Floor Condo with balcony overlooks Southern Siesta Key * Fully equipped Kitchen with seating for 4 at the dining table * Beach Supplies include- Chairs, Beach Cart, Umbrella, Cooler, Beach Towels * Community Saltwat.......

4.7 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Seventh Floor Condo with balcony overlooks South-Eastern Siesta Key * Fully equipped Kitchen with seating for 6 at the dining table * Beach Supplies include- 4 Chairs, Umbrella, Raft/Float Items, Beach Towels * Community Pool.......

4.8 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Ninth Floor Condo with balcony overlooks North-Western Siesta Key- Gulf Views! * Fully equipped Kitchen with seating for 4 at the dining table * Beach Supplies include- 2 Chairs, Beach Towels * Community Pool- Largest pool on.......

4.8 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Spacious Balcony overlooking Southern Siesta Key * Top Floor Condo with amazing views, including the Gulf of America from the balcony * Community Pool- Largest pool on the Key! * Pickleball & Tennis Courts * Gated Community.......

4.9 Star Review

The Anchorage Resort on Siesta Key - includes resort amenity access! Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer. * Anchorage Resort Condo * 2 bedrooms / 2 bathrooms * Eighth Floor Condo with balcony overlooks South-Western Siesta Key * Fully equipped Kitchen with seating for 4 at the dining table * Beach Supplies include- 2 Chairs, Beach Cart, 2 Boogie Boards, Pool Noodles and toys, Beac.......

4.5 Star Review

Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 3rd floor condo in the very desirable island community of Bay Oaks. Bay Oaks offers a heated pool, barbecue grill area, tennis courts, fishing area on the intra-coastal and pool table in the club house. Vacation on beautiful Siesta Key less than a ten-minute walk to the public beach access with provided beach chairs, towels, and cooler... everything you need to enjoy the pristine beach across the street. Located 1/2 mile from.......

4.8 Star Review

Welcome to Siesta Beach House Unit #105, your beachside vacation condo that has now been fully renovated in preparation for accommodating you!! The Siesta Beach House community has direct beach access, community heated pool, 1/4 mile from Siesta Key Public Beach with tennis courts, picnic pavilions, and playground. Siesta Key has become popular for its soft white sand beaches and island life. Utilize any one of the many free ride (tips only) services on the island or the free island shuttle to v.......

4.8 Star Review

Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 2nd Floor condo in the very desirable island community of Bay Oaks. Bay Oaks offers a heated pool, barbecue grill area, tennis courts, fishing area on the intra-coastal and pool table in the club house. Vacation on beautiful Siesta Key less than a ten-minute walk to the public beach access with provided beach chairs, towels, and cooler... everything you need to enjoy the pristine beach across the street. Located 1/2 mile from.......

4.8 Star Review