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Vacation Rentals in Siesta Key Sarasota.

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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Siesta Key, Florida.

Parrot Beach Cottages Suite #4 - Siesta Key Studio

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach!

Parrot Beach Cottages Suite #4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Parrot Beach Cottages on Siesta Key is mere steps - approximately 150 feet - from the beach and the emerald water, situated just behind the waterfront properties and within walking distance of Siesta Key Village. Occupying roughly 275-300 square feet, Suite #4 is small but fully .......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Studio Rentals

Vacation Home

Siesta Key Escape - Siesta Key Condo

Siesta Key Escape- Bay Oaks on Intercostal

Start your vacation at our cozy 2 bedroom, 1 bathroom fully furnished beach condo. Centrally located on the island, just off the mainland of Sarasota, this tranquil resort sits waterfront on the bay, just a short walk to the famous white powder sands of Siesta Key beaches. Rich with amenities: fishing pier, heated pool, waterfront grilling & picnic area, tennis & pickleball court, a bus stop for the free island shuttle, clubhouse with kitchen,.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

BLUE LAGOON - Bring Your Pets! - Siesta Key House

Tropical Bungalow 5 min walk Beach-15 min Village, Monthly Rental, Pet Friendly

SHORT WALK TO FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. The Blue Lagoon is the perfect tropical getaway right in the heart of Siesta Key in the quiet and welcoming Palm Island neighborhood - just steps away from the award-winning white sand beach or an equally short stroll to Siesta Key Village; which has amazing shops and plentiful restaurants. The Blue Lagoon is in such a fantastic location, so close to everything Siesta Key ha.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Vacation Rentals - Siesta Key Condo

Gulf View Condo, Water access

Completely updated 1 bedroom (with upstairs loft with 2 trundle beds sleepin 4 total-loft is completely open) 1 bathroom. The downstairs has a queen bed in the master bedroom with its own TV, dresser, closet and sitting area. The bathroom, living room, kitchen and dining (that can sit up to 6) are all down stairs. There is a view of the gulf from every room in the house. Upstairs, you will find two separate trundle beds, each accommodating two gu.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 8 Condo Rentals

Vacation Home

B04 - Siesta Key Villa

Casa Blanca B04 Villa

2 Bedroom/ 1 & 1/2 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach. This newly furnished and decorated 2 bedroom villa with a brand new king mattress, and sleeper sofa, accommodates up to 6 guests. The master bedroom offers a king bed, private bath and cable TV. The guest bedroom offers 2 twin beds and cable. Villa B4 offers HD TV, DVD, movie choices, surround sound, and wireless internet services. F.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Villa Rentals

Vacation Home

B17 - Siesta Key Villa

Casa Blanca B17 Villa

2 Bedroom/ 2 Bath Large Private Villa, Private Wireless, DVR & Free HBO, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach. Unit B17 is under new ownership and has been freshly painted with new tile throughout as of January 2016. It features a brand new queen sofa sleeper as well as high-speed private premium Wi-Fi. This unit is only steps to the beach and would be the perfect place to enjoy your next family vacation or cou.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Villa Rentals

Vacation Home

Our House@theBeach unit 109 - Siesta Key Condo

Walk to beautiful Siesta Beach

Lovely townhome with all the amenities of home. Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony a.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

D08 - Siesta Key Villa

Casa Blanca D08 Villa

1 Bedroom/ 1 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach. Welcome to your home away from home! Casa Blanca unit D08 was entirely renovated at the end of 2015. Everything inside is brand new and beautifully updated. Features include a king size bed, walk-in shower, new furniture, new appliances, and brand new tile throughout. Casa Blanca is within walking distance of Crescent Beach Village restaura.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Villa Rentals

Vacation Home

Vacation Rentals - Siesta Key Condo

Two bedrooms, two baths, 35 ft. enclosed lanai, new appliances and newly renovated d

Whispering sands is a fifty five and over well manicured community that is located in the gut of of Siesta Key. It is a hop skip and a jump to the beach and on the other side you can simply walk out the gate and you will be immediately consumed by a jovial crowd as they are mesmerized by the tropical aura this town generates. The sunsets are simply divine and it is a local ritual to witness the sunsets every night because of its dynamics that .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Jamaica Royale Siesta Key - Siesta Key Condo

Beachfront Condo! Shown on HGTV! Renovated in 2020. Sleeps 4

-Be one of the lucky few to call this your home for the week! This unit was shown on HGTV in April of 2019. We have included some still shots from the episode to display the unit as shown from the episode. -1st floor unit* 1 story building, no neighbors above or below for you to worry about being noisy 🙂 1 King bed and 1 Pullout sofa. Both are brand new beds (2018). -728 Sq feet, renovated in 2020 -Unit is professionally cleaned after every gue.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Fern Haven - Siesta Key Studio

Fern Haven Studio Cottage - walk to Siesta Beach and Village Pets Welcome!

SHORT WALK TO FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. Fern Haven is a Key West style studio efficiency. It is comfy, cozy, bright and airy with French doors onto a deck overlooking gardens and brick patio and walkway to a shared hot tub. It has a large mirrored doored closet and under bed drawers for ample storage. It is situated in a quiet neighborhood with only a short walk to the famous Siesta Key beach and village. Across t.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Studio Rentals

Vacation Home

A Slice of paradise... - Siesta Key Townhome

Elegant - Spacious - Private Townhome - steps aways from Siesta Key Beach

Need a “flexcation" near the Florida beach? If you can work from anywhere - why not work from sunny Florida and get some Vitamin D? This raised first floor townhouse style condominium has a 6ft deep balcony with WIFI reaches out to the balcony so you can stay connected while you enjoy the warm Florida weather. There is also WIFI available at the condominium complex's community pool. Stay a minimum of 28 days and get a discount! ELEGANT & SPA.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

Vacation Rentals - Siesta Key House

Beautiful Siesta Key 2 Bedroom Condo!

Well appointed 2 bedroom, 2 bath condo at the corner of Midnight Pass and Stickney Point Roads. Private access to the beach just steps away. Master bedroom features two Queen beds and adjoining bathroom with walk-in closet. Second bedroom has two twin beds, two spacious closets and shared bath. The kitchen is fully stocked with everything you need to stay in! There are three balconies, one off the main family room, one off the second bedroom a.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

609 CS Tower 2BR 2BA Sleeps 6 - Siesta Key Apartment

Crystal Sands Tower Unit 609 - Beachfront

Crystal Sands #609 has been totally renovated and tastefully decorated with a king in the master and two queen size beds in the Guest bedroom. The view from this sixth floor unit is perfect; not too low and not too high. Beautiful Gulf of Mexico views with sunsets year round from the screened lanai that is accessible from the living room and both bedrooms. Our Accommodations are just 2 miles from the popular Siesta Key Village with shops, resta.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Apartment Rentals

Vacation Home

REZRentals -Crescent Arms 703N - Siesta Key Condo

REZRentals - Crescent Arms #703N - 2 Bedroom / 2 Bathroom Gulfview

Property Details Crescent Arms #703N has been updated with a newer kitchen, new furnishings, (3) new LED TVs, new king bed and (2) new queen beds.  The lanai has a direct view of our world famous Crescent Beach with our own private beach.  Quick ride down the elevator, (50) steps to the beach. •   3D Virtual Tour:          https://my.matterport.com/show/?m=jzysYrBTxDY •   Minimum Rental Age:  (30) years old •   Rooms:    .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

REZRentals - Sea Shell 105 - Siesta Key Condo

REZRentals - Sea Shell 105 - Renovated - 2 Bed / 2 Bath - Open Lanai

Sea Shell #105 was completely renovated Summer 2015, everything is still like new. Conveniently located to the south end of Siesta Key within easy walking distance to restaurants, shopping and entertainment. -------------------------------------------------- Property Details -------------------------------------------------- Sea Shell #105 is approximately (120) steps from front door to our #1 Beach. --------------------------------------------.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Vacation Rentals - Siesta Key Condo

Lovely Condo with Sunset Views and All the Amenities

You are going to love this vacation! Spacious fully equipped 5th floor condo across the street from the Gulf of Mexico at Bay Oaks. Public beach access less than a mile away. Free trolley with stop in front of complex. Fish from a private dock or sun on one of the world's cleanest and coolest white sand beaches. Amenities include but not limited to a cool refreshing heated pool, club house with pool table, HD cable TV, high speed internet, and s.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Vacation Rentals - Siesta Key Condo

Anchorage 909 in Siesta Key

*EARLY WINTER SPECIAL* 20 % OFF A STAY OF 7 NIGHTS OR MORE NOV. 27th THRU DEC.17th, 2021 We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

C06 - Siesta Key Villa

Casa Blanca C06 Villa

2 Bedroom/ 2 Bath Large Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach. This lovely unit has just been remodeled and is awaiting your arrival. There is free high speed internet and long distance telephone in the U.S. and Canada, heated pool and screened lanai. This unit can occupy up to 6 persons. Villa C6 features new living room furniture, a 50" Plasma HDTV with DVD/VCR and a CD player in the open living.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Villa Rentals

Vacation Home

Bay Oaks Condominium - Siesta Key Condo

Beautiful one bedroom condo on Siesta Key. minutes from Siesta key Beach!

Beautiful 4'th floor condo with elevator access. screened in lanai, all the essentials, and beach chairs, umbrellas, cooler with wheels and big beach bag and towels. a one mile drive to Siesta key beach and a 10 minute walk to Crescent beach. tennis court, fishing dock and BBQ area with picnic tables on the intercoastal waterway. Heated swimming pool, coin op laundry, and club house with pool table, lounge area and tourist info brochures........read more

1 Bedroom(s)
1 Bath(s) - Sleeps 3 Condo Rentals

Vacation Home

Vacation Rentals - Siesta Key Condo

Entire Condo Beach Getaway

Updated 2 bedroom 2 bath lagoon view unit, steps to public beach. Enjoy coffee overlooking the lagoon and watching dolphins and manatees swim by. Beautiful pool deck with updated party room. Grill and entertain using one of four Weber grills for building use. Workout in the updated gym and excessive room or tennis courts. Sit by the lagoon under the beautiful pergola. Have dinner alongside the logoon in the sitting area. Parking included........read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Vacation Rentals - Siesta Key Condo

UNIT 2 at SIESTA KEY Beach Villa

Wonderful modernized and well maintained condo (1 of 2) in a Key West Style house. The unit has been completely refurbished. Flat screens and free internet are complimentary available .Large heated community pool and gated beach access are just a few meters away (3 min walk, about 250 yds)........read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Vacation Home

D12 - Siesta Key Villa

Casa Blanca D12 Villa

2 Bedroom/ 2 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach. This unit features a King bed in the master with a brand new bathroom, the guest bedroom offers a queen bed where there is a washer and Dryer in the unit for your convenience. The Second bathroom was added in late 2013. There is a new kitchen that will delight the chef in each of you. The living room offers a sleep sofa for additional guest.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Villa Rentals

Vacation Home

Vacation Rentals - Siesta Key House

4 Bdr Beach House

Perfect for 2 Families!! Just minutes from the beach, marina, and village center, your tropical paradise awaits you at this bright, spacious 3 bedroom, 2 bathroom vacation rental house. This well-appointed property boasts a private screened-in pool with jacuzzi tub. There’s even a putting green on site for you golf fanatics to polish your skills. Families can decide between enjoying the private pool, nearby beach with private access, charter bo.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 14 House Rentals

Vacation Home


Siesta Key Beach, Florida.

Consistently ranked in the top spot as the most beautiful beach in the United States, Siesta Key is the ultimate beach escape. An eight-mile barrier island with stunning natural beauty, this award-winning beach is known for its pristine sugary white sand that is often described as the finest in the world. Siesta Beach, Turtle Beach and Crescent Beach are the most popular along the barrier island, offering tranquil waters that provide a safe spot for swimming and snorkeling.

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