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....

Best Rental Prices 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 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

The Pearl by the Sea - 5258

The Pearl by the Sea - One of The Cottages on the Key

Welcome to The Pearl by the Sea. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring a private heated pool and spa, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. You hav ....

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

View Rental

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 Rental

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 Rental

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

View Rental

Siesta Key apartment

Island House Beach Resort 5N

Island House Beach Resort 5 North

Island House Beach Resort - Crescent Beach, Siesta Key. Gulf Front Unit, 3rd Floor, Panoramic Views. This luxury apartment is 1300 sq. ft. non-carpeted and is 2 bedrooms, 2 bathrooms. It has a large living area, dining area, fully equipped kitchen, ( ....

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

View Rental

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 Rental

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 Rental

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

View Rental

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 Rental

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

View Rental

Siesta Key house

Seagrove

NEW Private Siesta Key Vacation Rental Home W/ Heated Pool on Quiet Street

Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where ....

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

View Rental

Siesta Key house

536 Canal Road

Luxurious Vacation Home, Salt Water & Heated Pool, Partial Ocean Views

Welcome to Paraiso de Siesta, newly built in 2013 and one of the most Magnificent Vacation homes on Siesta Key. From the moment you walk into the the entry way, your eyes span the openness of the well designed space that leads to the balcony looking ....

4 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 11
Siesta Key, FL

View Rental

Siesta Key condo

Siesta Dunes 5-303

Siesta Dunes 5-303, Come enjoy our little piece of Paradise!

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 ....

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

View Rental

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 Rental

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

View Rental

Siesta Key house

Sandy Cabana - 1104N

Sandy Cabana - One of The Cottages on the Key

Welcome to the Sandy Cabana! Please Note: Sleeps 8- K, K, Q, QAB These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If one unit is not availabl ....

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

View Rental

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 Rental

Siesta Key apartment

Siesta Key Guest House (2b5)

2 Bedroom #5 - Spacious vacation rental unit

This unit has 2 bedrooms. Each bedroom has attached bathrooms. The living area has a wall mounted flat screen with Roku. There is a private enclosed patio with table and chairs for 4. You can enjoy the breeze from there. The village is just a ....

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

View Rental

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

View Rental

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

View Rental

Siesta Key studio

Large Private Studio Apartment

Large & Comfortable Private Studio with Separate Entrance - Walk to Village

Relax, get away and enjoy Siesta Key's laid back lifestyle! Surrounded by lush, tropical vegetation, and nestled in a quiet residential neighborhood, you’ll love this comfortable, 500 square foot, private Studio Apartment. The Studio accommodates 2 ....

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

View Rental

Siesta Key cottage

Mermaid's Retreat

Mermaid's Retreat on Siesta Key, #1 beach in the US!

This newly renovated studio cottage is on canal water and a casual walk to famous USA #1 Siesta Beach. It comfortably accommodates two guests with a futon option for a third. Mermaid's Retreat is the perfect location for your Florida Vacation. You ....

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

View Rental

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 Rental

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 Rental

Siesta Key house

Casita Sol - 1137W

Casita Sol - One of The Cottages on the Key

Welcome to Casita Sol of Sol y Mar. This COMPLETELY RENOVATED, single level (2 Bedroom / 1 Bathroom - 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 setti ....

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

View Rental

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

View Rental

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 Rental

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 Rental

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

View Rental

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 Rental


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