Siesta Key Vacation Rentals & Homes by Owner

Siesta Key Cottage 3.0 Star Review

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

Siesta Key
1 Bedroom(s) - 1 Bath(s)
Cottage Rental Sleeps 2

Siesta Key Private vacation home 5.0 Star Review

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

Siesta Key
4 Bedroom(s) - 6 Bath(s)
Private vacation home Rental Sleeps 8

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

Siesta Key Condo 4.9 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

Siesta Key Condo 5.0 Star Review

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

Siesta Key
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 6

Siesta Key Condo 5.0 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Siesta Key Apartment 4.9 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Apartment Rental Sleeps 5

Siesta Key Condo 3.9 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

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

siesta key
3 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 8

Siesta Key Condo 4.3 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

Siesta Key Apartment 4.7 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Apartment Rental Sleeps 5

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Siesta Key Condo 5.0 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

Siesta Key Apartment 4.5 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Apartment Rental Sleeps 6

Siesta Key Apartment 4.4 Star Review

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

Siesta Key
1 Bedroom(s) - 1 Bath(s)
Apartment Rental Sleeps 2

Siesta Key Condo 4.8 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Siesta Key Apartment 5.0 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Apartment Rental Sleeps 4

Siesta Key Cottage 4.0 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Cottage Rental Sleeps 4

Siesta Key Apartment 3.7 Star Review

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

Siesta Key
2 Bedroom(s) - 2 Bath(s)
Apartment Rental Sleeps 6