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.

Aloha Kai - 2 beautful unit and close to pool!

Siesta Key Cottage - 5.0 5.0 Star Review

Fully furnished villa offers living room, dining area, fully equipped kitchen, two bedrooms and 2 bathrooms. 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 parking space directly outside your front door. T.......read more

2 Bedroom(s)
Sleeps 4
Cottage

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Grand Canal Front 3BR/3bath, Pool/Hot Tub, Walk to Beach & Siesta Village

Siesta Key Private vacation home - 4.725 4.7 Star Review

Location, Location, Location. Comfortable 3BR, ground level house, just steps to Siesta Key Beach, #1 Beach in the USA, 2011 & 2014 located on the "Heart" of Siesta Key\'s Grand Canal." Romantics, etc., click on VRBO property "location." Walk, bike, kayak, or take one of the many FREE beach ride services to the beach, Siesta Village shops, dinin.......read more

3 Bedroom(s)
Sleeps 7
Private vacation home

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Beautiful two bedroom, two bathroom condo with great views.

Siesta Key Apartment - 4.66667 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 sho.......read more

2 Bedroom(s)
Sleeps 4
Apartment

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

Siesta Key Condo - 5.0 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)
Sleeps 6
Condo

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Aloha Kai - Unit 49-close to the pool!

Siesta Key Cottage - 4.5 4.5 Star Review

This 2 story Villa is just steps from the largest heated pool on Siesta Key and a few minute walk to our wonderful private beach. Featuring 2 bedrooms upstairs, king bed in the master and 2 twins in the guest room with a full bath to share. This Villa also boasts a spacious living/dining area and fully stocked kitchen on the main floor. Sleeps u.......read more

2 Bedroom(s)
Sleeps 6
Cottage

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

Siesta Key Private vacation home - 4.76923 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)
Sleeps 14
Private vacation home

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New Listing on Siesta Key, Steps to Pool, WiFi/Cable, Outdoor Patio, Sunroom, Carport, King Master

Siesta Key Condo

New Listing in peaceful Polynesian Gardens where you can walk to Crescent Beach on Siesta Key! Just a 12 minute walk to sink your toes in the white powder quartz sands of Crescent Beach! Relax every evening sitting in a beach chair under an umbrella with a glass of wine (ok, plastic!) to watch an incredible Gulf of Mexico sunset!! You won’t be disa.......read more

2 Bedroom(s)
Sleeps 4
Condo

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New Listing! The Coral Reef | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home

Welcome to The Coral Reef! This group of 3 private units is perfect for families and groups, with the ability to accommodate up to 12 guests, with 3 bedrooms and 3 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-ren.......read more

3 Bedroom(s)
Sleeps 12
Private vacation home

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

Siesta Key Condo - 4.25 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)
Sleeps 6
Condo

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Siesta Key Beach View Condo New Stainless Steel Kitchen Appliances

Siesta Key Condo - 4.96667 5.0 Star Review

Looking for a little get away at the Beach? Well, you’ve found it! This recently updated condo features two bedrooms and one full bath which puts you in the perfect location steps away from the world-famous quartz sand of Siesta Key Beach. There is no need to worry about parking, you are a one minute walk to the beach. This 4th floor condo has a co.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Top in Siesta Village at Best Beaches, Food & Entertainment! Casa Van Lopik.

Siesta Key Private vacation home - 4.9 4.9 Star Review

A Gertrude Rentals property.  In the Siesta Village just a short walk to Siesta’s best beaches and sure to provide a combination of fun and rejuvenation you won\'t find in other getaways!  Casa Van Lopik is 100% private with two large 3BR units capable of accommodating up to 20, and a lush tropical indoor/outdoor patio lounging and dining area.  It.......read more

6 Bedroom(s)
Sleeps 22
Private vacation home

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Luxury penthouse unit w/stunning views, open floor plan, & private beach access

Siesta Key Condo

This 2 Bed/2 Bath boasts gorgeous bay views, high-end finishes, and a spacious layout with cathedrals ceilings. Updated kitchen with stainless steel appliances, in-unit washer/dryer, full sleeper sofa and 3 TVs.

If you are looking for a luxury getaway with an unbeatable location this unit has it all!

Exclusive amenities include:read more

2 Bedroom(s)
Sleeps 6
Condo

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Bay Isle Bliss | LIMITED OFFER: Book 4 nights get 3 nights free!

Siesta Key Private vacation home - 4.75 4.8 Star Review

LIMITED OFFER: Book 4 nights get 3 nights free! Valid for vacation dates now through 12/15/22. Contact us for more details!

Bay Isle Bliss is a newly updated, single-family home residing on Siesta Key\'s north end. Three bedrooms and two bathrooms can accommodate up to 8 guests alongside luxury amenities including a private, heated pool and.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Casa Mar - 50- Ground floor unit in Gulf side Complex- studio!

Siesta Key Apartment - 4.42222 4.4 Star Review

This studio condo is approx 420 sq feet and offers a king size bed. Play tennis or shuffleboard, then bask in the sun by the swimming pool located steps from your unit. Stroll down palm lined walkway that lead to Siesta Key\'s fine white quartz sand and enjoy one of Florida\'s spectacular sunsets. Lounge chairs are conveniently located on the beach.......read more

Studio
Sleeps 2
Apartment

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

Siesta Key Private vacation home - 5.0 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)
Sleeps 8
Private vacation home

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Sun Sea Terrace | Siesta Key Penthouse, Located Short Walk to Beach and Village!

Siesta Key Private vacation home - 5.0 5.0 Star Review

This luxurious 4 bedroom/3.5 bathroom penthouse is one block from Siesta Key Village and 2 blocks from Siesta Key Beach, voted the #1 beach in the USA! Sun Sea Terrace features two living rooms, 6 balconies on multiple levels, and a private roof top space with views of the Gulf of Mexico and Siesta Key Village. Sun Sea Terrace is the ideal vacation.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Slice of Beach Paradise | Private Wraparound Balcony with Amazing Gulf Views

Siesta Key Private vacation home - 4.0 4.0 Star Review

Beach Road Condo Unit 2

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

Perched by the shoreline, this 3BR/2BA townhome is a slice of beach paradise. With the Gulf just a 2-minute walk away, enjoy the stretches of sugar-white sand and turquoise .......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Spacious 2Bed/ 2Bath Beachfront Town Home!!

Siesta Key Private vacation home

DIRECTLY ON NUMBER ONE RATED BEACH IN THE USA SIESTA BEACH !!! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Beachfront home on Siesta Key Sunset Point. Siesta Key Beach is the number one rated beach in the USA. Walk out of your fro.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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

Siesta Key Condo - 5.0 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)
Sleeps 6
Condo

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

Siesta Key Condo - 4.33333 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 e.......read more

2 Bedroom(s)
Sleeps 6
Condo

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

Siesta Key Private vacation home - 5.0 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

Studio
Sleeps 4
Private vacation home

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

Siesta Key Condo - 4.69565 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)
Sleeps 6
Condo

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Siesta Key 4 Bedroom, Walk to Siesta Key Beach in 7 mins, Canal Home, Heated Splash Pool, WiFi, BBQ

Siesta Key Private vacation home - 5.0 5.0 Star Review

Upscale Spanish Mediterranean style beautiful custom home on the canal with a private area to launch a kayak, walk to Siesta Key Beach, be able to take a dip to cool off in your own private splash pool and able to bring the whole gang!? It\'s all here waiting for you on Siesta Key, Fl in this gorgeous custom home. This is a large 4 bedroom 3.5 ba.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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5 Star LUXURY RETREAT on BEACH ROAD, SIESTA KEY BEACH, New POOL

Siesta Key Private vacation home - 4.90909 4.9 Star Review

One of the nicest private homes on Siesta Key Beach. We have the highest 5 star rating on Siesta Key. See Vrbo 802548 for more reviews of this home - . Stunning and spacious on Beach Road right across the street from Beach Access 10 (ranked number one Beach in US.) Please note that our vacation home consists of two units. This listing\'s pri.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Tivoli by the Sea-Unit 407 - Gorgeous View of the Gulf

Siesta Key Condo - 4.57143 4.6 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, and a queen & twi.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Gorgeous Views for sunsets over Siesta Key from enclosed Lanai.

Siesta Key Apartment - 4.8 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)
Sleeps 6
Apartment

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Chinaberry 913 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo - 5.0 5.0 Star Review

Brand New to Rental Program! Recently refurnished and re-decorated! Ground-level, bay front, 2BR/2BA that sleeps 6. Full Water & Bay Views! King Bed in Master, 2 Doubles in the Guest Bedroom. Large walk in Shower in Master Bath with dual-sink counter top. Walk-in shower in Guest Bathroom in the hallway. Glass and Screened Lanai perfect for relaxin.......read more

2 Bedroom(s)
Sleeps 6
Condo

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

Siesta Key Condo - 5.0 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)
Sleeps 6
Condo

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Hidden Treasure - Quiet Neighborhood, Private Heated Pool, Gas Grill, & More!

Siesta Key Private vacation home - 5.0 5.0 Star Review

Escape to Siesta Key\'s "Hidden Treasure," where you\'ll experience a bright and cheerful retreat for families looking for peaceful serenity. The main 2 bedroom/ 2 bath residence opens up to large, luxurious pool courtyard that connects to a private Casita with 2 generously sized bedrooms and additional full bath. The screened in courtyard features.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Our House at the Beach 222, Sleeps 4, 2 Bedroom, Tennis, Heated Pool

Siesta Key Condo - 4.51515 4.5 Star Review

There\'s plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! The huge sectional sofa faces our new HDTV with DVD player, so anytime you need a little downtime from all the outdoor fun, settle in with your favorite movie, a bowl of popcorn, and frosty drinks. The kitchen.......read more

2 Bedroom(s)
Sleeps 4
Condo

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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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