Vacation Rentals in Siesta Key Sarasota.

Stunning Siesta Key-2B/2B Full Bayfront Condo

Experience spectacular intracoastal bay views in this FULL BAYFRONT condo. Relax while watching the parade of boats in the bay through the custom trifold sliding doors on the lanai or walk outside to the private patio equipped with brand new dining table and four outdoor chairs. This unit is directly on the path to the new private fishing pier. First floor means there are no steps to climb. Condo has been professionally remodeled and impeccably maintained. This unit features 2 bedrooms/2 full bathrooms with granite counter tops, custom/furnitu.......read more

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

Vacation Home

Casita Sol - Ask About $99 Down!

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer! We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened our cleaning crews by mandating the highest quality products that are EPA approved to use against COVID-19. Our cleaners also have a longer period of time to complete this thorough proc.......read more

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

Vacation Home

Sunset Royale - 204- Close to Beach and Siesta Village

Enjoy watching the beautiful sunsets every night from your own private lanai/patio in this one bedroom, one bathroom condo. Located at Siesta Beach with Siesta Key's famed "Village" a short walk away. This condo has everything you are looking for. Amenities include: beach access, BBQ, picnic tables (at the beach), Gulf view, western sunsets, family environment with golf, jet skis, parasailing, boat rental, fishing close by and much more! 1 WEEK MINIMUM RENTAL REQUIRED.......read more

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

Vacation Home

Our House at the Beach E-704 Best view of the Gulf!

Just across the street from the acclaimed #1 Beach in the US. This beautiful two bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities include a heated pool, tennis courts and a covered pavilion with grilling area........read more

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

Vacation Home

Sunsets Abound in this stunning 2 bedroom right across from Siesta Key Beach,

Location, location, location. Bright and beachy open floor plan beachfront condo right across the street from the famed white sands of Siesta Key and a mile from Siesta Key Village.From the moment you walk through the door, this elegant third floor condo has everything you need for your stay in Paradise. The views alone will leave you coming back year after year. The kitchen features white Corian countertops and is fully equipped for all your needs. The queen-sized master bedroom has a large window that provides beautiful gulf views, a private.......read more

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

Vacation Home

Tivoli by the Sea-Unit 202- Nicely updated!

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen and a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets! This unit sleeps 6 with at king in the master a queen in the guest and a queen sleep sofa. 1 week minimum rental.......read more

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

Vacation Home

LuLu Green in the heart of Siesta Key Village, 4 minute walk to beach, Pool, Washer/dryer

Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could want and need at your fingertips; I assure you that you will never want to leave LuLu's Key House! We provide everything for your stay! This second level 1bedroom, 1 bath condo with a heated communal pool has been completely renovated top to bottom,.......read more

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

Vacation Home

Aloha Kai - Unit 31- close to the beach!

Fully furnished villa offering living room, dining area, fully equipped kitchen, two bedrooms and one bathroom. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offer a private parking space directly outside your front door. The kitchen in each villa is fully equipped with appliances, pots, pans, utensils, and dishes for all your food preparation needs. Unit is equipped with washer and dryer and an outdoor shower........read more

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

Vacation Home

Aloha Kai - 2 beautful unit and close to pool!

Fully furnished villa offers living room, dining area, fully equipped kitchen, two bedrooms and 2 bathrooms. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parking space directly outside your front door. The kitchen in each villa is fully equipped with appliances, pots, pans, utensils, and dishes for all your food preparation needs........read more

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

Vacation Home

Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront condos are walking distance to South Village. Crescent Arms has one-story villas as well as two seven-story towers that are directly on the beach. Our vacation condos are located in the South Tower of the Crescent Arms Condo complex. Crescent Arm.......read more

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

Vacation Home

Island House Beach Resort V37

Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 1000 sq. ft. and is 2 bedrooms, 2 baths. The villa has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, screened lanai, covered parking, 3 tvs, dvd, free wi-fi in unit! It is only steps to the beautiful azure and turqouise waters of the Gulf of Mexico. The beautifully maintained complex has 2 beach cabanas, beach chairs, large heated swimming pool, game room, sh.......read more

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

Vacation Home

Siesta Dunes 5-303, Come enjoy our little piece of Paradise!

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 a short walk from the lovely beach. Let’s face reality. If you’re coming to Siesta Key, you want to be on the beach. You'll appreciate the privacy and value when you skip the crowded hotels, a.......read more

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

Vacation Home

Private Beach, Full Gulf Views, Wifi/Cable, Heated Swimming Pool Overlooking Ocean, Walk to Village

Experience the most amazing #1 rated Siesta Key beach views on the Gulf of Mexico from the 15th floor of the Terrace Building in Siesta Key Village! Hands down, best location with the best views! This home away from home 2 bedroom 2 bath condo with almost 1,187 sq. ft. being almost 1/4 of the entire 15th floor is located right on Siesta Key Beach and in Siesta Key Village with gulf views, bay views, city light views, Big Pass Lido Key Beach views. Gorgeous heated swimming pool overlooking the ocean, game & gym room, community room, assigned .......read more

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

Vacation Home

Island House Beach Resort V27

Island House Beach Resort, Siesta Key Florida- Crescent Beach - This large 2 bedrooms, 2 bath villa is non-carpeted and approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, covered parking, central ac/heat, free wi-fi in unit! The unit has a king size bed, 2 twins, sleeper sofa. The unit is just steps to the crystal blue waters of the Gulf of Mexico. This beautifully maintained complex has 2 beach cabanas, beach chairs, large heated swimming pool, game room and a scenic beachfront.......read more

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

Vacation Home

Tivoli by the Sea-Unit 503 - Beautiful view

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets! This unit sleeps 4 with a king in the master, and two twin size beds in the guest bedroom. 1 week minimum rental........read more

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

Vacation Home

Our House at the Beach W-301 Stunning panoramic beach views

Looking for an amazing location with access to the most beautiful beach? Look no further! This 2-bedroom, 2 bath condo (sleeps 6) on Siesta Key sits right across from the Siesta Key Beach, voted #1 Beach in USA. This large condo is light and bright with two large wrap around balconies, 50' of floor to ceiling windows, and has a great view the ocean. It's stylish and recently renovated with everything you need for a restful and memorable vacation. The condo is in the “Our House at the Beach” condominium complex, directly across from the mai.......read more

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

Vacation Home

Contemporary Garden View, Ground Floor Unit, Short Walk to Pool/Beach

Ground floor unit, garden view 2 Bedroom, 2 Bathroom Unit. Updates through out which include new tile flooring as well as bathrooms and a new kitchen with stainless steel appliances. Contemporary tiles and finishes give the unit a bright and clean feeling. Enjoy sitting in the back patio overlooking the garden which is accessible through the master bedroom or lanai. This very quiet and peaceful location is only a short walk from the beach, pool and grill area. Amenities Include: Garden View King bed in the master bedroom Large shower in mast.......read more

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

Vacation Home

Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Beach w/Private Yard

Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute typical afternoon showers which freshen the air and quickly lead back to a wonderfully sunny summer day here at the beach. The yard is green and canopied, the street is quiet and sleepy and the beautiful cottage is nestled in between the trees. A pe.......read more

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

Vacation Home

Walk to Beach, Heated Pool, Tennis, Fishing Pier, Distant Gulf View from Master, Elevator Bldg. WiFi

Come vacation in this beautiful two bedroom, two bath condo with lots of amenities at your fingertips in a relaxing atmosphere. Bay Oaks condominium complex on Siesta Key, Fl is set among tropical foliage and beautiful walkways throughout. Enjoy a stroll along the coconut palm trees and tall shade oaks that line the brick pathways throughout Bay Oaks. You will have access to the complexes private fishing pier, the tennis courts, pool table in the clubhouse, BBQ area, sauna, a heated swimming pool, plus it is a short distance from world renown.......read more

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

Vacation Home

Island House Beach Resort 9S

Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft., non-carpeted and has a large living area, dining area, fully equipped kitchen, all appliances, lanai. It has a king, 2 twins, Central heat/ac. Free Wi-Fi in unit. This beautifully maintained complex is located on the widest part of one of the best beaches in southwest florida. The condo offers a view of palm trees, white sand, and the azure and turquoise waters of the Gulf of Mexico. The complex has 2 beach cabanas, be.......read more

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

Vacation Home

Chinaberry 423 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

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 updated kitchen with an open floor plan. The colors of the unit are off white and pale blue. Beautiful plank tile throughout the unit. Very cozy lanai with lounger seating and a bar top counter for morn.......read more

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

Vacation Home

Siesta Beach House #106 Beautiful Updated Unit

Modern decor, new bedding this is a great 1 bedroom unit at the Siesta Beach House. This unit sleeps 4 and is equipped with a King bed and a sofa bed. If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico BOOKING REQUIR.......read more

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

Vacation Home

Steps from World-Famous SiestaBeach*Spacious 2/2 Condo w/garage*tranquil setting

Incredible, beautiful SIESTA BEACH *2020 Tripadvisor ranks Siesta Beach #1 top beach in the US and #11 in the WORLD (based on travelers reviews & ratings) "pristine beach that never seems to end. A place in the sun that warrants returning again and again." *2018 named #2 beach of "the 50 most Beautiful Beaches of the World" *2017, 2011 named America's Best Beach - based on 50 criteria evaluated by "Dr. Beach" Stephen Leatherman *2017, 2015 named #1Beach in the US and #5 in the World .......read more

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

Vacation Home

Tivoli by the Sea-Unit 606 - Tivoli by the Sea-Unit 606 - Amazing full Gulf view!

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen and a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!! This unit sleeps 4 with a king bed in the master, and a king bed in the guest bedroom. 1 week minimum rental........read more

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

Vacation Home

Our House at the Beach C-217 A MUST SEE!!!!!!

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 and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Lake House offers central A/C, a.......read more

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

Vacation Home

Anchorage Resort 4th floor condo in Siesta Key with private beach access, pool, boat dock!

Palm tree lined views and gorgeous sunsets are all what this vacation home is about! Located just minutes from the beaches of Siesta Key, this home will be your new vacation destination. With 2 bedrooms and 2 bathrooms, you and your guests will be coming back time and time again. When you open the front door to this home, you soon realize this is not like most vacation homes. Your eyes are drawn to the patio which boasts floor to ceiling sliding glass doors. Palm trees sway in the ocean breeze as you sit outside. The sliding doors turn the liv.......read more

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

Vacation Home

Aloha Kai - Unit 14A-close to beach and pool!

Nicely renovated and Fully furnished villas offer living room, dining area, fully equipped kitchens, 1 bedroom/ 1 bathroom. Screened porch. Short walk to the beach or pool. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parking space directly outside your front door. The kitchen in each villa is fully equipped with appliances, pots, pans, utensils, and dishes for all your food preparation needs........read more

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

Vacation Home

Fantastic 2 bedroom / 2 bath Direct Gulf Front Condo!- 2 wk minimum

This fantastic 2 bedroom / 2 bath Direct Gulf Front condo is the perfect place for your Siesta Key vacation. This condo is equipped with a King bed in the master, a Double and 1 twin in the guest bedroom and a Twin sofa bed in the living room. Grab the Siesta Key Trolley, and take in the views of our beautiful Island which is brand new this year- and no cost to you- free for everyone!! 1 MONTH MINIMUM JAN-APRIL, 2 WEEK MINIMUM MAY-DECEMBER. (SATURDAY TO SATURDAY BOOKINGS ONLY JAN- JULY) Tenant agrees to rent the unit as specified in the TSA re.......read more

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

Vacation Home

6536 South Village Pool Home

Fantastic 3 bedroom, 2 bath pool home on a Natural Lagoon located in the South Crescent Shopping area! Enjoy lounging in the small, heated pool, or sitting on the dock by the lagoon. Just a short walk to many fantastic restaurants and great Beach shopping for everyone! Enjoy having The Crescent Grocery at the end of your street and our world renowned Siesta Key Beach just a short walk away. This beautiful home is pet friendly- so leave no loved ones behind! BOOKING REQUIREMENTS: 1 WEEK MINIMUM RENTAL REQUIRED AND SATURDAY TO SATURDAY ONL.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Apartment Rentals

Vacation Home

Our House at the Beach C-102- Near Beach and Pool!

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 and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Each Lake House offers central A.......read more

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

Vacation Home

Our House at the Beach C-122 Updated First Floor

Lake house offers 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 grounds. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Lake House offers central A/C,.......read more

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

Vacation Home

NEW LISTING! Updated 2 Bedroom, 2 Bath Gulf View with 2 Lanais!

Siesta Dunes 2-300: END UNIT with 2 LANAIS!!!!! Our third-floor condo will allow for you to take in an aerial view of the Gulf of Mexico, which is noted for Siesta Key’s spectacular sunsets! In addition to the front screened in lanai that offers incredible views of the pool, beach deck, beach, and gulf, a bonus awaits you with a second side lanai. It’s worthy of noting that our condo is the only 2-bedroom condo out of all of Siesta Dunes that has a side lanai, which provides a full view of the Gulf of Mexico!! This extra living space/side l.......read more

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

Vacation Home

Harbor Towers Bay View, pools, tennis, gated, high speed WiFi, Parking

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 the beach! Fabulous powdery white sands of Siesta Key Beach are just a short bike ride or Trolley ride away. A heated pool and a smaller wading pool for children are waiting for you. Considered one of Siesta Key's nicest pools, they are kept at a comfortable 85 degrees all year round. You can fish right off of the docks, have a picnic overl.......read more

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

Vacation Home