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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Siesta Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale - Renovated
Siesta Key Condo
- 
4.9 Star Review
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL
Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could th.......read more
2 Bedroom(s)
Sleeps 6
Condo
Luxurious Waterfront Retreat minutes from Beach, bay front with city views.
Siesta Key Private vacation home
- 5.0 Star Review
Villa Siesta sits poetically in a walled, gated garden on deep, azure-colored Hansen Bayou with views of Sarasota Bay & City skyline. This architecturally unique 5400 sf villa is built around a spacious tower with winding 3 story staircase opening to each living level.
The romantic residence is located just a few blocks from Shell Beach, les.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Siesta Key Condo
- 5.0 Star Review
Location, Location, Location!
Located steps from the Gulf of Mexico, on the best part of the famous Crescent Beach. Our home offers beautiful full gulf views.
Welcome to our spacious, fully equipped condominium, minutes from great shopping, restaurants, and more! Recently remodeled kitchen. Many recent updates. Enjoy this beautiful, well-ma.......read more
2 Bedroom(s)
Sleeps 4
Condo
Firethorn 611 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Pool...
Siesta Key Condo
- 5.0 Star Review
Welcome to this newly remodeled 6 person, 2-bedroom, 2-bath ground floor unit on Bay Side with a lovely canal view! Enjoy a roomy kitchen which provides plenty of countertop and cooking space, along with all new cabinets and dining ware. Full second bathroom with a walk-in tile shower. New vinyl flooring and bright walls along with an extended livi.......read more
2 Bedroom(s)
Sleeps 6
Condo
Luxury on Crescent Beach - Great Location!
Siesta Key Condo
- 4.8 Star Review
Luxury condominium directly on world-famous Crescent Beach! Located at Siesta Breakers - one of the premier properties on Siesta Key. Enjoy this designer furnished unit - with quality flooring, cabinets, granite counter tops, kitchen appliances, two televisions, free wi-fi, and classic island-inspired furnishings. The property features a beautiful.......read more
2 Bedroom(s)
Sleeps 4
Condo
Walk To Siesta Village And Beach/Private Pool & Hot Tub
Siesta Key Apartment
- 4.9 Star Review
Private 2 bedroom 1 bath apartment in large house for rent. The apartment is actually the main portion of the house and the other portion of house is rented to annual tenant with no access to pool. Couch in living room can be used to sleep an additional person. King bed in master and queen bed in second bedroom. All high end appliances, large scre.......read more
2 Bedroom(s)
Sleeps 5
Apartment
BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED
Siesta Key Condo
- 4.9 Star Review
Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL
Top beachfront unit at Fisherman's Cove!! Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the.......read more
3 Bedroom(s)
Sleeps 8
Condo
Ground Floor at Bay Oaks in Siesta Key - Watch Dolphin in the Bay - Fish from the Pier. Unit E81
Siesta Key Condo
- 3.9 Star Review
Relax in Style at Bay Oaks in Siesta Key - Watch Dolphin in the Bay, Fish from the Pier!
Nicely furnished ground floor condo located in the popular Bay Oaks resort on Siesta Key. Covered parking just steps from the unit. Living room has comfortable leather seating, with a queen sleeper sofa for additional sleeping. Both bedrooms have en-suit.......read more
2 Bedroom(s)
Sleeps 6
Condo
Sprinkle of Irish charm, beautifully updated, Siesta Dunes 8-205
Siesta Key Condo
- 4.5 Star Review
Welcome to our condo 8/205. Featuring beautiful wood floors, Siesta Dunes Beach 205 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it’s easy on the wallet while its lovely atmosphere makes it a great home to return to for relaxing e.......read more
2 Bedroom(s)
Sleeps 6
Condo
1st Floor Gulf View, Convenient Walk Out to Pool w/ 3 Porches!
Siesta Key Condo
- 5.0 Star Review
Enjoy your beachfront vacation condo here in Siesta Key, with perfect sandy beaches right out your door. Siesta Key is a barrier island along the southwestern coast of Florida and is considered by beach experts to be one of the most beautiful beaches in Florida. When you stay with us at Siesta Dunes Condominiums, you stay in style and comfort, just.......read more
2 Bedroom(s)
Sleeps 5
Condo
Stunning 3 Bedroom Home with Roof-Top Pool on Siesta Key!
Siesta Key Apartment
- 5.0 Star Review
SIESTA KEY BEACH RESIDENCE: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 1st floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 9 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 .......read more
3 Bedroom(s)
Sleeps 9
Apartment
Stunning 3 bed/ 2.5 bath Townhouse Steps From Siesta Key Beach!
Siesta Key Private vacation home
Featuring high ceilings and a spacious living area this 3-bedroom, 2.5-bath, beautifully renovated townhouse condominium presents the best Siesta Key has to experience. This multifloored unit offers the convenience of condominium living without a high-rise building. One of four townhomes in the Beach Walk complex, this home features lush tropical l.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Beautiful 2Bed/2Bath at Crystal Sands, Steps from Pool and Siesta Key Beach!!
Siesta Key Condo
- 4.3 Star Review
Just 300 feet of powder white sand separate this unit from the crystal blue waters of the Gulf of Mexico! This FULLY RENOVATED, 2-bedroom 2-bathroom unit offers sleeping accommodations for 6. Inside, you will find a chef's kitchen with plenty of space to cook while being open to entertain guests as well. Relax on one of your two private outdoor bal.......read more
2 Bedroom(s)
Sleeps 6
Condo
Beautiful 3 Bed/2.5 bath With Roof Top Pool on Siesta Key!
Siesta Key Apartment
- 5.0 Star Review
SIESTA KEY BEACH RESIDENCE: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 9 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 .......read more
3 Bedroom(s)
Sleeps 9
Apartment
Prime Location! 200 feet to the beach. 2 blocks to shopping and restaurants
Siesta Key Private vacation home
- 4.9 Star Review
We are excited to have you! Heron's Haven is located 200 feet from an entrance to Siesta Key beach which is rated the #1 Beach in the USA. This private home boasts all the amenities you will need while on vacation and is within the desired "Golden Triangle" on the island. Short walk (two blocks) to shopping, dining, bars and much more. The front po.......read more
2 Bedroom(s)
Sleeps 6
Private vacation home
NEW! Luxury 4/3 Home on Siesta Key w. Heated Pool & Water View!
Siesta Key Private vacation home
Enjoy your stay in this beautiful 4 bedroom, 3 bathroom newly built home across 2,292 sq ft on Siesta Key in the gated community “La Linda Siesta Key Estates”.
** residence under construction, you may be inconvenienced during the week - Summer 2023 **
As you enter through the main door, you will be welcomed by a luminous open floor plan a.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Modern 3 Bed/2.5 bath Gulf Side Condo Steps from Siesta Key Village and Beach!!
Siesta Key Condo
- 5.0 Star Review
This updated, relaxing, modern, beachfront condo, offers partial beach views and a straight walk to the sugary white sand and crystal-clear water! With 3 bedrooms, 2.5 bathrooms, this home comfortably sleeps 8. Wake in the master bedroom’s king size bed to enjoy the Gulf of Mexico views from your own private balcony. In the second bedroom, is a que.......read more
3 Bedroom(s)
Sleeps 8
Condo
Updated Top Floor Siesta Key Vacation Rental at Bay Oaks
Siesta Key Condo
- 3.7 Star Review
Recently fully renovated and tastefully decorated 2-bedroom 2-bathroom 5th Floor Penthouse condo in the very desirable island community of Bay Oaks. Bay Oaks offers a heated pool, barbecue grill area, tennis courts, fishing area on the intra-coastal and pool table in the club house. Vacation on beautiful Siesta Key less than a ten-minute walk to th.......read more
2 Bedroom(s)
Sleeps 5
Condo
Beautifully Updated Ground Floor at Gulf & Bay Club. Gulf Front Living at it's Finest!
Siesta Key Condo
- 5.0 Star Review
Beautifully Updated Ground Floor Condo at the Desirable Gulf & Bay Club. Gulf Front Living at it's Finest!
Just steps from Crescent Beach, you are sure to fall in love with this beautiful, spacious 2 bedroom, 2 bath ground floor unit with all the amenities the Gulf & Bay Club Resort has to offer. Step out the door of the enclosed lanai and .......read more
2 Bedroom(s)
Sleeps 8
Condo
Bay Oaks, End Unit, Walk to Beach, WiFi, Updated, Pool, Tennis, Complex Fishing Pier
Siesta Key Condo
- 4.8 Star Review
New Listing in Bay Oaks!!! Fabulous 3rd floor condo in popular Bay Oaks on the BAY ((elevator bldg.) close to Siesta Key public beach as well as Crescent Beach. Plan your beach vacation with us today!! Feel at home in our 2 bedroom, two bath condo with all the complex amenities you could ask for all wrapped up in a relaxing atmosphere. Nearby .......read more
2 Bedroom(s)
Sleeps 5
Condo
New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104
Siesta Key Condo
- 4.0 Star Review
This ground floor 2 bedroom, 2 bathroom unit is nicely updated and comfortably furnished with easy access to the pool and the beach. Our Property is managed by the Siesta Dunes Rental Office and the staff is available to assist you during your stay.
Amenities include:
Gulf View, from 1st Floor
King in Master Bedroom
Show.......read more
2 Bedroom(s)
Sleeps 4
Condo
Perfect Siesta Village Pool Home! Walk to the beach and hang out in the Village!
Siesta Key Private vacation home
- 4.8 Star Review
**The property is a monthly rental, but please check with us for availability, as we can accommodate shorter stays if the rest of the month is not booked**
This lovely, fully updated CANAL front pool home is a 3-bedroom, 3-bathroom property that sleeps six. Located on a quiet cul-de-sac just one block from the Siesta Key Village and the best bea.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Cozy Siesta Key studio 5 minute walk to Village
Siesta Key Condo
- 5.0 Star Review
Summary:
Keep it simple at this peaceful and centrally-located
Humble 450 sq.ft. space with bed, sofa bed, large TV, full kitchen, full bathroom. Huge outdoor courtyard.
The Space:
null.
The Neighborhood:
Quiet, serene, almost always sunny. Neighbors out walking their dogs daily.
Getting Around:
A car is recomme.......read more
Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach
Siesta Key Condo
- 4.9 Star Review
HERE'S 23 TOP REASONS why This Condo Unit is the Perfect Place to Stay for Your Siesta Key Vacation. Also, read below about our new exclusive rain policy.
1. Unbelievable breathtaking beach views! Take the elevator to the 3rd floor. Open the door to our unit 304. Experience an unforgettable 3rd floor vantage point view offering 180 degre.......read more
Studio
Sleeps 4
Condo
Prem 2Bed/2Bath Gate House Cottage with private beach access!
Siesta Key Cottage
- 4.8 Star Review
Wonderful stand alone cottage ready for your perfect retreat! Master bedroom has a king size bed, full private bathroom, walk in closet, flat screen TV and attached access to the secluded rear yard. Second bedroom has two twin beds with large closet. The large open floor plan has a living room with a couch, love seat and flat screen TV. The un.......read more
2 Bedroom(s)
Sleeps 4
Cottage
3 bedroom house+ Private pool + huge yard. 12min walk to beach. Pet friendly.
Siesta Key Private vacation home
- 4.9 Star Review
Enjoy this private pet friendly house with your own swimming pool, in beautiful Siesta Key. Oversized private lot. Renovated main bathroom and master bathroom. Custom designed high end rain showers. ** HEATED POOL ** Walk to Crescent Beach or beach access 10 - Walk to the North Village or ride bikes. This well maintained vacation home comes fully.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Bay, Pool, Tennis Court Views, 2 Master Suites, Stainless Kitchen, Tile Floors, 3 TV's
Siesta Key Condo
- 4.8 Star Review
Harbor Towers sits directly on the bay where you can enjoy morning sunrises. This is a premier property with all the amenities you could want or need and located conveniently on Siesta Key close to famous Siesta Key beach! Fabulous powdery white sands of Siesta Key Beach are just a short bike ride or Trolley ride away.
Window project expecte.......read more
2 Bedroom(s)
Sleeps 6
Condo
NEWLY REMODELED! On World Famous Crescent Beach
Siesta Key Condo
- 4.8 Star Review
Condo was fully remodeled in the summer of 2020 complete with beautiful new flooring. Kitchen was completely redone with new cabinets, quartz countertops, and all Stainless Steel appliances.
TV's in both bedrooms
Two new Recliners in Living Room
55" HD LED TV with DVR and Blu-ray Player in LR
King bed in Master B.......read more
2 Bedroom(s)
Sleeps 6
Condo
Stunning Siesta Key Beach Views from 2 Bedroom Condo!!
Siesta Key Condo
Stunning Updated Condo with Spectacular Siesta Key Beach Views! Our House At The Beach! Enjoy panoramic views of the Gulf of Mexico & Siesta Key Beach, to fantastic sunsets & downtown Sarasota, all from 12 floor-to-ceiling sliding doors that open onto 2 huge balconies. Full gulf facing corner unit on the 6th floor, accessible by stairs or elevator,.......read more
2 Bedroom(s)
Sleeps 6
Condo
Spacious 3 Bedroom Gulf Side Townhome with Rooftop Sun Deck On Siesta Key!!
Siesta Key Private vacation home
- 2.5 Star Review
Welcome to Surfside! Where you will experience beautiful Siesta Key Living! This 3-Bedroom, 2.5-bathroom home sleeps up to 6. Relax on the spacious rooftop sun deck and take in the amazing sweeping views of our world-famous beach, Siesta Key. Inside, on the first living level, you will find a large, open living area, a half bathroom, a nice sized b.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Find Affordable Siesta Key Beach Hotels & Vacation Rentals
Plan your Siesta Key Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Siesta Key, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.
Vacation Rentals Nearby Tampa Bay Destinations
Find nearby vacation rentals and some of the Best Hotels with cheap rates in Siesta Key, FL for you visit to the area, all a short drive to Siesta Key, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.
Rentals in Siesta Key, FL
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