Siesta Key Beach Florida Vacation Rentals, Hotels & Resorts

Search for Vacation 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 Next Vacation Rental Directly Online Here and Save!

We have partnered with a major provider of vacation rentals, 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

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 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 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 Rental

Siesta Key apartment

Island House Beach Resort 9S

Island House Beach Resort - 9 South

Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft., non-carpeted and has a large living area, dining area, fully equipped kitchen, all appliances, lanai. It has a king, 2 twi ....

2 Bedroom(s) 2 Bath(s) Apartment - Sleeps 4
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 condo

Bay Oaks, 4th floor corner - elevator

Gulf View w/ Short Walk to Beach, Fishing Pier and Tennis

Bay Oaks, 2 Bedroom, 2 Bath, Sleeps 4. Enjoy this beautiful updated two bedroom, two bath condo which has all of the amenities you are looking for in a luxurious and relaxing atmosphere. Bay Oaks is set among tropical foliage and beautiful wal ....

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

View Rental

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 Rental

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

View Rental

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 Rental

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 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

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 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 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

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 Rental

Siesta Key house

Seahorse Cabana - 1106

Seahorse Cabana - One of The Cottages on the Key

Welcome to the Seahorse Cabana! Please Note: Sleeps 8: K, K, 2T, QAB (queen air bed) These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If on ....

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

View Rental

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 Rental

Siesta Key condo

Sweet Siesta Condo at Beach

CONDO ON SIESTA KEY, 2 QUEEN BEDS, WALK OVER TO #1Beach in America, Only $75

This renovated Condo is right on Siesta Key, which is located in Sarasota Florida. Don't just stay in Sarasota or "near Siesta Key", stay right on Siesta Key, where you can Walk right over to Siesta Key Main Beach, again rated the #1 Beach in Americ ....

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

View Rental

Siesta Key house

324 Avenida Madera, Siesta Key

Island Home in Paradise!!

Newly remodeled, single family home, 3 bedrooms, 2 baths, enclosed screened-in 27 x 13 heated outside pool(set to 82 degrees) with sunshelf...have dinner/cocktails outside in pool on sunshelf!! Short walking distance to 15 great restaurants, 12 bars, ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
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 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

View Rental

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 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 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 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 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 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 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 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 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


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