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Cottage holiday 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, 217 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!

16–23 Dec

$599 SGD per night

Guest favourite

Cottage in Bradenton

4.94 out of 5 average rating, 302 reviews

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

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 7:30AM. Please respect others. Walk to many great restaurants!

30 Dec – 6 Jan

$257 SGD per night

Guest favourite

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.

18–25 Nov

$263 SGD per night

Guest favourite

Cottage in Sarasota

4.94 out of 5 average rating, 139 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.

6–13 Aug

$175 SGD per night

Guest favourite

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.

11–18 Aug

$165 SGD per night

Guest favourite

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.

1–8 Oct

$316 SGD 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.

24–31 Aug

$256 SGD per night

Guest favourite

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

5–12 Feb

$187 SGD 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!

10–17 Dec

$217 SGD per night

Guest favourite

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!

30 Oct – 6 Nov

$357 SGD per night

Guest favourite

Cottage in Anna Maria

4.98 out of 5 average rating, 208 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.

26 Dec – 2 Jan

$788 SGD per night

Guest favourite

Cottage in Sarasota

4.9 out of 5 average rating, 177 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.

26 Jan – 2 Feb

$191 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Bungalows

Intimate homes, inviting architecture

Popular amenities for cottage rentals in Siesta Key

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Holmes Beach

4.91 out of 5 average rating, 45 reviews

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

28 Sep – 5 Oct

$604 SGD per night

Guest favourite

Cottage in Sarasota

4.96 out of 5 average rating, 23 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

30 Aug – 6 Sep

$462 SGD per night

Guest favourite

Cottage in Bradenton

4.95 out of 5 average rating, 82 reviews

Coastal Cottage w/ Pool & Hot Tub

23–30 Aug

$450 SGD per night

Cottage in Bradenton

5.0 out of 5 average rating, 4 reviews

Cozy Casita Close to Anna Maria Island!

9–16 May

$475 SGD per night

Guest favourite

Cottage in Treasure Island

5.0 out of 5 average rating, 29 reviews

Casa Sunset by Agua Salá

13–20 Jul

$437 SGD per night

Cottage in Bradenton

4.87 out of 5 average rating, 31 reviews

Shangri-Lodge Cabin on 3 Acres

15–22 May

$591 SGD per night

Cottage in Sarasota

4.67 out of 5 average rating, 3 reviews

Cozy Cottage at Sun Outdoors Sarasota

20–27 Nov

$192 SGD per night

Cottage in Port Charlotte

5.0 out of 5 average rating, 3 reviews

Cute Port Charlotte Home w/ Resort Amenities!

1–8 Feb

$376 SGD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 135 reviews

The Pelicans Roost / Gulfport

9–16 Aug

$162 SGD per night

Guest favourite

Cottage in Englewood

4.96 out of 5 average rating, 139 reviews

Family-Friendly Beach Cottage Manasota Key

11–18 Nov

$316 SGD per night

Guest favourite

Cottage in Gulfport

4.99 out of 5 average rating, 257 reviews

Gulfport Art District - One Block From Beach!

22–29 Oct

$245 SGD 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

16–23 Nov

$609 SGD per night

Guest favourite

Cottage in Bradenton Beach

4.86 out of 5 average rating, 123 reviews

AMI Beach Shack

26 Nov – 3 Dec

$596 SGD per night

Cottage in Sarasota

4.81 out of 5 average rating, 154 reviews

Dog friendly Cottage

11–18 Oct

$232 SGD per night

Guest favourite

Cottage in Siesta Key

4.83 out of 5 average rating, 41 reviews

Awesome spot on Siesta Key - Walk to Everything!

15–22 Jul

$271 SGD per night

Guest favourite

Cottage in Sarasota

5.0 out of 5 average rating, 23 reviews

Cozy Cottage near Siesta Key Beach

18–25 Sep

$205 SGD per night

Private cottage rentals

Guest favourite

Cottage in Treasure Island

4.97 out of 5 average rating, 151 reviews

Peacock Beach Cabana beach in 100 steps

15–22 Dec

$267 SGD per night

Guest favourite

Cottage in Sarasota

4.83 out of 5 average rating, 108 reviews

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

10–17 Dec

$324 SGD per night

Guest favourite

Cottage in Bradenton Beach

4.91 out of 5 average rating, 129 reviews

Historic Beach Cottage with private garden

1–8 Oct

$429 SGD per night

Guest favourite

Cottage in Sarasota

4.87 out of 5 average rating, 131 reviews

Charming Lido Cottage

31 Oct – 7 Nov

$415 SGD per night

Guest favourite

Cottage in Gulfport

4.95 out of 5 average rating, 237 reviews

Gulfport Cottage STEPS to Beach & Restaurants

1–8 Aug

$256 SGD per night

Guest favourite

Cottage in Bradenton Beach

4.91 out of 5 average rating, 183 reviews

Ebb Tide @ Tides Inn

11–18 Aug

$389 SGD per night

Guest favourite

Cottage in Bradenton Beach

4.9 out of 5 average rating, 170 reviews

Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach

3–10 Feb

$396 SGD per night

Guest favourite

Cottage in Siesta Key

4.94 out of 5 average rating, 67 reviews

Surf Shack- Walk to Village/Boat Dock Included

7–14 Apr

$239 SGD 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
$202 SGD before taxes and fees

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