Siesta Key Beach Florida Vacation Rentals, Hotels & Resorts

Search for Vacation Rental Homes or Hotels

           
Best Prices Booking


Vacation Places To Stay We have chosen to partner with Booking.com to offer travelers the best choices for vacation properties - No Booking Fees, Last Minute Room Availability, 2,146,000+ hotels, apartments, villas, condo rentals and more....

Rentals in Siesta Key, FL

Don't know Where To Stay? Select your destination and search for discount accommodations.

If you don't see your travel destination, just type it in the box and search for hundreds of Hotels, Resorts, Motels, Homes, Villas or Condos and more!

Cheap Hotels Siesta Key, FL

Trying to save money on your vacation? VacationPlacesToStay.com has great deals and low prices on vacation rentals & hotels, Best Price Guaranteed.

Save when you book directly online for last minute deals with 3 to 5 Star Resorts, Inns, Hotels and more!


Search hundreds of Vacation Rentals, Condos and Homes in Siesta Key Beach, Florida

Book Your Vacation Homes Directly Online Here and Save!

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 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

View Vacation Home

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

View Vacation Home

Siesta Key villa

Island House Beach Resort V37

Island House Beach Resort - Villa 37

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 ki ....

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

View Vacation Home

Siesta Key cottage

Juicy Mango Cabana - 1144W

Juicy Mango Cabana - One of The Cottages on the Key

Welcome to the Juicy Mango Cabana! This beautiful and vibrant 2 bedroom, 2 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, Juicy and ....

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

View Vacation Home

Siesta Key house

Home Away From Home on Siesta

Stay in Siesta Key Village and Walk to the Beach!

This charming tropical 1,320 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. Newly renovated and with all new furniture this private beach home will have you relaxed from the ....

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

View Vacation Home

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

View Vacation Home

Siesta Key condo

Beach front Condo

Direct Siesta Key Beachfront condo!

Our beautiful fully remodeled condo is located directly across the street from world famous Siesta Key Beach! Whether you would like to put your toes in the crystal white sands of the beach or enjoy our large heated pool you will be in paradise! Enjo ....

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

View Vacation Home

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

View Vacation Home

Siesta Key apartment

Island House Beach Resort 14S

Island House Beach Resort 14 South

Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condos offers a view of the palm trees, white sand and turquoise waters of th ....

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

View Vacation Home

Siesta Key house

Casita Blanca 1139E

Casita Blanca - One of The Cottages on the Key

Welcome to Casita Playa of Playa y Blanca. This COMPLETELY RENOVATED, 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 c ....

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

View Vacation Home

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

View Vacation Home

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

View Vacation Home

Siesta Key condo

LaSiesta Condominiums Beach RD

Inquire about discounts! Just steps to the #1 Siesta Key Beach, Renovated 2017

This Completely renovated in 2017 Two Bedroom, One Bath condo with a view of the beach is just steps to the white, powdered-sugar sand of Siesta Key . Here at La Siesta Condominiums you also have easy access to Siesta Village and it's numerous resta ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 5
Siesta Key, FL

View Vacation Home

Siesta Key house

Sand Dollar Cottage - 910

Sand Dollar Cottage - One of The Cottages on the Key

Welcome to the completely remodeled, and newly furnished Sand Dollar Cottage! This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy the peacefulness of a large h ....

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

View Vacation Home

Siesta Key apartment

Island House Beach Resort 6N

Island House Beach Resort 6 North

Island House Beach Resort!! Siesta Key Florida. This 2 bedrooms, 2 bath unit is 1300 sq. ft. and is located on one the finest beaches in Florida. It has a large living area, dining area, 2 lanais, central heat/ac, fully equipped kitchen, ( all applia ....

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

View Vacation Home

Siesta Key condo

Our House at (Siesta) Beach

Direct Access to Splendid White Sands at Siesta Beach, Rated Best Beach in USA

Enjoy nature and culture at its best! Light-filled, two bedroom, two bath, corner unit condo has 2 walls of glass sliders that open onto two large furnished balconies. You will be just steps from Siesta Beach - rated one of the best beaches in the wo ....

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

View Vacation Home

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

View Vacation Home

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

View Vacation Home

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

View Vacation Home

Siesta Key house

Pura Vida Oasis - 350

Pura Vida Oasis - One of The Cottages on the Key

This spectacular bright cheerful, canal front cottage with a heated pool & spa has 5 bedrooms and 3 baths and it can sleep a total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area awaiting on your right ....

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

View Vacation Home

Siesta Key condo

Siesta Heron 5 / Key Lime

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

This is a two bedroom two bathroom unit furnished with king-size bed in one private bedroom, two twin-size beds in the other private bedroom, and sleeper sofa in the living room accommodating up to 6 persons. There are two bathrooms one with shower o ....

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

View Vacation Home

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

View Vacation Home

Siesta Key house

Sea Esta - 5319 (L)

Sea Esta - One of The Cottages on the Key

This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? Siesta Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta o ....

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

View Vacation Home

Siesta Key house

Casa De Mariposa

Casa De Mariposa - One of The Cottages on the Key

Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to includ ....

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

View Vacation Home

Siesta Key condo

Siesta Heron 4 / Sand Dollar

Hidden Paradise on Lakefront Property Among Tropical Landscape 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

View Vacation Home

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

View Vacation Home

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

View Vacation Home

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

View Vacation Home

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

View Vacation Home

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

View Vacation Home


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.

© Reservations Direct, Inc. - Vacation Rentals, Resorts & Hotel Accommodations

About Us - Privacy - Top Destinations - Best Vacation Spots - Car Rentals