Sarasota Cottage Rentals

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.......

Cottage in Sarasota
3 Bedroom Sleeps 6
Pet Friendly

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.......

Cottage in Sarasota
2 Bedroom Sleeps 4

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.......

Cottage in Sarasota
1 Bedroom Sleeps 2
Pet Friendly

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.......

Cottage in Sarasota
3 Bedroom Sleeps 6
Pet Friendly

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!

Cottage in Sarasota
2 Bedroom Sleeps 5

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.......

Cottage in Sarasota
1 Bedroom Sleeps 6
Pet Friendly

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.......

Cottage in Sarasota
3 Bedroom Sleeps 5
Pet Friendly

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.......

Cottage in Sarasota
1 Bedroom Sleeps 2

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.......

Cottage in Sarasota
2 Bedroom Sleeps 6

The Sun-Kissed Cottage is conveniently located in Gulf Gate Estates, a short 10-minute drive to the famous white-sand Siesta Key Beach and the lively Siesta Key Village, where you`ll find plenty of dining, shopping and nightlife. The Cottage is just 20 minutes from Downtown Sarasota`s ample cultural activities and events, and you will be just 1 mile from the walkable downtown Gulf Gate area which is loaded with unique shops, multiple delicious international food options, and local hangout spots........

Cottage in Sarasota
2 Bedroom Sleeps 6
Pet Friendly

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.......

Cottage in Sarasota
1 Bedroom Sleeps 2

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.......

Cottage in Sarasota
2 Bedroom Sleeps 6
Pet Friendly

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.......

Cottage in Sarasota
2 Bedroom Sleeps 4
Pet Friendly

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.......

Cottage in Sarasota
2 Bedroom Sleeps 6

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.......

Cottage in Sarasota
4 Bedroom Sleeps 10

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!.......

Cottage in Sarasota
2 Bedroom Sleeps 4
Pet Friendly

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.......

Cottage in Sarasota
1 Bedroom Sleeps 4
Pet Friendly

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........

Cottage in Sarasota
1 Bedroom Sleeps 4

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.......

Cottage in Sarasota
2 Bedroom Sleeps 4

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.......

Cottage in Sarasota
3 Bedroom Sleeps 8

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........

Cottage in Sarasota
2 Bedroom Sleeps 6

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.
<.......

Cottage in Sarasota
2 Bedroom Sleeps 8

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.<.......

Cottage in Sarasota
2 Bedroom Sleeps 8

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.

.......

Cottage in Sarasota
2 Bedroom Sleeps 8

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.......

Cottage in Sarasota
2 Bedroom Sleeps 4
Pet Friendly

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.......

Cottage in Sarasota
2 Bedroom Sleeps 4

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 .......

Cottage in Sarasota
1 Bedroom Sleeps 2

**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.......

Cottage in Sarasota
3 Bedroom Sleeps 8

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 .......

Cottage in Sarasota
1 Bedroom Sleeps 4

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, .......

Cottage in Sarasota
2 Bedroom Sleeps 6
Pet Friendly

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.......

Cottage in Sarasota
1 Bedroom Sleeps 4
Pet Friendly

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. .......

Cottage in Sarasota
1 Bedroom Sleeps 2

Book your Holiday 2026 / Spring 2027 Getaway


*Please note our "Moderate Cancellation Policy" listed only applies to bookings during mid season from May through August . See our Custom Seasonal Cancellation Policy at the bottom of this description and in our Rental Agreement.


Welcome to Lil John Coastal Cottage. Thanks for checking us out! Whether you are staying for a few nights, a week or a month or longer, we look forward to hosting you! Stays of 28 days or longer get a 3.......

Cottage in Sarasota
1 Bedroom Sleeps 4
Pet Friendly

Single-level, private entrance, 900 sf, everything BRAND-NEW inside: Beds, Large Flat Screens, fully-stocked kitchen, washer/dryer, etc. About a 15 minute drive to Siesta Beach or Downtown Sarasota. Walk to restaurants, CineBistro, LA Fitness, Barnes & Nobles, Publix, Trader Joe's & Aldi. No car needed. Walkscore: 70. Extremely safe neighborhood, very quiet too. Nice outside patios in front and back. Walgreens right down the street for last minute needs.

Starter Supplies Provided.......

Cottage in Sarasota
2 Bedroom Sleeps 4
Pet Friendly

Located in Sarasota, this fabulous house offers 1 bedroom with a queen bed. With 1 bathroom equipped with a shower and hair dryer, guests can relax in comfort. An additional living room space with a crib provides extra convenience. Your stay here will be nothing short of phenomenal. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out........

Cottage in Sarasota
1 Bedroom Sleeps 3
Pet Friendly

This memorable cozy park model home is the perfect home base for your trip to Sarasota. Nestled in a tranquil setting, this cozy retreat features 1 bedroom with a queen bed, a large lanai with AC containing a twin over full bunk bed, and a bathroom with a hair dryer. The living room also has brand new queen sofa sleeper. Guests can enjoy the soothing ambiance in the large heated pool, WiFi, AC, and more. You're sure to make fantastic memories with a stay at our place........

Cottage in Sarasota
1 Bedroom Sleeps 6