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.

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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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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BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

siesta key Condo - 4.88 4.9 Star Review

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

Top beachfront unit at Fisherman\'s Cove!! Fisherman\'s Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of t.......read more

3 Bedroom(s)
Sleeps 8
Condo

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Aloha Kai - Unit 39-beautifully updated!

Siesta Key Cottage - 4.0 4.0 Star Review

Fully furnished villa offering living room, dining area, fully equipped kitchen, two bedrooms and one bathroom. 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.......read more

2 Bedroom(s)
Sleeps 4
Cottage

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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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OVER 180 DEGREE VIEW OF THE BEACH AND GULF!!!

Siesta Key Condo - 4.86538 4.9 Star Review

Location, view & value. This is the best location, the best value, and absolutely the most stunning view in Siesta Key. There’s even a nice view of Sarasota Bay and the mainland from your kitchen window. Views galore from every room (except for 1 closet).

This 11th floor condo has both panoramic views of the Gulf of Mexico and the beach.......read more

2 Bedroom(s)
Sleeps 5
Condo

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Welcome to Paradise! Pet Friendly! Walk to acclaimed Siesta Beach!

Siesta Key Private vacation home

**** APRIL IS THE BEST MONTH TO BE IN PARADISE !!! ****
Ahhh, welcome to Paradise — where sunny, warm weather embraces your soul. Snow, ice, rain, gray days got you down? Cheer up! Come and see why spring is the best time of year to be in Siesta Key, Florida. Enjoy this private 3 bedroom, 2 bath house on Palm Island, the h.......read more

3 Bedroom(s)
Sleeps 9
Private vacation home

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Private villa, 7 min walk to beach, restaurants, grocery

Siesta Key Villa - 4.90909 4.9 Star Review

Amazing private location, steps away from all the action. Seven minute walk to beach, restaurants, grocery store, and boat rentals. This place will feel like your home away from home. Recently renovated with all new furnishings, including a large, fully stocked kitchen and 65-inch TV in living room. Enter this single family, one story, 1200 SF hous.......read more

2 Bedroom(s)
Sleeps 7
Villa

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Spectacular Crescent Beach Siesta Key Gulf Views. NonSmoking Condo

Siesta Key Condo - 4.96667 5.0 Star Review

Location, Location, Location! We are located directly on the Gulf of Mexico on the best part of Crescent Beach. #1 in the world by National Geographic Magazine. #2 in America\'s Best Beaches-2012\' by Dr. Stephen Leatherman, AKA Dr. Beach.
Welcome to our spacious condominium, minutes from great shopping, restaurants, and more! Enjoy this beauti.......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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Top Location on Siesta Key! Private Gate into Village! No car required!

Siesta Key Private vacation home - 5.0 5.0 Star Review

A Gertrude Rentals offering.  Two properties in the Siesta Key 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!   This package can accommodate up to 12 people and includes a 3BR unit and an additional studio apartment two for down each located near the be.......read more

4 Bedroom(s)
Sleeps 12
Private vacation home

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NEWLY REMODELED! On World Famous Crescent Beach

Siesta Key Condo - 4.61538 4.6 Star Review

Condo was fully remodeled in the summer of 2020 complete with beautiful new flooring. Kitchen was completely redone with new cabinets, quartz countertops, and all Stainless Steel appliances.

TV\'s in both bedrooms
Two new Recliners in Living Room
55" HD LED TV with DVR and Blu-ray Player in LR
King bed in Master .......read more

2 Bedroom(s)
Sleeps 6
Condo

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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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Pet-friendly condo a short walk from private beach & fishing dock on bay

Siesta Key Condo

Get your second wind at A Second Wind! Roomy, quiet and comfortable third-floor condo at beautiful Island Reef. Beach-to-bay complex on the peaceful side of Siesta Key with a pool view. Our private Gulf beach, pools and bay are not crowded at all. Two heated pools, tennis courts, pickleball and sauna. The private beach is just a five-minute walk ac.......read more

2 Bedroom(s)
Sleeps 4
Condo

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Siesta Dunes Beach 201, Completely Renovated, 2 Bedrooms, Sleeps 6, Spa, Large H

Siesta Key Condo - 4.25806 4.3 Star Review

This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout. Decked in pure tropical style, Siesta Dunes Beach 201 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, .......read more

2 Bedroom(s)
Sleeps 6
Condo

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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! CJs on Siesta | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home

Welcome to CJ\'s on Siesta! This group of 6 private units is perfect for large families and groups, with the ability to accommodate up to 24 guests, with 6 bedrooms and 6 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 wo.......read more

6 Bedroom(s)
Sleeps 24
Private vacation home

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Jamaica Royale 91, 3 Heated Pools, 2 Bedrooms, WiFi, Sleeps 6

Siesta Key Condo - 3.98485 4.0 Star Review

In this handy ground-floor condo, you\'re just a short walk away from gorgeous Crescent Beach, the jewel in Siesta Key\'s crown. Enjoy laid-back beach living, from the open-air patio to the sun-washed living room!

Jamaica Royale 91 redefines "easy." No stairs, no hallways, no fuss -- just walk right up and you\'re in! The patio will lure you.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Gulf and Bay Club 204C, Beach Front, Spa, 3 Pools, Sleeps 6, 2 Bedroom, Gym

Siesta Key Condo

Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf and Bay Club 204C, you\'ll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. And the use of resort amenities is included! Twenty-eight-day minimum stay required.

Gulf and Bay Club 204C is available for stays .......read more

2 Bedroom(s)
Sleeps 6
Condo

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1 Bedroom Point of Rocks Road-next to the beach!- 3 NIGHT MINIMUM

Siesta Key Apartment - 4.54545 4.5 Star Review

Beautiful 1 bedroom unit located 1 house away from beach! Amazing Location! This beautifully decorated unit features all the conveniences of home with a fully equipped kitchen and linens provided. Enjoy the tropical pool or walk just a short distance to the beach. Point of Rocks is a small, quiet, residential neighborhood on Siesta Key, a few block.......read more

Studio
Sleeps 4
Apartment

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Relax in Style at Bay Oaks in Siesta Key - Watch Dolphin in the Bay - Fish from the Pier. Unit E81

Siesta Key Condo - 3.93333 3.9 Star Review

Relax in Style at Bay Oaks in Siesta Key - Watch Dolphin in the Bay, Fish from the Pier!

Nicely furnished ground floor condo located in the popular Bay Oaks resort on Siesta Key. Covered parking just steps from the unit. Living room has comfortable leather seating, with a queen sleeper sofa for additional sleeping. Both bedrooms have en-suit.......read more

2 Bedroom(s)
Sleeps 6
Condo

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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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Beachfront Resort Style Living - Siesta Beach

Siesta Key Condo - 5.0 5.0 Star Review

**NEWLY REMODELED KITCHEN -- UPDATED FLOORS AND BATHROOMS** Come enjoy luxurious resort style living in this beautiful third floor end unit. The Gulf and Bay Club is the perfect place to relax and enjoy the world famous sands of Siesta Beach. From the moment you walk through the door, you are greeted with sweeping views of immaculate manicured club.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Steps from Siesta Village and the Beach

Siesta Key Condo - 4.87013 4.9 Star Review

100% REFUND IF YOU NEED TO CANCEL - Due to Covid, I am offering a full refund on all cancellations up until the day of trip. I understand that committing to a vacation is much more difficult with all the uncertainty these days and I want to make the process as easy as possible for my guests.

Thanks for viewing our listing. Our condo is loca.......read more


Old World Florida at its Best

Siesta Key Cottage - 5.0 5.0 Star Review

Extremely comfortable 2 bedroom, 2 bath cottage on the grand canal. Enjoy your morning coffee on the dock, breakfast in the screened lanai or afternoon relaxation poolside. There is a peaceful park in front and it\'s a great neighborhood for long evening strolls. The number one beach in the USA is only a four minute walk, and the nightlife and res.......read more

2 Bedroom(s)
Sleeps 2
Cottage

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Our House at the Beach C-220 Perfect Getaway!

Siesta Key Condo - 4.0 4.0 Star Review

This completely renovated and luxurious Lake House townhome directly adjacent to America\'s famed #1 beach - Siesta Beach, offers a spacious bi-level layout that includes separate dining and living rooms with Brazilian cherry hardwood floors. The eat-in kitchen is fully stocked with pots, pans, dishes, and flatware and a suite of stainless steel ap.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West style beach cottage JUST STEPS from #1 SIESTA KEY BEACH!

Siesta Key Cottage - 4.94118 4.9 Star Review

**PLEASE do NOT request to book before contacting hosts. USE "Contact Host button" (blue letters under owners photo on right) BEFORE requesting to book so we can assure this special spot is a good fit for you.**
NO dogs over 20 pounds and ONE dog only. NO more than 2 guests with ONE car.
LOCATION!! Just steps to beach access #7 and a block f.......read more

Studio
Sleeps 2
Cottage

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Gulf and Bay Club 102B, Sleeps 4, Lagoon View, Ground Floor, 2 Bedrooms

Siesta Key Condo

Ready to spend twenty-eight days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This ground-floor condo is located in a thirty-two-acre resort community, just steps from the sparkling white-quartz beach deemed the country’s best by the TripAdvisor’s Travelers’ Choice awards.

One of the most luxurious condo communities o.......read more

2 Bedroom(s)
Sleeps 6
Condo

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A Private Secluded Retreat In Great Neighborhood -Sleeps 8 Near Beach

Siesta Key Private vacation home - 4.94737 4.9 Star Review

This is a spacious, two story, 4 bedroom home with 3 master suites that have their own on-suite bathrooms. Two of these masters have king size beds and TV\'s, the other Master has a queen bed and a TV as well. The 4th bedroom has 2 twin beds and a TV with a Sony play station and games for the kids. There is also a small play area on the balcony .......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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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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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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