Holiday rentals in Siesta Key

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want! Please message me if bringing 2+ pets

Spectacular Siesta Key Beachfront Condo

Welcome to the Siesta Key! Relax and enjoy the fine, pristine white sand! The spacious unit T0302 sits at the center of Siesta Key Beach. Our private beach is steps away and maintained by our staff daily. The unit is ~1500 square feet and fully furnished for up to 6 guests. Guests can enjoy the beach view from the lanai/balcony. Linens and towels are included. WIFI, covered parking for 2 cars, beach chairs are complimentary. Our club features 2 pools, 3 tennis and 4 pickle ball courts.

Near beach. Pool view. King bed. Daily rentals

The ‘pool view’ overlooks the swimming pool & has a private covered open porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a Smart TV. Separate bedroom with King size bed 3 mins walk to Crescent beach access #12 You can walk to a great choice of places to eat and drink Max 2 guests No smoking, No Pets, Great Location, Good Value.

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Ringling Bungalow features a bright and airy one bedroom space; with a kitchen, bathroom, and a private deck overlooking Heron Lagoon. With a king-size bed you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. The sofa turns into a queen size bed, allowing for a max occupancy of three.

Siesta Beach penthouse w/ Gulf side pool & access!

Luxurious beachfront living with wrap around deck, gulf views and a wet bar with beverage fridge! On 2nd floor of an elevated building which gives you optimal views for sunsets. This is a rare private, quiet 6-unit condo complex located steps to town. Just under 1500 sf condo w/ vaulted, beamed ceilings, fireplace, gourmet kitchen, bar, master suite, spa bathrooms, ocean front balconies and heated pool. Walking distance to town , 25 min to SRQ and 1hour 15 min to RSW and TPA.

Beach, Village, Dock & Private Pool! One-of-a-kind

Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.

Beach N Bay 206 by Duncan Real Estate

Welcome to Beach N Bay 206! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is the island vacation cottage duplex that's so tropical and fun, you'll swear you can hear steel drums!

Latitude Adjustment | Waterfront, Walk to Beach!

🦩Exclusive Amenities Include: • Private Heated Pool • Waterfront Views on 2nd & 3rd Story Balconies • 8 Minute Walk to Siesta Key Village • 2 Minute Walk to Siesta Key Beach • 4 Bedrooms (2 Master Bedrooms), 3.5 Baths • 2 King Beds, 1 Queen Bed, 2 Full Beds (Sleeps 10) • 2 Balconies With Seating • Private 2 Car Garage • 2 Kayaks • Gas Grill • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transportation Available

Canal Upper-Gorgeous 3 bed 3 bath near SK Village

Canal Upper is just minutes away from Siesta Key Beach, voted the # 1 beach in the U.S! The kitchen features stainless steel appliances and a dining room table that fits up to 6. Beach carts, chairs & towels are provided for the 5-6 block walk to Beach Access #5. Step outside & you’ll find a quaint outdoor area featuring a tranquil pool, hot tub, and BBQ: perfect for family gatherings!

2BR Penthouse - Stunning Beach Views on Siesta Key

The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished 2-bedroom, 2-bathroom condo is the perfect getaway for anyone looking to enjoy the beauty of the Gulf Coast.