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Siesta Key Vacation Rentals, Condos & Apartment Rentals.

Book Your Siesta Key Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Siesta Key Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Siesta Key Florida.

Siesta Key Gulf Front Condo

Siesta Key Condo Star 5.0 Star Review

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor and is .......read more

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


Vacation Rental


Luxury Villa: 2 min walk to beach and The Village. Contact me for <30 day stay.

Siesta Key Villa Star 5.0 Star Review

Enjoy a fantastic experience at this prime Siesta Key location, and beautiful Villa. Luxury Villa is across the street from the Siesta Key beach (beach access #5), the top beach in the USA and noted as a top international beach. Villa is also located via a two minute walk to the Siesta Key Village; various restaurants, bars and shopping. No need .......read more

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


Vacation Rental


Beautiful Siesta Key 2-Bedroom Apartment!

Siesta Key Private vacation home Star 4.8 Star Review

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 everyt.......read more

2 Bedroom(s)
2 Bath(s) Sleeps


Vacation Rental


Gulf and Bay Club 102B, Sleeps 4, Lagoon View, Ground Floor, 2 Bedrooms

Siesta Key Condo

Ready to spend twenty-eight days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This ground-floor condo is located in a thirty-two-acre resort community, just steps from the sparkling white-quartz beach deemed the country’s best by the TripAdvisor’s Travelers’ Choice awards.

One of the most luxurious condo communi.......read more

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


Vacation Rental


Great Siesta Key Location with Deeded Beach Access at The Anchorage 308

Siesta Key Condo Star 4.5 Star Review

Great Siesta Key Location at The Anchorage. Deeded Beach Access, Walk to Shopping & Dining!

Spacious 2 bedroom, 2 bath, 3rd floor condo at The Anchorage with private deeded beach access to Crescent Beach. New tile floors, new leather furniture in the living room, new dining set, new SMART TV’s in living room & master bedroom. Split floorpl.......read more

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


Vacation Rental


Prem 2Bed/2Bath Gate House Cottage with private beach access!

Siesta Key Cottage Star 4.8 Star Review

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 Rental


1010-1012 Point of Rocks- Brand new remodel and by the beach!

Siesta Key Private vacation home Star 4.8 Star Review

Beautiful Duplex located 1 house away from beach! Amazing Location! These beautifully decorated duplexes feature all the conveniences of home with a fully equipped kitchen and linens provided. The duplexes sleep 16 and are equipped with a king in the master bedroom, a queen and 2 twins in the guest bedrooms and in 1010 the master features a quee.......read more

6 Bedroom(s)
6 Bath(s) Sleeps 14


Vacation Rental


Coral Breeze | Siesta Home, Heated Pool & Spa, Minutes to Village and Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Introducing Coral Breeze, where your vacation is a breeze! This beautiful 3-bedroom / 2.5 bathroom includes a fully equipped kitchen, private heated pool and spa, spacious outdoor patio, and gas grill. Located less than 1.5 miles from Siesta Key Public Beach Access #2, you\'re able to enjoy the best of both worlds by relaxing poolside or soaking u.......read more

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


Vacation Rental


New Listing! Sea Coast | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home Star 4.8 Star Review

Welcome to Sea Coast! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the p.......read more

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


Vacation Rental


Beautifully Updated Ground Floor at Gulf & Bay Club. Gulf Front Living at it's Finest!

Siesta Key Condo Star 5.0 Star Review

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 Rental


Buttonwood 417 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo Star 5.0 Star Review

**** 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. 3r.......read more

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


Vacation Rental


Siesta Key Beachfront, Updated 2 BR, 2 BA Condo, Sunset Views; Peppertree Bay!

Siesta Key Condo Star 5.0 Star Review

**PLEASE NOTE: I rent to guests only through VRBO. If you\'ve received a quote or information from any other site, it is not legitimate. Please feel to reach out to me through this site with questions.**

Experience Siesta Key resort living at its best at Peppertree Bay! The condo:

• Is located directly on the beach, with gorgeou.......read more

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


Vacation Rental


Poolside Condo minutes from Siesta Key Beach

Siesta Key Condo Star 4.8 Star Review

This bright and relaxing condo includes 2 bedroom (1 King) (1 Full/Twin bunk bed) Full kitchen including dishwasher, coffee pot, basic utensils. Washing/Dryer, Air Conditioning, Wi-fi, 3 TVs with cable in the living room and each bedroom.

From your screened lanai it is only steps to the gated heated pool. Steps from your front door is a co.......read more

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


Vacation Rental


Chinaberry 456 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo Star 5.0 Star Review

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 Rental


Aloha Kai - Unit 4-updated and by the pool!

Siesta Key Cottage Star 5.0 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 parki.......read more

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


Vacation Rental


Siesta Beach House #308 Minute Walk to Beach

Siesta Key Apartment Star 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

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


Vacation Rental


New Listing! Sea Dream | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Welcome to Sea Dream! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the p.......read more

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


Vacation Rental


Sprinkle of Irish charm, beautifully updated, Siesta Dunes 8-205

Siesta Key Condo Star 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

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


Vacation Rental


Siesta Beach House #312 Minute Walk to Beach

Siesta Key Apartment Star 3.9 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

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


Vacation Rental


Cozy Family Condo- Beautiful Newly Renovated 2 Bedroom - Near Siesta Key!

Siesta Key Condo

The Dock Holiday is located at the popular Bay Oaks Condominiums in a beautiful, park-like setting on the intracoastal waterway, where you can watch the sunrise. Spacious and updated, second floor, two-story condo with almost 1400 square feet of living space.

The living room is furnished with a large flat-screen TV, including free WiFi, and .......read more

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


Vacation Rental


New Listing! Sea Angel | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Welcome to Sea Angel! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the p.......read more

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


Vacation Rental


Gorgeous Views for sunsets over Siesta Key from enclosed Lanai.

Siesta Key Apartment Star 4.8 Star Review

Enjoy stunning views of the beautiful white sands of Siesta Beach and gorgeous sunsets from your picture window of this 2 bedroom 2 bath 3rd floor condo.
This family friendly beach view condo has everything you will need for a carefree, comfortable stay in Paradise.
Award winning Siesta Beach is just steps away and a 10 minute walk finds you.......read more

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


Vacation Rental


Chinaberry 414 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo Star 5.0 Star Review

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 Rental


SIESTA KEY! MIDNIGHT COVE 2/2 GULFRONT! BOOKING FOR FALL 2022 NOW!

Siesta Key Condo Star 4.7 Star Review

SOME RESTRICTIONS APPY DUE TO COVID 19.

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 delight.......read more

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


Vacation Rental


Private RENOVATED Villa Paradise with private Beach access 2br/2ba

Siesta Key Villa Star 4.6 Star Review

Newly renovated private villa! Beautiful brand new kitchen with quartz countertops and stainless steel appliances. All new flooring through out and newly decorated!
Be one of the first guests in this newly renovated clean villa.
It\'s like having your own private beach house!!
Photos are the older photos, new photos will be posted soon.<.......read more

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


Vacation Rental


Sunset Royale - 118- Bright and Beachy Across from beautiful Siesta Key Beach!

Siesta Key Apartment Star 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

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


Vacation Rental


Steps to the ⭐ Beach, Short Walk to the Village

Siesta Key Private vacation home Star 4.9 Star Review

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 Rental


Sunset Royale - 206- Close to Beach and Siesta Village

Siesta Key Condo Star 4.8 Star Review

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 Rental


Relaxing Siesta Key Condo

Siesta Key Condo Star 4.9 Star Review

Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or evening cocktail on the balcony with views of the beautiful inter-coastal waterway from your vacation home. Deeded beach access to Siesta Key’s famous Crescent Beach quartz sand beach is just a short stroll across the street; a.......read more

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


Vacation Rental


Siesta Beach House #303, Beautiful updated Unit

Siesta Key Private vacation home Star 4.6 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

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


Vacation Rental


New Listing! CJs on Siesta | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home

Welcome to CJ\'s on Siesta! This group of 6 private units is perfect for large families and groups, with the ability to accommodate up to 24 guests, with 6 bedrooms and 6 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s wo.......read more

6 Bedroom(s)
6 Bath(s) Sleeps 24


Vacation Rental


Crescent Siesta Key #406

Siesta key Condo Star 5.0 Star Review

Crescent Siesta Key is an upscale condo property in the heart of South Siesta Key. My unit is exquisitely appointed for easy luxury and offers a view of the gulf and the world’s finest white sand beaches.

A spacious, vacation-ready condominium awaits you. From fully-equipped gourmet kitchens to spacious living areas with a view of the gulf.......read more

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


Vacation Rental


Charming home on quiet street one block from Siesta Beach.

Siesta Key Private vacation home Star 5.0 Star Review

Comfortable private home on a quiet street one block from Siesta Beach. Lush tropical fully fenced in backyard has a gas grill and comfortable chairs and table, under a shade sail with cafe lights. Walk to the beach or Siesta Village. Fully furnished kitchen has everything you need to feel at home. Enjoy comfortable couches and beds, fast internet.......read more

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


Vacation Rental


New Listing in Bay Oaks, End Unit, Walk to Beach, WiFi, Updated, Pool, Tennis, Complex Fishing Pier

Siesta Key Condo Star 5.0 Star Review

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 Rental


Location. Four bedroom cottage, one block from beach and Siesta Village

Siesta Key Private vacation home Star 5.0 Star Review

Location. Location. Location. Our charming 4 bedroom 3 bath Florida beach cottage, which is over 1800 feet and sleeps 8 with 2 full kitchens and a fully covered porch and large patio in the back unit. Cottage is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United S.......read more

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


Vacation Rental


CA405N - Family Beach Perfection! 2 Bed, 2 Bath Condo with Gulf view; Sleeps 6

Siesta Key Condo Star 4.9 Star Review

This 4th floor unit, with an elevator, is steps from the beach and a short walk to several restaurants, a Tiki bar, an island grocery store and water sports/ boating.

There are two separate bedrooms, each with their own bathroom and flat screen TV. The master bedroom has a King bed and the 2nd bedroom has a queen bed plus a double bed.
<.......read more

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


Vacation Rental


CA705S - COZY, COMFORTABLE CONDO on the #1 beach in the USA>

Siesta Key Condo Star 4.2 Star Review

Bright and cheery, freshly painted, new linens and some new furniture! Brand new Murphy Bed!

Living room has two loveseats and a flat screen TV.

Bedroom has a king bed, large chair and light for reading. Flat screen TV

Lanai has a gulf view of world famous Crescent Beach. Put your toes in its unique 99% quartz sand that has.......read more

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


Vacation Rental


Crystal Sands1107 Exquisite Gulf & Sand Views, Luxury

Siesta Key Condo

1107 is definitely a slice of heaven on Siesta Key. It\'s fresh and new with beautiful new beachy furnishings, new linens, and a full width view deck accessible from every room. Enjoy direct west and north views of the Gulf plus downtown Sarasota views. Take one of three elevators to sugar white quartzite sands & turquoise waters. Designer kitche.......read more

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


Vacation Rental


Our House at the Beach C-111 Newly Remodeled

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 Rental


Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

Siesta Key Cottage Star 4.7 Star Review

Location, location, location. Our charming 3-bedroom 2 bath Florida beach cottage, which is over 1000 feet and sleeps 6, which we call the “Manatee Cottage” is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United States (you will be a 5 minute walk from access 7)........read more

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


Vacation Rental


Our House at the Beach E-404 Sugar Sands Beach View!!

Siesta Key Condo Star 4.3 Star Review

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 includ.......read more

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


Vacation Rental


2,700 sq. ft. home with private pool 200 steps to Crescent Beach - dog welcome

Siesta Key Private vacation home

Seashell Sanctuary

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Happiness is a private pool just 200 steps from the white powdery sands of one of the best beaches in the U.S., Crescent Beach! This single-story slice of paradise is a 2,700 squ.......read more

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


Vacation Rental


Beautiful two bedroom, two bathroom condo with great views.

Siesta Key Apartment Star 4.7 Star Review

Enjoy watching the beautiful sunsets every night from your own private lanai in this two-bedroom, two-bathroom condo. Located at Siesta Beach with Siesta Key\'s famed “Village” a short walk away. This lovely condo has everything you are looking for: fully equipped kitchen, newly renovated bathrooms featuring state of the art toilet system, rain.......read more

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


Vacation Rental


Beautifully Updated Gulf View, 2 Bed, 2 Bath with Loft, Sleeping 6

Siesta Key Condo Star 5.0 Star Review

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 Rental


Siesta Key Condo, on the water , with garage

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 Rental


Tivoli by the Sea-Unit 505 - Gorgeous view with sleep sofa

Siesta Key Apartment Star 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

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


Vacation Rental


Luxurious Waterfront Retreat with bay & city views minutes from Beach

Siesta Key Private vacation home Star 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

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


Vacation Rental


Siesta Key 2-Bedroom Apartment - Anchorage - Beautiful Views!

Siesta Key Condo Star 4.0 Star Review

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. Master bathroom recently renovated and upgraded. Second bedroom has two twin beds, two spacious closets and shared b.......read more

2 Bedroom(s)
2 Bath(s) Sleeps


Vacation Rental


Find the Top Vacation Rentals in Siesta Key, Sarasota Florida.

We have 2,3 or 4 Bedroom beachfront Condo Rentals with ocean view or a Beach House for the entire family. Book Direct Here!

Siesta Key Beach consistently ranked in the top spot as the most beautiful beach in the United States, Siesta Key is the ultimate beach escape. Located close to Sarasota, 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. Vacation Rentals near Siesta Beach, Turtle Beach and Crescent Beach area are the most popular along the barrier island, offering tranquil waters that provide a safe spot for swimming and snorkeling.

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