Vacation Rentals in Siesta Key Sarasota.

Siesta Key Cottage 3.0

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.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

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 4.8

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)
2 Bath(s) Sleeps 6

Vacation Home

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 t.......read more

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

Vacation Home

Siesta Key Condo 5.0

No better deal around! Top of the line on Siesta Key! It really doesn\'t get any better than this. This 2 bedroom / 3 bathroom unit has all the top of the line finishes that you would expect, such as Wolf gas stove, Sub Zero refrigerator, flat screen TVs in all rooms, high-speed internet, and more! This over the top unit will amaze you at every tur.......read more

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

Vacation Home

Siesta Key Condo 5.0

Location, Location, Location! We are located directly on the Gulf of Mexico on the best part of Crescent Beach. #1 in the world by National Geographic Magazine. #2 in America\'s Best Beaches-2012\' by Dr. Stephen Leatherman, AKA Dr. Beach.
Welcome to our spacious condominium, minutes from great shopping, restaurants, and more! Enjoy this beauti.......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 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 4.9

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 t.......read more

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

Vacation Home

Siesta Key Condo 4.3

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 Apartment 4.7

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 5 with a king in the master, a full and twin.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5

Vacation Home

Siesta Key Condo 4.6

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Condo

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. Th.......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 Apartment 4.5

Your ultimate vacation getaway! Bright and breezy 2 bedroom/2 bath condo across the street from Beach Access 11 at the world-renowned white sands of Siesta Beach.
Located on the main level, the open floor plan and beachy décor will fill you with good vibes. Enjoy morning coffee or pre dinner cocktails from your private outdoor patio. The maste.......read more

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

Vacation Home

Siesta Key Apartment 4.4

This studio condo is approx 420 sq feet and offers a king size bed. Play tennis or shuffleboard, then bask in the sun by the swimming pool located steps from your unit. Stroll down palm lined walkway that lead to Siesta Key\'s fine white quartz sand and enjoy one of Florida\'s spectacular sunsets. Lounge chairs are conveniently located on the beach.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

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 5.0

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.......read more

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

Vacation Home

Siesta Key Cottage 4.0

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 offers a private parking space directly outside your front door.......read more

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

Vacation Home

Siesta Key Apartment 3.7

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 c.......read more

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

Vacation Home

Siesta Key Apartment 3.9

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 c.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 7

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 Condo 5.0

Beautifully updated 2 bedroom, 2 bathroom with loft, gulf view unit. This unit is new to the Rental Program as of June of 2019. The master features a king size bed, updated bathroom with a shower and side porch with a view of the water. The guest room has a king size bed. For convenience, the washer/dryer is in the guest room closet. The guest bath.......read more

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

Vacation Home

Siesta Key Condo 4.0

If you\'re looking for a great vacation location on beautiful Siesta Key, then look no further than this 2 bedroom/2 bath unit that sleeps 6 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.......read more

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

Vacation Home

Siesta Key Private vacation home 4.6

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 c.......read more

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

Vacation Home

Siesta Key Condo 4.0

Enjoy this beautiful condominium in Midnight Cove II! Watch the boats go by from your open 3rd floor Bay front balcony! Updated unit with new kitchen, newly upgraded master bath with walk in shower, and washer and dryer. Enjoy a game of tennis at of their nicely appointed tennis courts, or a dip in the pool at their invitingly large community pool.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5

Vacation Home

Siesta Key Private vacation home 4.9

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)
3 Bath(s)

Vacation Home

Siesta Key Condo

Beautiful updated, modern 2 bedroom, 2 bathroom coastal condo overlooking the pool and Gulf of Mexico.
This unit features updates throughout:
The kitchen features unique leathered marble counter tops, stainless steel appliances and custom cabinets.
The bedrooms and bathrooms feature modern furniture and luxurious updates. The master bedro.......read more

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

Vacation Home

Siesta Key Cottage 5.0

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 parki.......read more

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

Vacation Home

Siesta Key Private vacation home 4.9

NEW OWNERS and 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 mo.......read more

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

Vacation Home

Siesta Key Condo

This 2 Bed/2 Bath boasts gorgeous bay views, high-end finishes, and a spacious layout with cathedrals ceilings. Updated kitchen with stainless steel appliances, in-unit washer/dryer, full sleeper sofa and 3 TVs.

If you are looking for a luxury getaway with an unbeatable location this unit has it all!

Exclusive amenities include:read more

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

Vacation Home

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)
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

Tropical, laidback, and filled with island flair, this two-bedroom condominium enviably situated alongside the world-renowned sands of Siesta Beach. Located on the second level, the open floor plan boasts views of the Gulf, white sands, and magnificent sunsets. Enjoy morning coffee or pre dinner cocktails from the Sunroom. The master bedroom featur.......read more

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

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 Condo 5.0

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 Cottage 4.2

Updated recently in the kitchen with a quartz counter top and all new appliances! Also, many new furniture pieces including a beautiful dinning table set (seats 8), a king "Tommy Bahama Paradise Point Plush" mattress set in the master bedroom, and a queen "Perfect Sleeper Plush" mattress set in the second bedroom. Also a queen sleeper couch was r.......read more

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

Vacation Home

Siesta Key Apartment 4.5

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

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

Vacation Home

Siesta Key Private vacation home 5.0

Updated home in quiet neighborhood just off the beaten path to the Village and Beach. Walk to all of your favorite restaurants and shops. This is a private home with lush landscaping and surrounding privacy wall. Main Floor Master Suite and guest bedroom, upper level has a second master suite with another guest bedroom. The home sits on a corne.......read more

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

Vacation Home

Siesta Key Private vacation home 4.9

How far from the Beach? 150 steps or barely a 2 minute walk and you\'re on the Beach! Short walk to Siesta Village loaded with restaurants, bars, shopping, clubs and more!
Welcome to Convenience on Siesta Key - Wonderful, Clean & Cozy 2 bedroom, 2 full bathroom, single-level Villa that comfortably sleeps 4 adults. Enjoy 1000 sf of living s.......read more

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

Vacation Home

Siesta Key Private vacation home

This is a beautiful condo across the street and through the public parking access to the beach. The unit has 2 bedrooms, 2 baths, and a trundle bed . Comfortably sleeps six. We have a one car garage and an assigned parking space. The complex has tennis courts and a pool. The prize of this unit is the balcony that overlooks a beautiful lake, from t.......read more

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

Vacation Home

Siesta Key Private vacation home 4.9

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)
2 Bath(s) Sleeps 8

Vacation Home

Siesta Key Condo 5.0

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

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

Vacation Home

Siesta Key Private vacation home 4.8

This Lovely, fully updated 3 bedroom property that holds 4 Adults and 2kids.Its also is a 3 bath canal home 1 block from Siesta Village! Tropical private pool setting just off the main living area and the grand Master Bedroom. Second Master suite with private bath including soaking tub. All bathrooms completely redone in 2015. Quiet street literall.......read more

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

Vacation Home

Siesta Key Condo 4.5

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.

King Master with views.......read more

2 Bedroom(s)
2 Bath(s)

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)

Vacation Home

Siesta Key Private vacation home 4.5

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)
2 Bath(s) Sleeps 6

Vacation Home

Siesta Key Private vacation home 4.5

How far from the Beach? 150 steps or barely a 2 minute walk and you\'re on the Beach! Short walk to Siesta Village. Welcome to Prime-Time on Siesta Key - Wonderful, Clean & Cozy 2 bedroom, 2 full bathroom, Two-Story Villa that comfortably sleeps 4 adults. Enjoy 1000 sf of living space with huge upstairs living room, comfy couches, TVs in all rooms .......read more

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

Vacation Home