Vacation Rentals in Siesta Key, Sarasota FL

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 comfort, luxury, and style along the way. This multi-level property provides seamless access to Siesta Key.......

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 master suite is furnished with King-size bed, 32" flat-screen LED TV, walk-in closet, and large tub.......

4.8 Star Review

3 Bedrooms - 2 Baths - Sleeps 6
Siesta Key Vacation Rental

Pet Friendly - Pets Allowed

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 steel appliances, wood cabinetry, and granite countertops, plus a breakfast bar overlooking the cozy l.......

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 to book this property is : 23.......

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 updated eat-in style kitchen equipped with stove, fridge, microwave, and dishwasher. The kitchen also .......

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 almost wall to wall sofa set across from a flat screen TV. Moving towards the rear of the unit you will .......

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 local shopping, dining, and nightlife, Beach Road puts you in the heart of the fun. Exterior Features.......

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-Bari checks every box on the list. Enjoy a Location You'll Love Making the most of your Siesta Key ad.......

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 offers up the space, style, and proximity to fun that everyone deserves to enjoy. Settle into the Best.......

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 pairs comfort with the quality and convenience you deserve. Embrace a Prime Location Maximizing the fun .......

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 on-suite master bathroom with Jacuzzi tub and 2-person shower. The second largest bedroom offers 2 qu.......

5.0 Star Review

4 Bedrooms - 3 Baths - Sleeps 10
Siesta Key Vacation Rental

Pet Friendly - Pets Allowed

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 inside as well! Interior Amenities Holiday House 1 is a wonderful retreat for those looking for a pl.......

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 stay that brings comfort, quality, and convenience into every aspect of your getaway, Holiday House .......

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 doors out to the spacious screened patio with lounge seating and table. The master bedroom with ensuite.......

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 bed and TV and has an ensuite bathroom. The guest bedroom is furnished with two twin-size beds and T.......

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 condo is located on the third floor of the Jamaica Royale resort style beach community. It is a very .......

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 visiting with family or friends, a stay here offers up the scenery and style that they crave. Interior Am.......

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 great restaurants and shops near Stickney Point Bridge. Whether you're in town with family or making t.......

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. This property is only a block from the beach, within walking distance of great shops and restaurants .......

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 streaming services—perfect for unwinding after a day in the sun. The fully equipped kitchen features a .......

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 morning before hitting the beaches. Siesta Heron Suites & Villas offers a swimming pool great for cooling.......

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 morning before hitting the beaches. Siesta Heron Suites & Villas offers a swimming pool great for cooling.......

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, enjoying a vacation that reflects the beauty of Florida in every way. A paver walkway leads to a p.......

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 spot to enjoy morning coffee or a sunset dinner. Open the door and walk inside where an open concept.......

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 fun when it's time to get out and explore. The home is less than a mile to Turtle Beach and only 3 .......

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, shops, and fun waiting in Siesta Key Village take only 4 miles to reach from the front door of Siesta .......

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 restaurant, shopping, and entertainment options. Siesta Key Public Beach, located just 1/2 mile from the com.......

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 (tips only) available on the island. Entering through the front door you will arrive in the living .......

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 the front door, the open concept floor plan of Cottage B harbors no secrets and as you step into the.......

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/Float Items, Beach Towels Community Pool- Largest pool on the Key! Gated Community Siesta Key Trolley- .......

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, Beach Towels * Community Pool- Largest pool on the Key! * Gated Community * Siesta Key Trolley- free pic.......

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, Cooler, Raft/Float Items, Beach Towels * Community Pool- Largest pool on the Key! * Gated Community * .......

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 Community Pool- Largest pool on the Key! Gated Community Siesta Key Trolley- free pickup in front of th.......

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 Community Pool- Largest pool on the Key! Gated Community Siesta Key Trolley- free pickup in front of .......

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, Umbrella, Raft/Float Items, Beach Towels Community Pool- Largest pool on the Key! Gated Community Siest.......

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, Raft/Float Items, Beach Towels * Community Pool- Largest pool on the Key! * Gated Community * Siesta K.......

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- Beach Cart, Chairs, Umbrella, Cooler, Raft/Float Items, Beach Towels * Community Pool- Largest pool on .......

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, Umbrella, Cooler, Raft/Float Items, Beach Towels * Community Pool- Largest pool on the Key! * Gated .......

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 * Community Pool- Largest pool on the Key! * Gated Community * Siesta Key Trolley- free pickup in front o.......

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- Chairs, Beach Cart, Umbrella, Cooler, Raft/Float Items, Beach Towels * Community Saltwater Pool- Larges.......

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 Saltwater Pool- Largest pool on the Key! * Gated Community * Siesta Key Trolley- free pickup in front of th.......

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- Largest pool on the Key! * Gated Community * Siesta Key Trolley- free pickup in front of the resor.......

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 the Key! * Gated Community * Siesta Key Trolley- free pickup in front of the resort entrance * Priv.......

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 * Siesta Key Trolley- free pickup in front of the resort entrance * Private Beach access to Crescen.......

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, Beach Towels * Community Pool- Largest pool on the Key! * Gated Community * Siesta Key Trolley- free pic.......

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 Siesta Key "South-end Village" with shopping, restaurants, and bars. If you are looking for even mo.......

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 visit Siesta Key Village and the expanding south village offering a great selection of restaurants, s.......

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 Siesta Key "South-end Village" with shopping, restaurants, and bars. If you are looking for even mo.......

4.8 Star Review

Welcome to Bay Oaks, your Siesta Key Condominium complex featuring spacious condos for you and your family to vacation right in the heart of the action and entertainment Siesta Key Florida has to offer. This community offers complimentary covered parking with your rental for one car, community swimming pool, and other amenities to make your stay a wonderful experience! This unit is a 2 Bedroom, 1 Bathroom condo located on the ground floor of building D. Ground floor access makes it easy to get to both for those young and old, with no stairs or elevator to have to use to access. The condo is ta.......

5.0 Star Review

Experience this beautifully renovated and landscaped private pool home on Siesta Key!! It's one of the few private pool homes on the gulf side, close to Siesta Key Village, truly like no other!! A stunning 3 bedroom, 4 bath pool home located just 200 steps to the soft quartz sands of Crescent Beach on Siesta Key! Renovated throughout with all new decor including furnishings, appliances, flooring with relaxing outdoor living including 2 tiki lounging spaces by the pool and a tiki dining space off the kitchen. This unique home offers a perfect blend of comfort and style, making it an ideal retre.......

5.0 Star Review

3 Bedrooms - 4 Baths - Sleeps 8
Siesta Key Vacation Rental

Pet Friendly - Pets Allowed

It's time to truly "Play Hooky" in Siesta Key! Your stay offers stunning beachfront views and fantastic amenities, making it the perfect escape you won't want to leave. Ready to truly get away from it all? Playing Hooky is your ideal retreat on the serene south end of Siesta Key, nestled within the fantastic Bay Tree Club community. This charming 2-bedroom, 2-bathroom condo offers spectacular views of the Gulf of America, showcasing those famous Siesta Key sunsets right from your balcony, which also overlooks the sparkling community pool. With convenient sliding doors, you can easily open up t.......

4.9 Star Review

You're being drawn to a place where you can get away from all the routines of life. You need time to yourself. Curl up with a good book or take a walk on the beach with no a schedule to come back to. This is the home you've been longing for. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely stroll from the vibrant Siesta Key Village (packed with shops, restaurants, and en.......

0.0 Star Review

Time for some beach therapy! Dog-friendly, tri-level townhome in a prime location, offering direct beach access and ample space with 3 bedrooms and 2.5 bathrooms. Just steps from the #1-rated beach and Siesta Key Village. Craving some beach therapy? Look no further than "Vitamin Sea," a stunning tri-level Spanish-style townhome perfectly situated in a prime beachfront location on Siesta Key Beach, Florida! This spacious townhome offers 3 inviting bedrooms and 2.5 bathrooms, providing ample comfort and privacy for your family or group to unwind and reconnect. Plus, we're dog-friendly, so your f.......

4.5 Star Review

3 Bedrooms - 2.5 Baths - Sleeps 6
Siesta Key Vacation Rental

Pet Friendly - Pets Allowed

It's 'tini time at this remodeled 2-bed, 2-bath saltwater pool home on a Siesta Key! Enjoy direct canal access for fishing, paddle boarding, and wildlife spotting. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout, from the brand-new kitchen to the spa-like bathrooms. You'll find a designated office space off the ki.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 4
Siesta Key Vacation Rental

Pet Friendly - Pets Allowed

This charming retreat boasts a private pool and spa, an open-concept layout with a nicely updated kitchen, and a secluded primary bedroom with an office space, and screened porch. Just a short stroll to Siesta Key's North Village and the beach! Escape to Pink Flamingo, a charming 3-bedroom, 2-bathroom dog-friendly house on Siesta Key, where Old Florida charm meets modern comfort. Nestled under a stunning Banyan tree, this delightful home offers a lush, private yard featuring your very own pool and spa (pool heat available for an extra fee!). Inside, discover a true Old Florida cottage feel wit.......

4.8 Star Review

3 Bedrooms - 2 Baths - Sleeps 6
Siesta Key Vacation Rental

Pet Friendly - Pets Allowed

Remodeled condo, steps from the beach, offers an unforgettable getaway. With stylish coastal decor, it features a workspace, 2 bedrooms with ensuite bathrooms, and a balcony. Enjoy beach access, a pool, and proximity to Siesta Key Villages! Indulge in the laid-back luxury of this beautifully remodeled condo at Crescent Arms, just steps from the pristine shores of Siesta Key Beach, named #1 in the USA! Recently updated with a new kitchen, bathrooms, and chic coastal decor, this vacation rental offers the perfect blend of comfort and style. Step out the door and sink your toes into the powdery w.......

4.9 Star Review

Updated canal-front pool home with a fully equipped kitchen, luxe primary bedroom (canal views, pool access), and private dock for boating/fishing. Walk/bike to vibrant Siesta Key Village. This home is your dream Siesta Key vacation come true! Are you ready to truly unwind under the majestic shade of a sprawling Banyan tree? Imagine starting your day with a peaceful kayak paddle directly from your backyard, exploring the tranquil canal waters. "Spectacular" barely begins to describe this meticulously updated, canal-front pool home, designed for ultimate relaxation and fun. Step inside and feel.......

4.8 Star Review

Let the waves hit your feet, and the sand be your seat. Leave your stress behind and spend time at this boho chic beach retreat! You will be staying in walking distance to the pool, beach and Siesta Key's South Village! Welcome to your boho chic beach retreat located near the famous Crescent Beach on Siesta Key! This charming 2-bedroom, 2-bathroom condo comfortably sleeps 5, offering everything you need for a relaxing getaway. You'll feel right at home with a fully equipped kitchen for preparing your favorite meals and a cozy living room perfect for movie nights. Step out onto your screened la.......

4.5 Star Review

Pack your bags, your destination is PARADISE! Enjoy luxury amenities and private beach access at this 2 bedroom, 2 bathroom beachfront condo! Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot to unwind. Step inside to discover a large kitchen, ideal for preparing meals and entertaining. The primary suite offers complete relaxation with a.......

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 * 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, Beach Towels * Community Saltwater Pool- Largest pool on the Key! * Gated Community * Siesta Key Trolley- free pickup in front of the .......

4.9 Star Review