Townhome holiday rentals in Siesta Key

Summer Discounts Available! Steps from the Beach!

Welcome to Your Dream Beach Getaway! Steps (one block!) from the sugar-white sands of Holmes Beach. We provide bikes, paddle boards, and all the other beach gear you will need for fun in the sun! Nestled in a quiet beachside community on the famed Anna Maria Island, this newly renovated home is ready for your dream vacation! Enjoy the shared HEATED pool or stroll to shops, restaurants, and the vibrant attractions of Anna Maria Island— a quick bike or trolley ride away. Perfect for families!

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse

Kick back and relax in this calm, stylish space. In Cedars East, across from beach AND on the bay. Sleeps 6 - california king master & double bed upstairs. All new carpets upstairs and full laundry in the unit too! Lovely enclosed balcony overlooking trees and boardwalk. Couple of trek bikes available - 10 min walk/ 3 min cycle to beach. Large shared swimming pool, tiki bar, fitness center, tennis on site. Jetty, boardwalk & walk paths. Excellent location, pets allowed. RRR-00819. 2023

Still Waters Townhome, Sunrise and Sunset Views

Elegant home with 4 balconies, 2 overlooking water. Sunset and sunrise views. Gourmet kitchen, granite countertops, cooktop range, stainless steel appliances. Coffee maker, tea kettle, Nutra-bullet, toaster and more. Each room has a large flat screen smart TV. Bright, modern, immaculate. Wireless internet, Ethernet and Netflix. Washer and dryer on main level. Five minute walk to white sand private beach, complimentary umbrella and chairs. No smoking, no pets, no events.

Great Times & Tan Lines

Make memories in your gorgeous waterfront townhome with 2 bedrooms and 1 ½ baths. An intimate community with 20 units ideally located 3 miles from the laid-back beach life of Anna Maria Island or 4 miles from the energy of downtown Bradenton and Manatee Riverwalk. Walk to Palma Sola Causeway Park and boat ramp where you rent paddle boards, jet skis, kayaks, plus horseback riding in the water. Relax at home, fish off the dock or watch for visiting manatees and stingrays.

Luxurious 3BR townhome Little Harbor Resort w/view

Luxury 3 Bedroom, 2.5 Bath, End Unit Townhouse in Little Harbor Resort & Club, Ruskin, Florida. Sleeps 6 comfortably. We are taking all COVID-19 precautions including additional cleaning upon check out and additional days between reservations. The resort is set on tropical grounds overlooking Tampa Bay featuring two outdoor pools, sports court, shuffleboard, volleyball, water sports rentals, a marina and on-site restaurants (a bay-view restaurant, a poolside bar).

Huge heated pool| Walk to shops| 30 min to beach

Welcome to your vacation home! • 2 queen and 1 king size beds • Each bedroom has smart TV and bathroom • High chair and pack-n-play • Stunning lake view from screened lanai • 5 min walk to shops and restaurants nearby • 25 minutes to most stunning Florida beaches (beach chairs included) • Plus our gated secured community includes heated pool, playground, tennis, basketball, and volleyball courts. Start your perfect vacation today! Absolutely no smoking!

CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available. MAX Occupancy 4 people including children of any age.

Updated Townhome, Secluded Beach + Pool

Renovation completed in 2025! New master bath, whole house repaint, new furniture, etc. Longboat Key beach is ok post-hurricane, stores and restaurants open! Private updated townhome, just 100 yards from the beach. The spacious 2BR/2.5BA new listing has been tastefully furnished. It is within the exclusive community of Cedars East which offers a pool, fitness center, tennis, kayak/paddleboard launch and private fishing pier.

Reel Paradise

Escape to your own island paradise on world-famous Siesta Key! This 3 bedroom/3 bath townhouse is perfectly located on the Grand Canal plus just one block to beautiful, Siesta Key Beach with its powdery white, quartz sand & turquoise waters as well as strolling distance to the iconic Siesta Village filled with restaurants, live music, & shopping. It’s the perfect trifecta!