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 29
Name
Area
Description
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.
5663 Midnight Pass Road #407
Area: Siesta Key
Enjoy all that Siesta Key has to offer at White Sands Village across from world famous Siesta Key Beach! This two bedroom two bath unit is located on the ground floor with partial views of the Intracoastal and steps to the heated pool! Washer and Dryer in unit. Community heated pool at clubhouse. King beds in both bedrooms. Public tennis courts at the beach directly across the street. Assigned covered parking.
231 Garden Lane
Area: Siesta Key
SIESTA KEY TROPICAL PARADISE great FAMILY HOME Right by the beach. North Siesta Key near the north bridge for easy on-and-off island access. Elegance and functionality in this updated, gated, North Siesta Key estate just across the street from inviting Shell Beach on the Gulf of Mexico and set on a very private road. The sparkling pool and spa are absolutely perfect. Relax inside or out on the large, covered porch. The main floor features a grand entryway, a large open-concept living and dining room, a cook's kitchen featuring a breakfast bar with top-of-the-line appliances, a bedroom with adjoining office/den and an adjacent full bath. Two guest bedrooms with a Jack and Jill bath and a pool bath. Venture up the showpiece staircase and go right to the master suite or go left to an oversized bonus room or fourth bedroom. With nearly 4,300 square feet of living area, there is plenty of room for all to ENJOY THE SARASOTA LIFESTYLE FOR A WEEK OR LONGER STAY. Minutes to the Siesta Key BEACHES & Village with shopping, restaurants, and entertainment.
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
1232 Solitude Lane
Area: Siesta Key
Siesta Key luxury water front home ready for the 2016 season. NEW CONSTRUCTION. THIS 5 BEDROOM, 4 BATH FAMILY HOME ON A PRIVATE DEAD END ROAD MAKES THIS LOCATION A GREAT PLACE FOR THE FAMILY TO PLAY AND ENJOY THIS NEW HOME ON SAILBOAT WATER, WALK TO THE POWDER SANDY BEACH OF SIESTA AND VILLAGE. . THIS RELAXED LIVING HOME HAS LARGE BEDROOMS.......LARGE KITCHEN AND SEPARATE PANTRY, STORAGE CLOSET THAT CAN ALSO BE USED FOR A WINE CELLAR...CENTRAL VAC SYSTEM,CENTRAL ALARM, HEATED POOL WITH POOL BATH ...VIEWS.....BOATING IN YOUR BACKYARD....ELEVATOR...3 CAR GARAGE, OUTDOOR SHOWER NEW SEA WALL CAP, BEAUTIFUL LANDSCAPING WITH LED GROUND LIGHTING. THE MOMENT YOU ENTER THE HOME YOU WILL FEEL THE QUALITY CONSTRUCTION. A MUST SEE. THIS IS THE PERFECT WINTER GET-A-WAY!
4532 Ocean Blvd. #201
Area: Siesta Key
SIESTA TOWNHOUSE DIRECT GULF FRONT - Spectacular views of the Gulf of Mexico. This completely renovated TURN KEY FURNISHED two bedroom end unit town house is totally modernized and absolutely perfect. Available for your IN Season stay for three months or longer. Just a very short walk to Siesta Village and Beaches. This 20 unit complex is set back on Ocean Blvd. on a large private lot for complete privacy and quiet. Master Bedroom with a picture window overlooking Gulf of Mexico and on the first floor sit back and enjoy the water views of the dolphins. Private pier /dock for fishing or enjoying life on the Gulf.
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.
1250 N. Portofino Drive #107
Area: Siesta Key
This freshly painted 2 bedroom, 2 bath condo is conveniently located on the ground floor next to the club house and features new appliances, granite counter tops and ceramic flooring. The bedrooms are carpeted with a Queen size bed in the Master, a walk in closet plus a full wall length closet. The guest bedroom has 2 single beds that can be combined to make a King. Updated bathrooms include a guest bath with a tub/shower combination. This unit has flat screen TV's/DVD's, phone and WI-FI. The complex is surrounded by the Intracoastal Waterway with boat access to the Bay. Boat slips can be rented for a nominal fee. Enjoy your morning coffee on the large Lanai overlooking the boats in the Harbor. There is 1 assigned carport and ample visitor parking. Siesta Harbor has a large saltwater heated pool, spa, fitness center, outside grills and tables, shuffle board courts, boat docks, fishing pier, a large community room with kitchen facilities for parties and a small lending library and pool table to occupy your time on that rare non-sunshine day. Take a short stroll to Crescent Beach (Siesta Beach) rated #1 beach in America. Siesta Harbor has right of way passage to the beach directly across the street. Put your toes in the fine quartz sand that stays cool on your feet as you walk along the Gulf of Mexico. Jonny's beach carts and vans offer free rides to Turtle Beach or Siesta Village for shopping, dining and night life. (Donations accepted). Siesta Harbor is an over 55 community. No pets allowed.
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.

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.
1208 Solitude Lane
Area: Siesta Key
Fabulous Siesta Key House available for season 2017/2018 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.
106 Beach Road
Area: Siesta Key
South Beach Miami Style House right on Siesta Beach! Ultra luxurious rental available for annual or longer term seasonal rental. Available immediately! Just steps away from Siesta Key Village and all the amenities it has to offer. On every level of this open floor plan home are unlimited views of the incomparable sand on Siesta Key and the Gulf of Mexico. Set in a tropical paradise of palm trees and lush vegetation, modern design with pops of color. Professionally decorated with beautiful furnishings and immediate move in is available. This attached multi level home has an elevator and under building parking. Step into the foyer and glass enclosed stair well plus elevator, the kitchen and family/dining open plan floor has a large porch overlooking the beach, as well as a bonus study/den. The kitchen features high end stainless appliances, large bar perfect for entertaining all overlooking the beach. Up another floor to more bedrooms and a family/game room on the top floor. This location is central on Siesta Key just a block or so from all that Siesta Key has to offer, perfect beach living!
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.
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.
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.

Showing Results 1 - 15 of 29
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