Vacation Rentals in Siesta Key Sarasota.

Siesta Key Condo 4.9

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Private vacation home 5.0

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)
6 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 5.0

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)
2 Bath(s) Sleeps 4

Vacation Home

Siesta Key Condo 5.0

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 4.8

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)
2 Bath(s) Sleeps 4

Vacation Home

Siesta Key Apartment 4.9

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)
2 Bath(s) Sleeps 5

Vacation Home

Siesta Key Condo 4.9

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)
2 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 3.9

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 4.5

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.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

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)
2 Bath(s) Sleeps 5

Vacation Home

Siesta Key Apartment 5.0

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)
3 Bath(s) Sleeps 9

Vacation Home

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)
3 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 4.3

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Apartment 5.0

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)
3 Bath(s) Sleeps 9

Vacation Home

Siesta Key Private vacation home 4.9

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)
2 Bath(s) Sleeps 6

Vacation Home

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 pl.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 5.0

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 q.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 3.7

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)
2 Bath(s) Sleeps 5

Vacation Home

Siesta Key Condo 5.0

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)
2 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 4.8

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)
2 Bath(s) Sleeps 5

Vacation Home

Siesta Key Condo 4.0

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)
2 Bath(s) Sleeps 4

Vacation Home

Siesta Key Private vacation home 4.8

**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)
3 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

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

Studio
1 Bath(s) Sleeps 2

Vacation Home

Siesta Key Condo 4.9

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

1 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Siesta Key Cottage 4.8

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)
2 Bath(s) Sleeps 4

Vacation Home

Siesta Key Private vacation home 5.0

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)
2 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 4.8

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 4.8

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)
2 Bath(s) Sleeps 6

Vacation Home

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Private vacation home 2.5

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)
3 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 4.6

MIDNIGHT COVE GULF SIDE, GULF VIEW!!! LOCATED DIRECTLY ON SIESTA KEY BEACH, VOTED THE NUMBER ONE BEACH IN AMERICA! Located just steps from the legendary white powder sands of Siesta Key Beach. This is the perfect location and condominium for a perfect vacation! Nicely updated throughout, this delightful unit offers all the comforts of home and a .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Apartment

Dates Available November 10th - 30th or December 6th - 30th or Jan 5th - 30th - 2022. A brand new remodeled condo at Harbor Towers Yacht and Racquet Club! Don't miss out on the beautiful Florida sunrise right from the comfort of your vacation home. Water views from the living room and both bedrooms! Enjoy the view of the water, or the boats going b.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Siesta Key Private vacation home 3.0

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)
3 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

Fabulous totally remodeled 3 bedroom 2 full bath full gulf view unit! The unit is on the 4th floor in a 7 story building. Approximately 1600 Sq. ft. of living space. Master bedroom features King "Sleep Number" bed, large walk-in closet, with view of beach and glass sliders out to the screened lanai. Master bath has dual sinks and large, gorgeous st.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo

Enjoy your stay on Siesta Key Beach!

Whispering Sands condo is located right on Siesta Key Beach and just a block from the Siesta Key Village, where you can enjoy countless restaurants, cafes, bars and boutiques.

Kitchen, Living Room and Master Bedroom all have beautiful views of the Gulf of Mexico. Master bedroom has a queen size b.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Siesta Key Private vacation home

DIRECTLY ON #1 BEACH, SIESTA BEACH
Experience the breathtaking views of this beachfront home! Located directly on Sunset Beach on Siesta Key, this 4-bedroom 4-bathroom home is a must. Inside, this home is beautifully decorated and can comfortably sleep up to 12 guests. This home comes equipped with a full kitchen, a dining area, and a spacious l.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 12

Vacation Home

Siesta Key Condo 3.0

Take a look at this beautiful newly remodeled and redecorated unit! Ground floor 2/2 1400+ sq. ft. with slider glass enclosed lanai for a little more privacy. Open the sliders and still get the screened lanai effect and experience the cool tropical breeze from the Gulf of Mexico. Kitchen and baths have granite counter tops and all flooring is cove.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo

Beautifully and recently updated 3BR/2BA private, end/corner unit with ceramic tile floors in all living areas. Completely renovated bathrooms, tile showers with rain shower heads in both bathrooms, newly tiled and painted master bedroom and second bedroom. All new fans with lights in condo. New glass lanai doors and all new windows. Spacious with .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

Fabulously decorated 3/2 corner unit on the seventh floor. Wood flooring and ceramic tile throughout. The updated kitchen and baths adorn granite counter tops. Decorated with soft leather sofa and chairs, the living room comes with TV/VCR/DVD. Step out onto the screened lanai and feel the subtle tropical breeze. Experience the view of Crescent Beac.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

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)
2 Bath(s) Sleeps 6

Vacation Home

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 4.0

Brand New to the Rental Program! Absolutely GORGEOUS 2 bedroom 2 full bath unit on the 2nd floor in the main tower on the Gulf Side. Overlooking the beautiful tropical grounds, pool and the famous, white sugary sands of Crescent Beach! Tastefully decorated in a very light and bright, modern beach-theme, leather furniture in the living room, very up.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 4.9

1 bedroom 1 bathroom condo with access to private beach
Ground floor villa (750 sq ft) with patio (non-smoking)
Newly renovated kitchen and living room with big screen TV
King bed in bedroom with another big TV
Two recliners and fold-out sleeper sofa that fits two more guests
Internet access, refrigerator, ice maker, microwave, dishw.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Siesta Key Private vacation home 4.8

Location, Location, Location. Comfortable recently refreshed with new interior paint, baseboards, ceiling fans, lighting, and the carpet in the bedrooms has been replaced with Pergo flooring. This 3BR, ground level house, is just steps to Siesta Key Beach, #1 Beach in the USA, 2011 & 2014 located on the "Heart" of Siesta Key's Grand Canal." Roma.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 4.7

AMAZING views from this 5th floor 2BR/2BA condo overlooking the Beach and the Gulf! Brand New to our Rental Program! Spacious living, dining, lanai and kitchen, all with views of the water! King bed in master bedroom, full view of the water, with glass sliders out to the lanai. Very spacious master bath with large soaking tub (no shower.) Two twin .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

**** 7 Night Minimum from Saturday to Saturday ONLY!**** Spacious 1600+ sq. ft. 3/2 ground floor unit. Step out lanai and back door to pool and beach! New flat screen tv's in living room and all bedrooms, king bed in master bedroom. Step-in shower/roman tub in master bath. Guest bedroom has queen bed and guest bath has a tub/shower combination. 3rd.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo 5.0

PEPPERTREE BAY CONDO - ON THE GULF BEACH ON SIESTA KEY - This is a fully furnished 2 Bedroom, 2 Bath, condo. It was fully renovated in 2017. There is an elevator. All new stainless appliances, furniture, granite counter-tops, tiled floors, raised ceilings, and we've incorporated the lanai into the main living area (with AC) for more living space .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home