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!

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Showing Results 1 - 15 of 25
Name
Area
Description
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. 
1350 N. Portofino Drive #309
Area: Siesta Key
You will love this updated 3rd floor turnkey furnished unit with gorgeous Intracoastal and Harbor views. Siesta Harbor is surrounded by the Intracoastal Waterway with a boat harbor and deeded boat slips which can be leased for a nominal fee. This 55+ community is ideal for your May through December 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. No smoking and no pets please.
1257 Tree Bay Lane
Area: Siesta Key
Expansive four bedroom home on the water on South Siesta Key is available for season 2017. Through the entrance on the first floor you enter into the family room with views of the pool and intracoastal waterway. There is also a bedroom and private bathroom on this level. Up the open staircase leads to the main living floor with a skylight over the open plan kitchen, dining room and living room. All of these rooms overlook the pool and the intracoastal waterway. The master bedroom also has a comfortable sitting area and also a water view, the master bathroom features a large tub and separate shower, with double sinks. All bathrooms have been recently updated, and the bed sizes in all the remaining bedrooms are queen sized. The house also has 2 sofa beds, perfect for extra guests. There is a dock at the house and the beach access is a short distance. Available for Season. SINGLE FAMILY HOME SIESTA KEY SARASOTA FLORIDA SEASONAL RENTAL
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.
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.

5880 Midnight Pass Road #508
Area: Siesta Key
Enjoy the beautiful sunset from this 5th floor condo. This 2 bedroom 2 bath condo has been freshly painted and all new furniture. The condo is located on the Gulf side of Siesta Key. This community has private pool, tennis court and small fitness room. Walk through the beautiful court yard to your own beach. You can take a leisurely walk to the public beach as well as take the free taxi rides to Siesta Key Village for the nightly dining and music. Unit is available for season 2018.
1208 Solitude Lane
Area: Siesta Key
Fabulous Siesta Key House available for season or long term near the best beach in the World! Raised home with lots of parking beneath, step into this open plan living/dining room and kitchen with volume ceilings and beautiful wood floors. The spiral stair case leads up to a loft overlooking the living room, use this for extra space. The house is split plan with a spacious master bedroom and bathroom. The two bedrooms and den/office are at the other end of the house. Bright with lots of windows and natural light, coastal decorating to get you in the mood for a fabulous stay. AVAILABLE IMMEDIATELY.
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.
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.
5790 Midnight Pass Rd. #110A
Area: Siesta Key

This 2/2 Gulf & Bay ground floor unit allows you beach and pool access just outside your lanai door. This is the ultimate in casual Florida living, steps to the sugary sands of Siesta Key beach. This gated resort offers all the amenities for a fabulous vacation rental including state of the art fitness center, playground, ponds for fishing, pools, tennis courts, and shuffle board. The unit also includes a laundry room with full size washer/ dryer and a reserved carport space at your front door. . February and March are always owner occupied.

5525 Azure Way
Area: Siesta Key
Fabulous large home decorated to perfection just over 400 steps from Siesta Public Beach, one the of the best beaches in the world. House is large and has 5 en suite bedrooms. Enormous pool with lions head fountains and hot tub overlooking the wide canal. You can tie your boat up to the sea wall, and enjoy the outdoor eating area by a man made beach overlooking the canal. All the comforts of home for large family gatherings. House has two master suites one on the ground floor and second one upstairs. Beautiful landscaping in this fabulous Siesta Key home, convenient to the Siesta tennis courts and the village. Rentals of six months or less are subject to local and state taxes.
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. 
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.
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.
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.

Showing Results 1 - 15 of 25
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