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 Harbor on Siesta Key

Showing Results 1 - 15 of 31
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 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
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.

4660 Ocean Blvd. #B2
Area: Siesta Key
Sea Village is a beautifully landscaped residential community on 5 acres overlooking the blue-green waters of the Gulf of Mexico. Located on the 2nd floor, this 3 bedroom unit shows like a model! It is completely renovated with bamboo floors, granite counters, 42" cabinets and stainless steel appliances. The Master bedroom suite has a walk in closet and a stackable washer/dryer. This is a serene and quiet complex with 2 pools, a fishing pier and an outdoor fire pit. The carport is located in front of the unit and plenty of guest parking is available. Walking distance to Siesta Key Beach and the Village for shopping, dining and entertainment. Owner will rent off-season, annually or seasonally. No pets permitted.
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.
6285 Midnight Pass Road #107
Area: Siesta Key
Come and relax in this bright end unit condo. This 2 bedroom 2 bath condo has its own washer and dry. The master bath has just been completed updated. The complex has a community room and exercise room on bayside/game room/2 lighted tennis courts/pickle ball courts. Private beach access, heated swimming pools, saunas, spas, outdoor grills, showers and picnic areas. Enjoy your morning coffee on the lanai with partial view of intercostal. Condo available now till Dec 31, 2017 for two weekly rental or monthly. Owners uses condo in Season.
1257 S. Portofino Drive #105
Area: Siesta Key
Newly listed ground floor rental at Siesta Harbor on Siesta Key comes with a boat slip right outside your door. 1 bedroom/2 bath unit with gorgeous views of the Boat Harbor and the Intracoastal Waterway. Enjoy the many social events at the clubhouse or head to the beach across the street. Take a stroll to the shops and restaurants at the South Village or take a free hop on shuttle to Siesta Key Village for more fun and entertainment. Your reserved carport is just steps away from your front door. This is a 55+ community. Special pricing for 5 month bookings, December - April. 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.
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.
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. 
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.
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.
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.
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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