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Siesta Key Cottage Rentals
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Stay steps from the sand in a Siesta Key Beachfront Cottage designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless beach getaway.
Vacation Rentals by Owner in Florida.
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Search for Vacation Rental options here, then Book Securely on our partner site.
Key West style beach cottage JUST STEPS from #1 SIESTA KEY BEACH!
**PLEASE do NOT request to book before contacting hosts. USE "Contact Host button" (blue letters under book now button - scroll down) 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 from Siesta Village. CUTE one story "fishing cottage" takes you back to "the old Key" with a private Key West style courtyard with swing and .......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Siesta Key Vacation Rental
Pets Allowed 
Cabana Cottage Across street from Beach and Heated Pool
The Cabana is small but mighty! A fully equipped kitchen complete with granite countertops, and a breakfast bar, with all of the comforts of home.The master bedroom has a King size Serta ICOMFORT Memory Foam Gel bed with a flat screen TV, and an attached European Rain shower bath. The second bedroom is two, twin Serta ICOMFORT Memory Foam Gel beds with a flat screen TV. The second tub/shower bathroom is off the kitchen area. Living room and dining areas are combined, equipped with 65 flat screen.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Siesta Key Vacation Rental
Pets Allowed
Lookout Cottage Across street from Beach and Heated Pool
This upstairs suite has a tiny glimpse of the Gulf of Mexico between the two homes across the street from the roomy balcony. This bright, airy unit makes you feel at home.The tub/shower bath is directly off the fully equipped kitchen. The bedroom hosts a King Serta ICOMFORT Memory Foam Gel bed, also a flat screen TV in the master bedroom. The living-dining rooms are combined and have comfortable overstuffed denim slipcovered couch and a Stressless chair to enjoy, along with a 55 flat-screen TV a.......
Nook Cottage Across street from beach and Heated Pool
This is a ground floor, one bedroom, one bath unit with King-size Serta ICOMFORT CF 3000 Memory Foam Gel Series bed in the master and full bath off of the bedroom, ensuite. Large walk-in tile shower with glass enclosure.The Nook features a fully equipped kitchen with granite counter tops and cozy dining area and beach chic laminate wood flooring throughout. This unit is naturally bright and spacious, with white-washed tongue and groove accent walls. Enjoy a flat screen, 55 inch TV in Living, DVD.......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Siesta Key Vacation Rental
Pets Allowed
Haven cottage Across street from beach and Heated Pool
This suite is ground level, just a few steps from pool-side. This roomy and bright unit with all tile floors on the diagonal, has a combined living and dining area, with an open-air balcony off the living room with a 6-foot sliding glass door.The leather couch adds to the comfort while watching the 65" flat screen TV with Blu-ray player. A fully equipped kitchen with granite counter tops and breakfast bar, have all the comforts of home. The master bedroom includes a Serta ICOMFORT Memory Foam Ge.......
Nest Cottage Across street from beach and Heated Pool
Upstairs with its own stairway off the pool area, this suite feels like a tree house. There are about 20 stairs, with a nice landing halfway, to reach your destination. This roomy unit has a combined living and dining area, with an open-air balcony off the living room with a 6-foot sliding glass door.The leather reclining couch adds to the comfort while watching the 65 flat screen TV with DVD player. A fully equipped kitchen has all the comforts of home. The master bedroom includes a King size S.......
Cozy Cottage with Hot Tub
Take it easy at this unique and tranquil getaway. Equipped with all the essentials for a beach vacation all you will need is sunscreen and bathing suits! You are just a few minute walk to the Village with night life and great restaurants. If you are looking for more space there is also a 3 bedroom 3 bath house that neighbors this Cottage that can be rented by itself. Or if you need both we can arrange this as well just inquire and we will see if we have both open!.......
Location. 3 bedroom cottage block from beach and two blocks from Siesta Village
Location, location, location. Our charming 3-bedroom 2 bath Florida beach cottage, which is over 1000 feet and sleeps 6, which we call the “Manatee 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 States (you will be a 5 minute walk from access 7). Enjoy the amazing sunsets each night of your stay without the hassles of traffic, parking and crowds.
You will also be 2 blocks from Siesta .......
9.6 Star Review
3 Bedrooms
- Sleeps 6
Siesta Key Vacation Rental
Pets Allowed
Location 1 Bdrm Cottage 1 Block from Beach and 2 Blocks from Siesta Village
Location, location, location. Our charming 1 bedroom, 1 bath Florida beach cottage which is over 800 sq. feet and sleeps 2 which we call the "Dolphin Cottage" is across the street from the soft white sand of the world famous Siesta Key Beach which is consistently rated the best beach in the United States (you will be a 5 minutes walk from Access 7). Enjoy the amazing sunsets each night of your stay without the hassles of traffic, parking, and crowds.
You will also be 2 blocks from Siest.......
9.8 Star Review
1 Bedrooms
- Sleeps 2
Siesta Key Vacation Rental
Pets Allowed
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Summary:
*Siesta Key elevated villa at Solitude Suites on Siesta Key.
*Your own detached private villa, located in a small resort.
*Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Huts.
* Just a 10-12 min walk to award winning beach.
*1 Bedroom w/King bed.
*1 full bathroom w/shower.
*Large kitchen, open living room, fully furnished inc towels & linens.
*Private lanai w/ table & chairs.
*Beautiful shared pool w/ sun .......
Exquisite Small Cottage Minutes to Siesta Key
Very upscale, full kitchen with granite counter, double bed, indoor + outdoor dining for four, Weber grill, wood deck, hammock, porch, Adirondack chairs. Drive in gated 1/4 acre lot, six foot privacy fence. Smart TV, Bluetooth sound bar. Internet. GE Advantium Oven, Induction Cooking surface, Air Fryer, very high end knives ,cookware, etc. Wine and champagne flutes. Keurig w/pods. Hotel quality linens and towels. Beach chairs, beach towels and cooler. Utter privacy in a very cool "Tiny House"
Across The Street From #1 Beach
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 look out the front window and see the Beach Access #7 sign.
If your looking for some lunch after a day at the beach walk out the front door of The Siesta Key Beach Cottage and head right up to the Village. There you will find any type of food yo.......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Siesta Key Vacation Rental
Pets Allowed
Luxury Beach Cottage on Siesta Key: Perfect Getaway, private pool.
Newly renovated Charming Beach Cottage with tongue and groove wood cathedral ceilings, tile bath, new appliances including, dishwasher, refrigerator and freezer, microwave, air conditioner, and washer and dryer located on two beautifully landscaped acres on the Beach. Big glass sliding doors to enjoy view of gardens and Koi pond. The cottage is located on a beach front property, the tide only allows access to the sand when it is low. This is the only rental on the property, but it does share the.......
9.4 Star Review
1 Bedrooms
- Sleeps 2
Siesta Key Vacation Rental
Pets Allowed
? Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
🌴 Palm Shade Cottage | 0.1 Miles to Siesta Key Beach + Shared Heated Pool
đź’– Why You'll Love This Home
Step into your private Siesta Key cottage, a cozy retreat with lush landscaping and a screened-in heated pool shared with Coconut House. This 1-bedroom home offers a charming escape for couples or a small family, just 0.1 miles from the world-famous white sands of Siesta Key Beach.
👨‍👩‍👧 Perfect For
Couples or small families seeking an intimate space with p.......
5 Min walk to Beach & Village, Private Pool,On the Canal
Sophie's has been completely remodeled. Welcome to Sophie's Cottage, a peaceful waterfront retreat. The cottages is a vacation place for families or a romantic getaway for couples. There are 2 private bedrooms and 2 bathrooms: 1 king bed, 1 queen bed, 1 queen bed and queen sleeper sofa in pool side room. This room is not closed off see pictuers. 1 full size sofa bed in living room,they have gel foam mattresses. The dining room, living room and den all make a cohesive space for entertainment or .......
9.8 Star Review
4 Bedrooms
- Sleeps 8
Siesta Key Vacation Rental
Pets Allowed
Charming Cottage Near Siesta Key Village!
Step into tranquility at this charming 1-bedroom cottage, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Complete with a private kitchen, living room, and an onsite shared pool and hot tub, this cottage is perfect for winding down after a day in the popular Siesta Key Village or soaking in that Florida sun!
The Space:
Bedroom: King
Living room: Queen Sofa Bed
Cozy Cottage Near Siesta Key Village!
Step into tranquility at this charming 1-bedroom cottage, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Complete with a private kitchen, living room, and an onsite shared pool and hot tub, this cottage is perfect for winding down after a day in the popular Siesta Key Village or soaking in that Florida sun!
The Space:
Bedroom: King
Living room: Queen Sofa Bed
Cottage Across The Street From #1 Beach
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.
If you're looking for some lunch after a day at the beach, go out the front door of The Siesta Key Beach Cottage and stroll around the corner up to the Village. There you will find any type of food you can imagine. If the sun has made you thirsty there a.......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Siesta Key Vacation Rental
Pets Allowed
Blue Dolphin Cottage steps from the beach
Enjoy this Key West style cottage equipped to sleep 3 guests. Boasting 2 bedrooms and 1 bath, the master bedroom has a king bed and the second room has a twin. Great for small families travelling and looking to save on some meal cooked in with the kitchenette which can handle most home cooked meals. Also relax on your private screened in porch after a day tanning in the sun as the beach is 100 ft away! With roughly 400 sqft of living space you will surely be able to relax and immerse yourself in.......
2 Bedrooms
- Sleeps 3
Siesta Key Vacation Rental
Tropical Beach Cottage-Steps to the Beach-Short Walk to Siesta Key Village
Welcome to Beach Point Cottages on Siesta Key! We are 8 unique cottages, ranging from studios to 2-bedrooms, on a property filled with tropical plants and quirky art. Discover vibrant Cottage 1, a two-bedroom cottage with everything you need. Excellent location-just across the street from the beach and a very short walk to Siesta Key Village. Guests will enjoy two en-suite bedrooms, each with King sized beds. Bringing a couple of kiddos? The living room features a queen-sized sofa sleeper, to co.......
2 Bedrooms
- Sleeps 6
Siesta Key Vacation Rental
Pets Allowed
All-New, Walk to Beach & Village, Private and Cozy
Welcome to Siesta Shores! Located directly across the street from Siesta Key Beach Access #7 and just two blocks to the Village! This adorable beach cottage is ALL-NEW from top to bottom: New furniture, New kitchen, New bathroom, New everything! Living room has a full size sleeper sofa, Large Smart TV and strong Wifi. Oversized-King bed and cute kitchen. Onsite laundry room and extra guest parking. The perfect location to see and experience the BEST of Siesta Key! You will love it here!
10.0 Star Review
2 Bedrooms
- Sleeps 4
Siesta Key Vacation Rental
Pets Allowed
Siesta Key Village Cottage , 3 blocks to beach, Large private heated pool
Updated 3 bedroom cottage ideally located in the village. Walk to many restaurants, nightclubs/bars with live entertainment. 3 blocks to beach! NO STEPS to climb! Large backyard with private heated salt pool with sundeck, patio, lanai, gazebo, fire pit, gas BBQ grill, 2 bicycles. outdoor shower, pet friendly, bag toss, mini golf, beach wagon, beach chairs, fenced yard, covered carport, internet, 3 high def TVs, washer and dryer Close enough for all the excitement of the village, yet far enough.......
9.8 Star Review
3 Bedrooms
- Sleeps 6
Siesta Key Vacation Rental
Pets Allowed