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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.
2 bed 2 bath Siesta Key Condo, walk to beach
Siesta Key Condo
- 
5.0 Star Review
1st floor condo with 2 community pools, beautiful walking path and shoreline access to the bay. Its 3/4 mile or 12 minute walk to the white sands of Siesta Key beach which has consistently been rated one of the top 5 beaches in the United States. Hundreds of restaurants and grocery stores are within 10 minute drive........read more
2 Bedroom(s)
Sleeps 6
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)
Cottage
Clean and Perfectly Remodeled Townhome, Steps From the Private Beach
Siesta Key Private vacation home
- 4.8 Star Review
Impeccably Clean, the reviews speak for themselves!
Located at Siesta Beach House, 5950 Midnight Pass Road, this luxurious Beach Townhouse, is just steps to its private beach entrance. Totally renovated top to bottom. This 2 bedroom, 2.5 bath Townhome is amazing and the best unit in the complex. Well, 302 is a close tie but that\'s mine .......read more
2 Bedroom(s)
Sleeps 5
Private vacation home
Updated Top Floor Siesta Key Vacation Rental at Bay Oaks
Siesta Key Condo
Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 5th Floor 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 the public b.......read more
2 Bedroom(s)
Sleeps 5
Condo
Siesta Key Beach Front Condo! Breathtaking view!
Siesta Key Condo
- 4.9 Star Review
This beautiful 2 bedroom, 2 full bath condo sleeps 6 and is located directly on one of the TOP 10 BEACHES IN THE WORLD!
Siesta Key has been a family favorite place for many years and once you stay here you will want to come back! Crescent Arms is a gated community and this unit is literally steps to the sugary white sand. It is in a gr.......read more
2 Bedroom(s)
Sleeps 6
Condo
Chinaberry 414 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Siesta Key Condo
- 5.0 Star Review
BEAUTIFUL & NEWLY RE-DECORATED 2 BED/2BATH; over 1400 s.f. located on the first floor. Ceramic tile floors in living areas. Dine al fresco or sip a margarita on the spacious screened lanai at the table or high top bar overlooking the lush tropical grounds, crystal white sands of the beach and aqua blue waters of the Gulf of Mexico. You are only ste.......read more
2 Bedroom(s)
Sleeps 6
Condo
101-Excelsior- Updated and Full Gulf Front!- 2 week minimum
Siesta Key Condo
- 4.8 Star Review
PERFECT PLACE TO WATCH THE SUNSET!! 2 bedroom/2 bath gulf front condo located on Crescent Beach. Walk out onto your patio and directly down to the courtyard area with a private back entrance for easy access to the pool area and beach access. . This unit features a King bed in the master and 2 Queen beds in the guest room. It\'s only a short walk .......read more
2 Bedroom(s)
Sleeps 6
Condo
New Listing! Sea Dream | Located in Siesta Key Village, Walk to the Beach!
Siesta Key Private vacation home
- 5.0 Star Review
Welcome to Sea Dream! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.
Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the p.......read more
Studio
Sleeps 4
Private vacation home
1 Bedroom Point of Rocks Road-next to the beach!- 3 NIGHT MINIMUM
Siesta Key Apartment
- 4.5 Star Review
Beautiful 1 bedroom unit located 1 house away from beach! Amazing Location! This beautifully decorated unit features all the conveniences of home with a fully equipped kitchen and linens provided. Enjoy the tropical pool or walk just a short distance to the beach. Point of Rocks is a small, quiet, residential neighborhood on Siesta Key, a few block.......read more
Studio
Sleeps 4
Apartment
Relaxing Siesta Key Condo
Siesta Key Condo
- 4.8 Star Review
Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or evening cocktail on the balcony with views of the beautiful inter-coastal waterway from your vacation home. Deeded beach access to Siesta Key’s famous Crescent Beach quartz sand beach is just a short stroll across the street; alo.......read more
2 Bedroom(s)
Sleeps 4
Condo
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 t.......read more
3 Bedroom(s)
Sleeps 8
Condo
Buttonwood 950 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Siesta Key Condo
Full Remodel JUST COMPLETED- Dec. 2016!!! VERY SPACIOUS 5th Floor 3BR/2BA corner unit overlooking the tranquil waters of the intracoastal waterway. The glass enclosed lanai stretches from the living room to the master bedroom. Living room is adorned in Florida decor and has TV, DVD. Master bedroom has King size bed & TV. Master bath has large walk .......read more
3 Bedroom(s)
Sleeps 6
Condo
Private Home w/Private Pool-10 min walk to Siesta Key Beach
Siesta Key Private vacation home
- 4.9 Star Review
Come enjoy this private house with your own secluded heated swimming pool, in beautiful Siesta Key. Rent for a stay of 28 days or more and our daily rate drops as it automatically includes a 15% discount.
Enjoy this private house with your own secluded heated swimming pool, in beautiful Siesta Key. Oversized private lot.
** Newly renov.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Walk to Siesta Key Beach, Pool/Spa/Tiki Bar, WiFi, Close to Village Shops, Laundry
Siesta Key Private vacation home
- 4.5 Star Review
If you are looking for a private home on Siesta Key that\'s only 460 feet from the Siesta Key Beach Access; then this is your vacation home to come to! It rests on a quiet street in a beautiful upscale neighborhood on Siesta Key just steps from playing in the sand with your kids, or reading a great novel under an umbrella with a glass of white wi.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Coral Breeze | Siesta Home, Heated Pool & Spa, Minutes to Village and Beach!
Siesta Key Private vacation home
- 5.0 Star Review
Introducing Coral Breeze, where your vacation is a breeze! This beautiful 3-bedroom / 2.5 bathroom includes a fully equipped kitchen, private heated pool and spa, spacious outdoor patio, and gas grill. Located less than 1.5 miles from Siesta Key Public Beach Access #2, you\'re able to enjoy the best of both worlds by relaxing poolside or soaking u.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Location. Four bedroom cottage, one block from beach and Siesta Village
Siesta Key Private vacation home
- 5.0 Star Review
Location. Location. Location. Our charming 4 bedroom 3 bath Florida beach cottage, which is over 1800 feet and sleeps 8 with 2 full kitchens and a fully covered porch and large patio in the back unit. Cottage is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United S.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Top in Siesta Village at Best Beaches, Food & Entertainment! Casa Van Lopik.
Siesta Key Private vacation home
- 4.9 Star Review
A Gertrude Rentals property. In the Siesta Village just a short walk to Siesta’s best beaches and sure to provide a combination of fun and rejuvenation you won\'t find in other getaways! Casa Van Lopik is 100% private with two large 3BR units capable of accommodating up to 20, and a lush tropical indoor/outdoor patio lounging and dining area. It.......read more
6 Bedroom(s)
Sleeps 22
Private vacation home
Slice of Beach Paradise | Private Wraparound Balcony with Amazing Gulf Views
Siesta Key Private vacation home
- 4.0 Star Review
Beach Road Condo Unit 2
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'
Perched by the shoreline, this 3BR/2BA townhome is a slice of beach paradise. With the Gulf just a 2-minute walk away, enjoy the stretches of sugar-white sand and turquoise .......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Siesta Key Condo
Siesta Key Condo
- 5.0 Star Review
Spacious condo, nicely furnished and private ground floor unit. 1 br, 1 ba in tropical setting, fishing pier and private beach access with great sunsets, pool, clubhouse facing the Gulf, walking distance to village, shops, restaurants and Siesta Key public beach. .......read more
Studio
Sleeps 4
Condo
Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach
Siesta Key Condo
- 5.0 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 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 degrees of a swe.......read more
Studio
Sleeps 4
Condo
- 106- Across from Siesta Key Beach with Fantastic Renovated Kitchen for large families!
Siesta Key Apartment
- 5.0 Star Review
Your ultimate vacation getaway, this two-bedroom condominium enviably situated across from Beach Access 11 at the world-renowned white sands of Siesta Beach. Located on the main level, the open floor plan boasts views of the Gulf, white sands, and magnificent sunsets. The fully equipped kitchen features granite counter tops and a large breakfast ba.......read more
2 Bedroom(s)
Sleeps 6
Apartment
Chinaberry 913 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Siesta Key Condo
- 5.0 Star Review
Brand New to Rental Program! Recently refurnished and re-decorated! Ground-level, bay front, 2BR/2BA that sleeps 6. Full Water & Bay Views! King Bed in Master, 2 Doubles in the Guest Bedroom. Large walk in Shower in Master Bath with dual-sink counter top. Walk-in shower in Guest Bathroom in the hallway. Glass and Screened Lanai perfect for relaxin.......read more
2 Bedroom(s)
Sleeps 6
Condo
2,700 sq. ft. home with private pool 200 steps to Crescent Beach - dog welcome
Siesta Key Private vacation home
Seashell Sanctuary
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'
Happiness is a private pool just 200 steps from the white powdery sands of one of the best beaches in the U.S., Crescent Beach! This single-story slice of paradise is a 2,700 squ.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Gulf and Bay Club 204C, Beach Front, Spa, 3 Pools, Sleeps 6, 2 Bedroom, Gym
Siesta Key Condo
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf and Bay Club 204C, you\'ll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. And the use of resort amenities is included! Twenty-eight-day minimum stay required.
Gulf and Bay Club 204C is available for stays .......read more
2 Bedroom(s)
Sleeps 6
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
Great Island Location - Walk to Beach, Shopping & Dining. Vista Hermosa 312A
Siesta Key Condo
- 4.4 Star Review
Great Island Location - Walk to Beach, Shopping & Dining. Vista Hermosa 312A
Beautifully remodeled condo just completed in Dec. 2020. All new kitchen including counters, fixtures & appliances. New bathrooms with updated fixtures. New dining set, living room & bedroom furniture. New lanai furniture. New flooring throughout & freshly painted. .......read more
2 Bedroom(s)
Sleeps 6
Condo
Long Term Discounts! Siesta Key Palm Island Canal-Front House Walk to Beach
Siesta Key Private vacation home
- 4.9 Star Review
Large home with 3 bedrooms and 3 bathrooms. Looks and feels like a Mexican Hacienda. Low ceilings (approx 7 foot) in the living room and bedrooms. Three sliding glass doors open up to a screened in heated pool. Walk down the paver path to a dock on the canal. At night, lights under the water allow you to see the fish swimming in the canal. Le.......read more
3 Bedroom(s)
Private vacation home
Upgraded Modern Condo on Beautiful Siesta Key!
Siesta Key Condo
This unit (405) is located on the East corridor on the fourth floor, it faces east/south with plenty of sunlight throughout the year.
There are two bedrooms in this unit, each located on the opposite sides of the living/dining room. Each bedroom has its own updated full bathrooms, king sized beds, and flat-screen TVs. Both bedrooms have views of.......read more
2 Bedroom(s)
Sleeps 4
Condo
Our House at the Beach C-120 Corner Unit!
Siesta Key Condo
- 4.6 Star Review
This Lake House offer a generous bi-level layout that includes separate dining and living room spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full size appliances including a dishwasher, microwave and full-size washer and dryer for your convenience. Off the large living room there is a balcony overlooking.......read more
2 Bedroom(s)
Sleeps 6
Condo
CA705S - COZY, COMFORTABLE CONDO on the #1 beach in the USA>
Siesta Key Condo
- 4.2 Star Review
Bright and cheery, freshly painted, new linens and some new furniture! Brand new Murphy Bed!
Living room has two loveseats and a flat screen TV.
Bedroom has a king bed, large chair and light for reading. Flat screen TV
Lanai has a gulf view of world famous Crescent Beach. Put your toes in its unique 99% quartz sand that has.......read more
Studio
Sleeps 4
Condo
Find Affordable Siesta Key Beach Hotels & Vacation Rentals
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Vacation Rentals Nearby Tampa Bay Destinations
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Rentals in Siesta Key, FL
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