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Cottage vacation rentals in Siesta Key

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Top-rated cottage rentals in Siesta Key

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Cottage in Siesta Key

4.88 out of 5 average rating, 215 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ FREE pool, kayaks, stand up paddle boards & Tiki Hut. * 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 screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Oct 30 – Nov 6

G$90,960 GYD per night

Cottage in Myakka City

4.99 out of 5 average rating, 113 reviews

NEW! Peaceful Country Cottage near Lakewood Ranch

Enjoy the peace and solitude of the country at this fully renovated cottage. "Country Oaks" Cottage located on seven acres surrounded by nothing but woods and wildlife. We are located approximately 15 miles east of I-75 where you can enjoy privacy away from the bustling city but close enough to enjoy shopping and restaurant options in nearby Lakewood Ranch. Enjoy a trip to historic Arcadia for antique shopping or adventure out to Myakka State Park or TreeUmph! or even local beaches.

Mar 12 – 19

G$39,862 GYD per night

Cottage in Sarasota

4.94 out of 5 average rating, 138 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Fresh Market & Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Nov 18 – 25

G$29,907 GYD per night

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

Aug 11 – 18

G$24,970 GYD per night

Cottage in Bradenton Beach

4.99 out of 5 average rating, 124 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Nov 26 – Dec 3

G$47,992 GYD per night

Cottage in Siesta Key

4.84 out of 5 average rating, 132 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, stocked with everything but your clothes and toothbrush.

Oct 23 – 30

G$48,114 GYD per night

Cottage in Bradenton

4.94 out of 5 average rating, 153 reviews

Cozy Cottage L-Steps to Riverwalk/Close to Beaches

Beautiful cottage style duplex located in Old Downtown West Bradenton in Historic Point Pleasant neighborhood - steps from Riverwalk! Close to beaches!!! Visit RealizeBradenton website for a listing of monthly events , Comfortably sleeps 4 - 1 bedroom with king size bed ,Living area has queen sleeper sofa, Kitchen: well equipped • Guest must disclose if they are bringing a pet and the pet breed • $50 per each 2-7 day stay - per pet

Jul 22 – 29

G$28,334 GYD per night

Cottage in Sarasota

4.83 out of 5 average rating, 150 reviews

Charming Beach Cottage

LOCATION!!! Getaway from the fast paced, high pressure life and slip on some flip flops! Get ready to unwind with the cool sea breeze, sunny adventures on the beach or on the water and explore the meaning of easy island living. Our contemporary designed home is just a few minutes drive from the most picturesque beaches in the nation with LOTS of parking. Feel free to bring your boat:) Restaurants and shopping are plentiful!

Nov 9 – 16

G$32,843 GYD per night

Cottage in Siesta Key

4.89 out of 5 average rating, 143 reviews

Siesta Key Cozy Cottage across from the beach!

Adorable Siesta key cottage one block from the beautiful white sand beach and two blocks from the iconic Siesta Key Village on the north end of the island. Everything is a short walk including all the shops and restaurants of Siesta Village. Very private fenced in yard with barbecue:) Very nice size kitchen with a dining room and a large sunken living room. Both the living room and the bedroom open to the private patio!

Aug 15 – 22

G$54,170 GYD per night

Cottage in Anna Maria

4.98 out of 5 average rating, 207 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Dec 22 – 29

G$119,652 GYD per night

Cottage in Sarasota

4.9 out of 5 average rating, 175 reviews

"Honeybee Hideaway" Cozy Cottage Near SIESTA KEY

Experience the Honeybee cottage, a classic coastal retreat in historic Sarasota, minutes from Siesta key Beach. Enjoy, cozy vibes, modern amenities, fast, Wi-Fi, and shared laundry facilities. Embrace, tranquility and convenience in this charming oasis, combining rich history, with world-class beaches for a memorable getaway.

Dec 4 – 11

G$24,155 GYD per night

Cottage in Sarasota

4.84 out of 5 average rating, 154 reviews

Heated Pool! Beach! Drift Inn Unit B Siesta Key!

Come and enjoy all that Unit B has to offer! This is a cottage style condo, very comfortable and inviting, fully equipped with your beach vacation in mind. The soft white quartz sands of Crescent Beach on Siesta Key are just a 3 minute walk from the cottage door. So is our lovely, saltwater heated pool.

Sep 24 – Oct 1

G$41,264 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Siesta Key cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a pool

Cottage in Sarasota

4.96 out of 5 average rating, 69 reviews

Luxury large cottage-studio/wth kitchen & bathroom

Jun 8 – 15

G$24,273 GYD per night

Cottage in Sarasota

4.91 out of 5 average rating, 33 reviews

La Casita ~ Charming Pool Cottage ~ Tropical Oasis

Oct 21 – 28

G$71,062 GYD per night

Cottage in Sarasota

4.95 out of 5 average rating, 39 reviews

Sarasota Home with pool in resort community

Oct 16 – 23

G$21,573 GYD per night

Cottage in Bradenton

4.96 out of 5 average rating, 96 reviews

Coastal Style 2BR cottage near Anna Maria Island

Aug 20 – 27

G$29,701 GYD per night

Cottage in Nokomis

5.0 out of 5 average rating, 49 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Aug 14 – 21

G$61,172 GYD per night

Cottage in Sarasota

5.0 out of 5 average rating, 32 reviews

Bee Keepers Cottage

Mar 14 – 21

G$94,774 GYD per night

Cottage in Bradenton

4.85 out of 5 average rating, 59 reviews

Cozy! near restaurants, beaches, airport & more

Oct 26 – Nov 2

G$24,258 GYD per night

Cottage in Palmetto

4.96 out of 5 average rating, 70 reviews

Historic 1930s Palmetto Cottage

Nov 12 – 19

G$59,913 GYD per night

Beachfront cottage rentals

Cottage in Bradenton

4.94 out of 5 average rating, 301 reviews

Historic Private King Bed Suite-Near Beach-D’Town.

Apr 1 – 8

G$39,625 GYD per night

Cottage in St Pete Beach

4.98 out of 5 average rating, 158 reviews

Pass-a-Grille Historic Cottage Unit 1

Jul 6 – 13

G$57,896 GYD per night

Cottage in Saint Pete Beach

4.86 out of 5 average rating, 155 reviews

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

Aug 31 – Sep 7

G$83,399 GYD per night

Cottage in Siesta Key

4.94 out of 5 average rating, 67 reviews

Surf Shack- Walk to Village/Boat Dock Included

Nov 3 – 10

G$30,247 GYD per night

Cottage in Sarasota

4.82 out of 5 average rating, 82 reviews

The Best Villa on Siesta Key

Nov 20 – 27

G$47,075 GYD per night

Cottage in Holmes Beach

5.0 out of 5 average rating, 26 reviews

Oleander Villa by Beach Boutique Rentals

Oct 9 – 16

G$48,345 GYD per night

Cottage in Nokomis

4.92 out of 5 average rating, 84 reviews

The "Turtle Cottage" - a charming beachy retreat.

Nov 24 – Dec 1

G$27,606 GYD per night

Cottage in Sarasota

5.0 out of 5 average rating, 18 reviews

Lido Key Beach Bungalow with Private Heated Pool!

Dec 5 – 12

G$102,666 GYD per night

Cottage rentals with a hot tub

Cottage in Siesta Key

4.91 out of 5 average rating, 46 reviews

Cozy Cottage 1 block from Beach

Feb 2 – 9

G$144,954 GYD per night

Cottage in Sarasota

4.82 out of 5 average rating, 34 reviews

Siesta Key Cottages Crescent 1C Beach/Pool/Hot Tub

Nov 18 – 25

G$90,147 GYD per night

Cottage in Sarasota

4.96 out of 5 average rating, 23 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

Nov 10 – 17

G$70,037 GYD per night

Cottage in Holmes Beach

4.91 out of 5 average rating, 45 reviews

Kiwi Cottage *Heated Pool+Spa+ walk to the Beach!

Mar 15 – 22

G$168,116 GYD per night

Cottage in Bradenton

4.95 out of 5 average rating, 82 reviews

Coastal Cottage w/ Pool & Hot Tub

Oct 28 – Nov 4

G$67,320 GYD per night

Cottage in Holmes Beach

Yacht Rock Ranch

Dec 14 – 21

G$158,499 GYD per night

Cottage in Bradenton

4.87 out of 5 average rating, 31 reviews

Shangri-Lodge Cabin on 3 Acres

Jan 27 – Feb 3

G$89,679 GYD per night

Cottage in Sarasota

4.67 out of 5 average rating, 3 reviews

Cozy Cottage at Sun Outdoors Sarasota

Nov 20 – 27

G$29,026 GYD per night

Quick stats about cottage rentals in Siesta Key

Total rentals
20 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
G$31,362 GYD before taxes and fees

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