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Cottage holiday rentals in Siesta Key

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Top-rated cottage rentals in Siesta Key

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Cottage in Siesta Key

4.88 out of 5 average rating, 218 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!

Guest favourite

Cottage in Bradenton Beach

4.97 out of 5 average rating, 143 reviews

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 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.

Guest favourite

Cottage in Myakka City

4.99 out of 5 average rating, 115 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.

Guest favourite

Cottage in Sarasota

4.94 out of 5 average rating, 142 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.

Guest favourite

Cottage in Bradenton

4.96 out of 5 average rating, 101 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

Guest favourite

Cottage in Nokomis

4.98 out of 5 average rating, 124 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.

Cottage in Siesta Key

4.84 out of 5 average rating, 134 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.

Guest favourite

Cottage in Bradenton

4.94 out of 5 average rating, 154 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

Cottage in Sarasota

4.83 out of 5 average rating, 151 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!

Guest favourite

Cottage in Siesta Key

4.89 out of 5 average rating, 145 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!

Guest favourite

Cottage in Anna Maria

4.98 out of 5 average rating, 209 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.

Guest favourite

Cottage in Sarasota

4.9 out of 5 average rating, 178 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.

Holiday rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes, inviting architecture

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for cottage rentals in Siesta Key

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Siesta Key

4.91 out of 5 average rating, 47 reviews

Cozy Cottage 1 block from Beach

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 23 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

Cottage in Venice

4.64 out of 5 average rating, 25 reviews

BarefootBeachBungalow@Ramblers Rest Resort!

Guest favourite

Cottage in Bradenton

4.95 out of 5 average rating, 82 reviews

Coastal Home w/ Pool, Hot Tub 15 minutes to Beach

Cottage in Bradenton

5.0 out of 5 average rating, 4 reviews

Cozy Casita Close to Anna Maria Island!

Guest favourite

Cottage in Treasure Island

5.0 out of 5 average rating, 30 reviews

Casa Sunset by Agua Salá

Cottage in Bradenton

4.87 out of 5 average rating, 31 reviews

Shangri-Lodge Cabin on 3 Acres

Cottage in Port Charlotte

5.0 out of 5 average rating, 3 reviews

Cute Port Charlotte Home w/ Resort Amenities!

Pet-friendly cottage rentals

Guest favourite

Cottage in Gulfport

4.99 out of 5 average rating, 259 reviews

Gulfport Art District - One Block From Beach!

Guest favourite

Cottage in Treasure Island

4.93 out of 5 average rating, 102 reviews

Treasure Island Beach Cottage

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 136 reviews

The Pelicans Roost / Gulfport

Guest favourite

Cottage in Englewood

4.96 out of 5 average rating, 141 reviews

Family-Friendly Beach Cottage Manasota Key

Guest favourite

Cottage in St. Petersburg

4.96 out of 5 average rating, 127 reviews

Homey Cottage Close To It All

Guest favourite

Cottage in Sarasota

5.0 out of 5 average rating, 23 reviews

Cozy Cottage near Siesta Key Beach

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 69 reviews

Luxury large cottage-studio/wth kitchen & bathroom

Cottage in Siesta Key

4.88 out of 5 average rating, 86 reviews

Walk to Beach & 5 blocks to Village

Private cottage rentals

Guest favourite

Cottage in Treasure Island

5.0 out of 5 average rating, 179 reviews

Island Time Stay: Sunset

Guest favourite

Cottage in Bradenton

4.93 out of 5 average rating, 305 reviews

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

Guest favourite

Cottage in Sarasota

4.83 out of 5 average rating, 108 reviews

Walk to Beach & St. Armands/Private cottage &grill

Guest favourite

Cottage in Treasure Island

4.97 out of 5 average rating, 152 reviews

Peacock Beach Cabana beach in 100 steps

Guest favourite

Cottage in St. Petersburg

4.92 out of 5 average rating, 125 reviews

Private Guesthouse- walk to downtown St. Pete!

Guest favourite

Cottage in Bradenton Beach

4.92 out of 5 average rating, 130 reviews

Historic Beach Cottage with private garden

Guest favourite

Cottage in Gulfport

4.95 out of 5 average rating, 241 reviews

Gulfport Cottage STEPS to Beach & Restaurants

Guest favourite

Cottage in Sarasota

4.86 out of 5 average rating, 132 reviews

Charming Lido Cottage

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
2T reviews
Nightly prices starting at
₹12,497 before taxes and fees

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