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Stay steps from the sand in a Sarasota Vacation Cottages for Rent designed for convenience, coastal style, and those perfect Gulf Coast sunsets — ideal for couples, families, and anyone who wants a seamless beach getaway.
Vacation Rentals by Owner in Sarasota, Florida.
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To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website. All bookings are securely completed on our partner websites.
1-bedroom cottage just 10 minutes from Siesta Key Beach
Charming completely independent one bedroomed mother-in-law suite which is attached to the back of the main house. There is a private entrance with private fenced in back yard/patio with lanai and hot tub. The bedroom includes a king size bed and walk in closet with large ensuite bathroom. The living room has a wood burning fireplace and a smart T.V with Roku, Kitchen seats 4 people. There is a refrigerator, dishwasher, microwave, crockpot, coffee maker, electric stove top and outdoor grill. Sp.......
Just a three minute walk from the white sand of the world renowned Siesta Beach
Nestled on the serene and inviting Crescent Street, a true wood picket fence is the classic cottage signature which perfectly frames the tropical landscaping and delightful curb appeal.
Modern comforts of the 1,465 square foot cottage include a new kitchen with Granite counter tops, tile back splash, new stainless appliances, new front loader washer and dryer.
The floor plan gives an abundance of natural light, its a bright and sunny cottage near the sea's edge.
The graciou.......
10.0 Star Rating
3 Bedrooms
- Sleeps 6
Sarasota Vacation Rental
Pet Friendly 
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Cottage style 2 bedroom 1 bath condo in Siesta Key is just a 2-3 min walk to the Pool, Beach, Restaurants and shops.
(Also see our other listings 1012678 & 1569737)
Do you prefer a single-story, ground floor cottage over a high-rise? A garden patio over a balcony? This might be your best Siesta Key vacation yet!
Our Cottage comes complete with comfortable, quality furniture, and top quality bedding and linens.
Fully equipped, offering everything you need for a fun and.......
Storybook Cottage in a Dream Location - Private Pool, Near Siesta & More
Rent my one-bedroom, one-bath completely furnished historic guest cottage and feel instantly at home. Enjoy waking up to the sounds of tropical birds. Read the Sunday paper over a cup of coffee or tea in the sunny private courtyard. Take a morning walk down to the water and watch the fish jump.
The 750 square foot cottage is perfect for the single traveler or snowbird couple. There are no steep stairs to climb or elevators to take. Park your car(s) in the private guest drive.
Th.......
10.0 Star Rating
1 Bedrooms
- Sleeps 2
Sarasota Vacation Rental
Pet Friendly
Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
Our home is a beautifully remodeled and charming two bed, two bath situated in the perfect area. We just added a brand new heated pool/spa covered with a lanai to keep out the bugs.
The home is on a quiet, tree lined street. A quick 10 minute drive to Siesta Key Beach (consistently rated #1 beach in the US) and a 10 minute drive to downtown Sarasota. Great restaurants and shops are all within walking distance. Everything that you need for a comfortable, convenient stay is waiting here for you.......
Bright Sarasota Bungalow - 5 Mi to Siesta Beach!
Looking for a tropical escape? This cozy cottage is perfect for you! A short drive or bike ride will be all that separates you from Siesta Key and some of the best beaches in West Florida. You'll be within walking distance of fantastic local restaurants and only 3 miles south of downtown Sarasota where you can find excellent museums and parks. With 2 bedrooms and 2 baths, this lovely craftsman-constructed vacation rental will meet all your needs for a sunny weekend stay with friends or family!
?Book Me Baby! Pool, Pet-Friendly Paradise Near Downtown Sarasota?
Pinkie Flamingo Welcomes You To Hazel's Hideaway!
Three month (90 Day) Min For Season. Just nine blocks from Sarasota's bustling Main Street, cottage guests can enjoy a private and serene poolside setting and a 30-foot lap pool in an historic neighborhood. This cute one-bedroom bungalow has a separate king bedroom, full bath, kitchenette and living room. Less than two blocks away is Gillespie Park, with tennis courts, basketball courts, dog park, pond and gazebo. This charming pet-friendl.......
SRQ Beach Cottage
Stay in, what locals consider to be one of the most sought after areas of Sarasota -West Of The Trail. Loved for its absolutely perfect location- close to world famous Siesta Key, downtown, restaurants, shopping and many great parks. It is an area where time has stood still-neighbors warmly greet you and kids still play outside.
This well manicured cottage has been lovingly remodeled with a touch of modern fixtures and upgrades while still maintaining all of the home's charm. Stroll down past.......
10.0 Star Rating
3 Bedrooms
- Sleeps 5
Sarasota Vacation Rental
Pet Friendly
Location! walk to bay, New College, Ringling Museum, downtown and the beaches
Light filled, walk to the bay and Ringling Museum. This one-bedroom, 750-sf Cottage is perfect for a single traveler or a couple. Located in an upscale, quiet neighborhood only a five-minute walk to the gorgeous bay - perfect for sunsets! Yet, it is close to all the action. Walking distance (just a few blocks) Ringling Museum, and the Asolo Theatre.
The Cottage has one bedroom, one bathroom, a full kitchen, living room, and a screened lanai. The bright and spacious bedroom has a king-size.......
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A sunny Siesta Key adventure is made even better for those who book a stay in beautiful Beach Road. This welcoming 2-bed, 2-bath home away from home offers up enough space to accommodate 6 guests at a time making it an ideal property for a group of friends or a family getaway. Beach Road enjoys a prime location directly across the street from Siesta Key Beach and is only mere blocks from exciting stops like Siesta Key Village. Whether you're looking to cozy up or head out and enjoy the best of l.......
NEW...Lido Key Cottage
Vacation rental: 'Olde Florida' style 2 bedroom, 1 bath cottage one block from Lido Beach! Nestled in the back of Pelican Gardens, this tropical Villa is a short stroll to Ted Sperling Park and St. Armands Circle. Just bring your suitcase and sunglasses. Sunscreen provided! Kitchen is perfectly set up for cooking or entertaining. Between dining area or breakfast bar there's plenty of room! Master bedroom features King accommodations and opens to side deck. Guest room provides both a full bed and.......
Sarasota Getaway Near Siesta Key, Screened Lanai + Garage, Pet Friendly
Welcome to Sun-Kissed Cottage, your comfortable Sarasota home base just minutes from the world-famous beaches of Siesta Key!
Located in the quiet Gulf Gate Estates neighborhood, this inviting 2-bedroom home puts you close to the best of Sarasota while giving you a peaceful place to relax at the end of the day. Spend your mornings at the beach, explore nearby Gulf Gate’s restaurants and local shops, bike the Legacy Trail, or simply slow down and enjoy the screened lanai and large backyar.......
10.0 Star Rating
2 Bedrooms
- Sleeps 6
Sarasota Vacation Rental
Pet Friendly
Siesta Keys Neighbor 5min to Beach - Entire Suite Apartment
Summary:
Indulge in the ultimate Siesta Key experience at our coastal-style private (not shared) suite in Sarasota, just minutes from the breathtaking beach. Whether you drive 5 minutes to the country's voted best beach or bike to the sandy shores, you can’t go wrong. Discover vibrant restaurants, groceries, shopping, and laundromat within 5-10 minutes from the doorstep. Our suite features a fully stocked kitchen, 1BR/ 1BA, a private patio with outdoor shower, and free parking on a quie.......
Unique 2-BDRM in Sun Outdoors Sarasota Resort - Includes Golf Cart - Sleeps 6!
This private 2-bdrm cottage is located in the HUGE, highly sought-after Sun Outdoors Sarasota Resort with amenities and activities galore! Our spacious lanai with a unique bonus kitchenette is great for families and entertaining. Complimentary use of private golf cart is included at no extra charge!!
Guests will have full access to the large heated outdoor pool complex with bar and grill, two hot tubs, water slide and splash pad -- plus plenty of pool-side seating available for swimmers a.......
10.0 Star Rating
2 Bedrooms
- Sleeps 6
Sarasota Vacation Rental
Pet Friendly
Bayview Cottage - Cozy Cottage near Siesta Key by The Bay & Key Collection
Nestled in a picturesque Sarasota neighborhood, this enchanting cottage brims with rich history and one-of-a-kind character. Unwind in the private jacuzzi hot tub, tucked into a lush garden dotted with prolific fruit trees. Thoughtful eco-friendly touches elevate every stay — from organic cotton sheets and vegan mattresses to warm, reclaimed-wood furnishings — for a retreat that feels as good as it looks.
Siesta Key Beach, Short drive to downtown Sarsota, Sarasota's cultural scene enc.......
10.0 Star Rating
2 Bedrooms
- Sleeps 4
Sarasota Vacation Rental
Pet Friendly
Cozy 2Bd+2 Ba beach cottage; scrnd FL rm, 5min thru dune to bch; VR22-00059
Perfect, private retreat! Time slips into Beach time, where nature guides your days and evenings. Fully renovated post 2024 hurricanes. Ready to welcome you!
Sparkling Florida Beach Cottage combines top amenities with traditional charm. Located one driveway to the secluded beach path on the quiet north end of Lido Key. Relish your quiet beach, collect shells and sand dollars, watch pelicans and sea hawks dive for their meals...Away from the high rises, condos and cars - slip into wave-ti.......
Roomy Cottage: 4bd3 ba; 2,000 sq ft; 5min thru dune 2 bch; priv pool VR22-00058
One level FL Beach Cottage, 3rd house from Beach Path on N end of Lido Beach. This is a rare find in a nice quiet neighborhood, steps away from spectacular sunsets, fine dining and shopping! Our guests rave it is the perfect cottage to enjoy multi-generation families and friends - the cottage's layout truly caters to quiet bedrooms and plenty of gathering spaces.
Ideally located, 3rd House from the beach path and 3 blocks from the highly sought after St Armands Circle - the location canno.......
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
This is the perfect spot for those looking for a peaceful retreat with all the excitement just a stone's throw away! You'll be thrilled to know that the stunning Siesta Beach is only 8 minutes away and the vibrant downtown is just 6 minutes away. Get ready for an unforgettable adventure!.......
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
Lido Beach is one of the most beautiful beaches, not only in Florida, but in the United States. The beach has soft, silky white sand! The world famous sunsets off the shores of Lido Beach draw not only our visitors but local residents as well ... all there to soak in one of nature's most spectacular performances! The view is so surreal that it’s not uncommon to see people clap their hands in the joy they receive from this experience. All of this is just a short stroll from the cottage which .......
Sarasota, Fl. Wild Orchid Creek
Come enjoy old Florida living at this completely renovated cottage style home on nearly 7 acres. Relax and unwind in this 1000 square foot home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of our oak trees bloom in early summer.
A BIT MORE AB.......
10.0 Star Rating
1 Bedrooms
- Sleeps 4
Sarasota Vacation Rental
Pet Friendly
Studio House in Prime Location - close to Siesta Key Beach and Downtown
Completely renovated studio - a coach house on a lot with another house. New kitchen, new bathroom, new floor, new furniture, freshly painted. Fantastic location in a quiet and beautiful Granada neighborhood, just a mile to Siesta Key, short distance to downtown, Southside Village, many restaurants and Sarasota Memorial Hospital. Sleeps 4: 1 queen bed + 1 sofa sleeper........
1 Bedrooms
- Sleeps 4
Sarasota Vacation Rental
Cozy 2 Bed, 1 Bath cottage close to Downtown Sarasota and the Beaches
This is a 2 bedroomed, one bath house, centrally located near downtown Sarasota, pet friendly within walking distance to a great dog and family park that also has yoga, sports, and an Olympic size heated pool for only $2 a day entrance fee. Siesta Key beach and Lido Beach are both a 15 minute drive away or you can take the Siesta Key trolley bus at the top of the road. You won't have to drive far to enjoy all the amenities Sarasota has to offer, 5 minute drive to fabulous restaurants, supermarke.......
The Cottage Next Door Best Downtown location in Sarasota
Recently restored 1925 cottage nestled in the heart of Sarasota's newest and most desirable downtown neighborhood and just steps away from Sarasota Bay.
It's simply the perfect place for a couple's getaway, honeymoon week, weekend away with a friend (or two or three) or visiting friends and family in SRQ. The Cottage Next Door is available 3-night minimum, weekly or monthly.
Immaculately renovated and tastefully furnished to accentuate all the charm & energy of this unique vintag.......
Beach-Themed Cozy Cottage Close to Downtown, Beaches, Pinecraft & Legacy Trail!
Charming Sarasota Retreat | Near Beaches, Trails & Pinecraft
Welcome to your peaceful Sarasota getaway! Located in a quiet neighborhood, this comfortable and well-appointed home offers everything you need for a relaxing stay.
Step out onto the backyard patio to enjoy your morning coffee or evening wine, complete with outdoor seating and a spacious yard perfect for soaking up the Florida sun.
Inside, you'll find cozy furnishings, a bathtub/shower combo, and a fully equipped.......
LJ's Cottages 4 BALCONY BEACH AND POOL
Summary:
BALCONY VIEWS - 2 bedroom, 2 bathroom second floor bungalow style unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Our massive living room and dining area are perfect for relaxing after a long day at the beach. The properties amenities boast private balconies, tiki hut, shared pool, hot tub, grill, and parking........
LJ's Cottages 1 - POOL BEACH SUNSET
Summary:
STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, shared pool, hot tub, grill, and parking.
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LJ's Cottages 3 - BALCONY BEACH POOL SAND SUNSETS
Summary:
STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our second floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dining room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, shared pool, hot tub, grill, and parking.<.......
LJ's Cottage 2 - POOL BEACH SUNSETS BALCONY
Summary:
STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.
.......
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard
Welcome to the Coconut Cottage! Adorable historic coastal bungalow 10 minutes from Siesta Key and beaches! (4.5 Miles away from South Siesta Key beach access). (North Jetty beach (Venice) is approx 9 miles in other direction). Interior of home has been recently updated. Quaint and cozy feel with coastal charm. Home is approx. 700 sq. feet with 2 bedrooms and 1 bathroom. Open kitchen area. Smart TV. . Free WIFI. Large spacious partially fenced backyard with tropical vibe and many trees.......
Coastal Gem!
Escape to paradise in this charming cottage nestled just 250 steps from the white sands of the Gulf. Conveniently located 1\/2 block to Lido Beach and close to the fabulous restaurants and shopping of St. Armands Circle. Whether you’re sipping your morning coffee in the private fenced yard, grilling fresh catch on the BBQ, or relaxing in the fully furnished comfort inside, you’ll find everything you need for a relaxing Florida getaway. Private location features 2 bedrooms and 1 bath. King s.......
The Urban Cottage Downtown Sarasota
It’s shabby chic meets high tech and it’s all in the details! Elegant, light and airy and just darn adorable best describes The Urban Cottage. Guests rave about The Urban Cottage and have given over 25 5 Star ratings. Come and experience the luxury of a perfect couples get away! Monthly discounts are available.
The Urban Cottage at The Bryant House is a newly restored 950 square foot .......
Near Siesta Key with Private Pickleball Court and Heated Saltwater Pool with Spa
**PRIVATE PICKLEBALL COURT** *HEATED SALTWATER POOL + SPA* Your family will feel at home in this newly remodeled single family home, just minutes to the #1 beach in the USA and downtown Sarasota! With a large backyard featuring a fire pit and swing for the kids and a pickleball court, comfortable beds, a large open kitchen stocked with essentials for preparing meals, you may never want to leave! The location is convenient to several grocery stores, many restaurants and shopping an.......
Charming 1/1 condo at Palm Bay Club in Sarasota, with stunning east views.
This one bedroom one bathroom condo is located on the ninth floor of our Grande Tower Building. Because it is located in the Tower, it is an easy stroll to the beach. There you can to enjoy our white quartz sand, and the Gulf's warm waters. The unit's living room and dining room areas are combined to extend your entertaining space and has a 43" flat screen TV with DTV service. The master bedroom has two queen sized beds with a 32" flat screen TV. The bathroom has a tub/ shower combination. This .......
Lido Key House- Ultimate Beach Escape, Steps from the beach & St. Armand's
NEWLY RENOVATED!!! Ready for the ultimate Lido Beach getaway? This charming unit offers the perfect launchpad for your Florida adventures, delivering incredible access to all the Lido Key magic! Step inside to a comfortable haven designed for relaxed beach living. You'll find a king-size bed in the primary bedroom for peaceful nights, and a queen-size bed in the second bedroom, providing ample space for your group. The living room features a smart TV and a cozy seating area with a sleeper sofa, .......
Large Renovated Studio-Steps to beach and walk to St. Armand's
NEWLY RENOVATED!!! Ready to swap your shoes for flip-flops? Discover Mermaid For A Day, a vibrant studio unit on Lido Key, offering the ultimate beachside escape! This is where comfort meets unparalleled convenience, putting you right in the heart of Lido's magic. Inside, you'll find everything you need for a carefree vacation: a cozy king-size bed for restful nights, a refreshing walk-in shower, and a full kitchen ready for your beach-day snacks or morning coffee. The living area is designed fo.......
Close to Nathan Benderson-Owl's Nest Eco-Cottage
Charming Key West-style Cottage- just minutes from beaches and all Sarasota has to offer! Perfect for nature lovers and eco-friendly travelers.
The space
The Owl's Nest Eco Cottage is part of a larger 2 acre property shaded by mature oak trees and wild, lush landscaping. It is conveniently located just minutes from Downtown and several amazing beaches. It is just 5 mins from Nathan Benderson Rowing Park and convenient for rowing events.
The property is newly redone and redecorated. .......