Siesta Key Beach Florida Vacation Rentals, Hotels & Resorts

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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Siesta Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Siesta Key cottage

Honey Mango Cabana - 1144E

Honey Mango Cabana - One of The Cottages on the Key

Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of "Mango Manor," which is comprised of the two separate cabanas, Honey and ....

2 Bedroom(s) 1 Bath(s) Cottage
Siesta Key, FL

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Siesta Key apartment

SIESTA BEACH 3 BEDROOM

Beautiful Apartment with Ocean Views, Includes beach towels and chairs!

Check out my other amazing VRBO property reviews: Vrbo.com/4802815 ! Location, location, location! This beautiful apartment has been decorated to a home cozy feel. Newly done oversize balcony has most spectacular view on the Gulf and Beach, so you ....

3 Bedroom(s) 2 Bath(s) Apartment - Sleeps 6
Siesta Key, FL

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Siesta Key villa

Island House Beach Resort V27

Island House Beach Resort - Villa 27

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 park ....

2 Bedroom(s) 2 Bath(s) Villa - Sleeps 6
Siesta Key, Fl

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Siesta Key house

Sea Shell Casita - 1121

Sea Shell Casita - One of The Cottages on the Key

The Sea Shell and Sea Wave are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: These units [Sea Shell & Sea Wave] can be rented separately. Combi ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key cottage

Siesta Key Beach Cottage

Siesta Key Beach Cottage Across The Street From #1 Beach In USA

The Siesta Key Beach Cottage is located right on Beach Rd directly across the street from the #1 Beach in the USA. Walk out the front door and walk across the street to beach access #7 and you are on the white powder Beach of Siesta Key. You can loo ....

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

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Siesta Key house

Sandy Shore

4 Bedroom Key West Style Home W/ Heated Pool, Close to Village and Beaches

Stay at this large Key West style Siesta Key vacation rental home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool and Jacuzzi hot tub. Located on a quite street just 1 mile from Siesta Key village pu ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key apartment

SV 1BR

1BR - Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Village

SEASIDE VILLAS - Deluxe Garden Apartment of Siesta Key Townhouse Vacation Rental - With Heated Pool Located in the Heart of Siesta Key Village, Sarasota, FL - Short Walk to Crescent Beach SEASIDE VILLAS: This Siesta Key one bedroom garden apartment ....

1 Bedroom(s) 1 Bath(s) Apartment
Siesta Key, FL

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Siesta Key condo

Siesta Dunes 1-406

SIESTA DUNES 1-406 LUXURY CONDO WITH A GREAT VIEW!

Located on American’s #1 white sand Crescent Beach, this condo has a great ocean view from the top floor of Building 1! This fourth floor, non-smoking unit has cathedral ceilings and is beautifully decorated. An elevator and laundry room are just s ....

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

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Siesta Key condo

Harbor Towers

Newly Renovated & Modern, Wifi, Gulf Facing Harbor Towers, 3 bedroom with den

Newly remodeled, modern and beautiful 3 bedrooms, plus a den, 3 full bath condo right on Siesta Key, in a complex overlooking the intracoastal waterway and close to the beach!! Fabulous powdery white sands of Siesta Key Beach are just a short s ....

3 Bedroom(s) 3 Bath(s) Condo
Siesta Key, FL

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Siesta Key condo

Siesta Heron 6 / Sunset Suite

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

This is a spacious studio style two bedroom unit furnished with king-size bed and queen sleeper sofa downstairs and queen bed upstairs Accommodating up to 6 persons. The downstairs bathroom is equipped with tub/shower combo. While the upstairs offers ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key house

Latitude Adjustment - 461

Latitude Adjustment - One of The Cottages on the Key

Welcome to Latitude Adjustment! This breathtaking 4 bedroom, 4 bathroom home is perfectly situated between America's #1 beach in the world and Siesta Key's famous North Village! You will not be able to ask for more as you drive up to this tropical oa ....

4 Bedroom(s) 4 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Coconut Grove

Coconut Grove - One of The Cottages on the Key

Welcome to Coconut Grove! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 16, a private heated pool, and quite literally in the heart of Siesta Village! ....

6 Bedroom(s) 6 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Casita Playa - 1139W

Casita Playa - One of The Cottages on the Key

Welcome to Casita Playa of Playa y Blanca. This single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimmin ....

2 Bedroom(s) 1 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key condo

FC 3BR

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

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 Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstr ....

3 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key villa

Vacation Home

Beach Goers Paradise! Siesta Key 2/2 Condo

This charming villa allows you to enjoy all that beautiful Siesta Key has to offer. The white sands of Crescent Beach are just across the street. You may enjoy swimming in the Olympic size pool at Aloha Kai. Spend the evenings relaxing in your privat ....

2 Bedroom(s) 2 Bath(s) Villa - Sleeps 4
Siesta Key, FL

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Siesta Key condo

Siesta Harbor Condominium

Siesta Key Condo....Relax, enjoy and feel at home......

Come vacation in this beautiful one bedroom, two bath, third floor condo. Siesta Harbor is an over 55+ community located directly across the street from America's #1 beach. Deeded access to Crescent Beach makes this super convenient. The condo also h ....

1 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Siesta Key, FL

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Siesta Key condo

Midnight Cove II Bldg 6

Private Beach Access, Gulf Views, Wifi/Cable, Pool, Renovated Condo With Amenities, Tennis

Enjoy your vacation in this beautifully renovated two bedroom 1.5 bath condo that sleeps 6. Step into the unit and immediately notice the warm open feel, the beautifully tiled floors and the sweeping panoramic views of an inlet off of the intra ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key townhome

Updated Bayside Townhouse

Updated Townhouse! Private access to Beach. Enjoy Tennis, Heated Pools, Fishing

Across the street is our Private Access to one of the BEST beaches - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! Gulf & Bay Club Bayside is a gated resort community of Key West style Town Homes all with ....

2 Bedroom(s) 2 Bath(s) Townhome - Sleeps 6
Siesta Key, FL

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Siesta Key house

Vacation Home

Siesta Waterfront Retreat

Beautiful, spacious home away from home awaits for you. Water front house, right on the canal, only one bridge away from the ocean, it is located in a very quiet dead end road, which makes it very private and peaceful. Here, you are minutes away to ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 12
Siesta Key, FL

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Siesta Key house

Winding Way Siesta Key

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 un ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key condo

FC 2BR

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks 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 b ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key condo

CA 2BR Front Corner

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 ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key house

Casita Morning Star - 6920

Casita Morning Star - One of The Cottages on the Key

Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decade ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key condo

The Terrace

Penthouse with Extraordinary Island Views, Directly on the Beach, Heated Pool

Siesta Key has come to be known around the world for is top rated beaches. One of the reasons it is continually rated #1 beach in America is of course it's extraordinarily soft white sands. Another main component which makes Siesta Key and its beache ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key townhome

Beach Cove

Walk to the #1 Beach in America, Offers Heated community Pool, Free Wi-Fi

Siesta Key has been named America's #1 beach time and time again. Experience fun in the sun like never before at this two-story townhome style condo located just a few hundred feet from the private access beach. Towards the front of the community gue ....

2 Bedroom(s) 3 Bath(s) Townhome
Siesta Key, FL

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Siesta Key apartment

SIESTA BEACH APARTMENT

Prime location on Siesta Beach, Includes beach towels and chairs!

This apartment has been decorated to make feel like home with very cozy atmosphere. Has beautiful over sized closed in lanai. You can enjoy morning coffee and breakfast or just relax a in the afternoon or evening breathing fresh air. Ideal locatio ....

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

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SIESTA KEY condo

Beach Condo,The Calm @ Siesta!

Siesta PREMIER LOCATION and View just can't be beat!!!

This new vacation rental is the 'Calm of Siesta', as you enter with a full view of the Gulf of Mexico and Siesta Key Beach. The property has just been newly transformed to accommodate our guests best welcome to Siesta. The property is equipped with a ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 5
SIESTA KEY, FL

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Siesta Key condo

Siesta Beach House

Fabulous Siesta Beach House

Our place on the #1 Siesta Key beach is near to Siesta Key village, Downtown Sarasota, Lido Key, St Armand s circle and LongBoat Key. You’ll love our place because of the location, and the ambiance. LITERALLY a few steps to private Crescent beach ( ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Siesta Key, FL

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Siesta Key condo

Siesta Heron 3 / Captiva

Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key

This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa in the living room accommodating up to four persons. The living room is furnished with a 40" flatscreen TV with HD programing. The ....

1 Bedroom(s) 1 Bath(s) Condo
Siesta Key, FL

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Siesta Key house

SiestaKey, house- TopWorld Bch

ISLAND GLASS - HOUSE, AVAILABLE

THIS IS A HOUSE W/ GARAGE- PRIVATE POOL, W/ FREE ...KITCHEN, BATH, LAUNDRY CONDIMENTS.... BELOW MARKET... NOT A CONDO....Go to earthcam .com view siesta key beach for yourself. It is lovely outside today. WE HAVE THE BEST GUEST!.... PLEASE READ. ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Siesta Key, FL

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Find Affordable Siesta Key Beach Hotels & Vacation Rentals

Plan your Siesta Key Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Siesta Key, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.


Vacation Rentals Nearby Tampa Bay Destinations

Find nearby vacation rentals and some of the Best Hotels with cheap rates in Siesta Key, FL for you visit to the area, all a short drive to Siesta Key, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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