Siesta Key Vacation Rentals

We have vacation rentals along Siesta Key with sunny beaches on the gorgeous Gulf of Mexico with picturesque sunsets and world renowned crystal-white, powdery sand that stretch for miles. Siesta Key is a barrier island off of the central western coast of Florida . It is situated between Sarasota Bay and the Gulf of Mexico. There are shops from the chic and elegant to the hip and funky, with all sorts of fashion, beach accessories and souvenirs. Siesta Key offers restaurants where you can go to grab a quick breakfast or lunch in your flip-flops or to relax in style over an extraordinary dinner. The Siesta Key vacation rentals here are luxurious. The Siesta Key Beach is voted #1 Beach year after year!

TOUR SIESTA KEY!

Tour Siesta Harbor on Siesta Key


Showing Results 1 - 15 of 25
Name
Area
Description
19 Whispering Sands Dr. #805
Area: Siesta Key

Enjoy this great view of the gulf from this 2 bedroom, 2 bath condo on the 8th floor. Condo has been remodel with granite kitchen counter tops, built in cabinets in master bathroom and tile floor. You can walk out of the building directly to your own private beach. This unit is walking distance to the Siesta Key village, where you can enjoy your morning coffee and a great meal at one of the local restaurants. Sit on your lanai and enjoy a beautiful sunset.

1350 N. Portofino Drive #303
Area: Siesta Key
Siesta Harbor is surrounded by the Intracoastal Waterway with boat harbor and deeded boat slips. Boat slips can be leased for a nominal fee. This 55+ community is ideal for your winter vacation with easy access on and off Siesta Key. Just a 1/4 mile from the Stickney Point bridge, shopping and restaurants are within easy walking distance. Beach access is directly across the street. Siesta Harbor offers a community pool and spa, numerous activities, including a fishing club and social events in the clubhouse. You will love this updated 2 bedroom unit with gorgeous harbor views.
156 Siesta Drive
Area: Siesta Key
Unique FURNISHED home available for rent on Siesta Key. This single family home has four bedrooms, three bathrooms, living room, family room, kitchen with dining area, breakfast bar, two bedrooms on the second level loft, laundry room, spacious deck with two sitting areas, private pool and two car garage (ONLY one space available). The living space is on two levels with stairs to both and NO elevator. Master bedroom has a king sized bed, walk in closet, en suite bathroom with double sinks and a stall shower. Bedroom two and three have queen sized beds and bedroom four has two twin beds. First guest bathroom has a tub/shower combination and the second has a stall shower. Laundry room and third bathroom are on the garage level all other living areas on the second and third levels. Home is available for an annual or short term rental. Short term rentals must be month long or longer. Small pet allowed with the owner's approval. Available immediately.
5029 Oxford Drive
Area: Siesta Key
Nestled in beautiful Florida gardens with lush vegetation, impeccably maintained.  Through the large wooden gate to courtyard pool and private entrance to the house. Marble floors and luxurious furnishings abound in every room.  This house is on the Grand Canal, and boats docking is available.  Short distance from the village and pristine white sandy beaches. 
9393 Midnight Pass Road #502
Area: Siesta Key
Enjoy this bright 2 bedroom 2 bath condo on the 5th floor. You can sit on your lanai and enjoying your morning coffee and in the evening and watch the wildlife. The kitchen is updated and it allows for the open view of the inter coastal water way. Both bedrooms have king size beds. This is the place to stay if you like quite neighborhoods. Open for December 2016, January 2017 and February 2017
1257 S. Portofino Drive #105
Area: Siesta Key
Water views and peace and quiet are what you will enjoy in this charming 1 bedroom, 2 bath ground floor condo in this 55+ community. Located on a deep water boat channel, this newly decorated condo offers a renovated kitchen with granite countertops, 2 renovated bathrooms, one with tub/shower and the other a stand alone shower, an open dining/living area with all new furnishings throughout and water views from every room. The living room is comfortably furnished with ample seating for guests to enjoy the 50" flat screen TV. Free long distance calling provided anywhere in the continental US and Canada. Overnight company can be accommodated on the queen size sleeper sofa. King size bed in Master w/ walk in closet. This light and bright unit offers an enclosed sun room with screens to take in the ocean breezes. Watch for boaters, dolphins, jumping fish and water birds from the intercostal waterway that provide easy access to the Gulf of Mexico. Right outside the unit is a boat dock for vessels up to 30'. A designated covered parking spot next to the building makes for easy access. The facility includes a heated pool, shuffleboard, BBQ grills, spa, sauna and fitness room. A deeded walkway to the sugar sand of Crescent Beach at the #1 rated Siesta Key Beach on the Gulf of Mexico is just across the street. Free shuttles for only the cost of a tip are available to transport you to shops, restaurants and entertainment on the Island. This unit rents for a minimum of 30 days. No smoking or pets allowed.
1250 N. Portofino Drive #301
Area: Siesta Key
Siesta Harbor is a 55+ community overlooking Sarasota's Intracoastal Waterway. This south-facing end unit features two bedrooms and 2 baths with a King in the Master and twins in the guest bedroom. The community laundry room/storage room is next to the elevator. Cable, phone and Internet are included with the rental. Boat slips right outside your door are available for a nominal fee. Deeded beach access across the street. The community offers social events and card games for winter guests with full use of the clubhouse, sauna, fitness, heated pool & spa and shuffleboard court. Take a short walk to the south village for shopping and dining or hop on Jonny's free rides for a short trip to the public beach or Siesta Key Village for more entertainment and fun. Relax on your lanai with your morning coffee and watch the boats go in and out of the Harbor. No pets allowed.
1321 Dockside Place #122
Area: Siesta Key
Ground Floor unit, boat and water views from your Island Get A Way.  Harbour Towne Yacht offers, tennis, pool, spa, dock.  This condo is near Siesta Keys sugar sand beaches and crystal blue waters.  Spend and evening in our Siesta Key village for a little night life.
1321 Moonmist Drive
Area: Siesta Key
This spacious Siesta Key Condo is located in a small hide-away community that is walking distance to world famous sand beaches. Featuring two large bedrooms plus a bonus room / den, two full baths a private patio. The community has a heated pool, and a fishing pier on intercoastal waters. Also your own private garden is waiting for you to relax after a long day out in the sun. Unit is booked December 29th thru February  2018 there is a 1 month minimum rent. April through December the minimum rent is 2 weeks. Welcome to Paradise.
130 Island Circle
Area: Siesta Key
Located on Palm Island on Siesta Key, this whimsical 3 bedroom, 3 bath ranch home will amaze and delight your senses! The attention to detail and quality of finishes is second to none in this island home on Siesta Key's Grand Canal. The gorgeous tropical setting brings you to the entrance foyer with a 10 ft. tongue and groove ceiling overhead and the Saltillo Mexican tile under your feet. The cheerful and hand-painted kitchen & bathroom tiles are a must see.... Walk 3 blocks to Siesta Key Beach, the #1 beach in the USA, or take a stroll to the Village for shopping, fine dining and entertainment. Enjoy all the amenities of home in this beautifully renovated 'old style Florida' island home
1622 Stickney Point Road #202
Area: Siesta Key
View the intracoastal from your master bedroom porch having a rest on the reclining chairs. This second floor townhouse is in the perfect location for your stay in SARASOTA and a short distance from a world famous beach. Located by the Stickney Point Bridge this renovated and beautifully decorated townhouse is ready for short term stays of a minimum of one month. Up the stairs to the front door and step into this light filled home, all up to date decorating in neutral tones. There is a guest bathroom on the first floor and an extra single bed for overflow guests. Up to the bedroom level and you will find two bedrooms, the master has a king sized bed and the second bedroom features a queen sized bed. There are two porches for relaxing on, one off the living room and one off the master bedroom. There is a washer and dryer in the unit, and the resort style complex features two swimming pools, one overlooking the bay and tennis courts. SARASOTA, NEAR SIESTA KEY, RENTAL.
1257 S. Portofino Drive #107
Area: Siesta Key
This 55+ community is ideal for your winter vacation. Enjoy your morning coffee from the lanai over looking the intercostal. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. 
5519 Azure Way
Area: Siesta Key
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car!!! 2 King/2 bunk beds /daybed , queen sleeper and space galore.
8630 Midnight Pass Road #A507
Area: Siesta Key
This gorgeous, totally renovated 2-bedroom 2-bath condo boasts stunning full Gulf of Mexico views. Enjoy coffee each morning on your top floor lanai or relax with a glass of wine and sunsets each evening. Every inch of this spacious open plan luxury condo has been remodeled with high-end finishes including; beautifully tiled bathrooms, stainless steel kitchen appliances, granite counter tops and custom cabinetry. No home away from home detail has been overlooked. The property is steps to the secluded sandy Gulf beach and has a cabana for your individual use. Heated pool and intercostal-side dock (for fishing, paddle boarding or kayaking) add to the list of amenities. The property is walking distance to Turtle Beach restaurants and a short trolley ride (which stops in front of the property) to both of Siesta Key’s villages. The unit is available for season and off-season. Laundry facilities are conveniently located on the same floor.
1257 S. Portofino Drive #104
Area: Siesta Key
Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. An open kitchen and remodeled bathrooms are some of the perks in this waterfront unit. Sit on your lanai and watch the boats go by as you sip your morning coffee. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. This is a 55+ community which means one renter in the party must be over 55 years of age. No pets and no smoking please. 

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