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Cottage vacation rentals in Casey Key, Florida

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Top-rated cottage rentals in Casey Key, Florida

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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!

Dec 29 – Jan 5

G$90,970 GYD per night

Cottage in Englewood

4.9 out of 5 average rating, 110 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Unit # 2 Beautiful 2 bed 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. This cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Jul 24 – 31

G$29,913 GYD per night

Cottage in Bradenton

4.94 out of 5 average rating, 301 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!

Jul 13 – 20

G$26,743 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.

Jun 6 – 13

G$39,866 GYD per night

Cottage in Bradenton Beach

4.96 out of 5 average rating, 141 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.

Jan 5 – 12

G$65,997 GYD per night

Cottage in Englewood

4.85 out of 5 average rating, 137 reviews

Free Kayaks! Waterfall Pool! Beach! om

In a prime Manasota Key location, our talented interior designer created this beach bungalow gem with 2 bedrooms and sofa sleeper, Smart Tv's & granite kitchen with dining set. Walk only 1 minute until your toes are in Gulf of Mexico at delightfully uncrowded beach! 5 walk to Stump Pass. Longer walk or free shuttle to good restaurants with live music. Unwind in on-site Swim Spa with waterfall & massage therapy jets in common area. Spot dolphins with free Kayaks. Peaceful, quiet

Dec 20 – 27

G$88,640 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.

Jul 19 – 26

G$28,259 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$24,973 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$28,337 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!

Aug 9 – 16

G$32,847 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 28 – Sep 4

G$54,176 GYD per night

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.

Mar 12 – 19

G$118,609 GYD per night

Vacation rentals for every style

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Popular amenities for Casey Key, Florida cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Sarasota

4.74 out of 5 average rating, 108 reviews

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

Nov 30 – Dec 7

G$87,823 GYD per night

Cottage in Siesta Key

4.91 out of 5 average rating, 46 reviews

Cozy Cottage 1 block from Beach

Feb 2 – 9

G$144,971 GYD per night

Cottage in Bradenton

4.95 out of 5 average rating, 82 reviews

Coastal Cottage w/ Pool & Hot Tub

Apr 25 – May 2

G$67,329 GYD per night

Cottage in Sarasota

4.96 out of 5 average rating, 23 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

Oct 1 – 8

G$70,045 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$168,136 GYD per night

Cottage in Holmes Beach

Yacht Rock Ranch

Dec 14 – 21

G$162,677 GYD per night

Cottage in Bokeelia

4.79 out of 5 average rating, 131 reviews

Captains Cottage

May 12 – 19

G$22,320 GYD per night

Cottage in Bradenton

4.87 out of 5 average rating, 31 reviews

Shangri-Lodge Cabin on 3 Acres

May 11 – 18

G$89,690 GYD per night

Pet-friendly cottage rentals

Cottage in Sarasota

4.81 out of 5 average rating, 154 reviews

Dog friendly Cottage

Oct 30 – Nov 6

G$35,128 GYD per night

Cottage in Nokomis

5.0 out of 5 average rating, 49 reviews

New Pool Tropical Waterfront Dock & Optional Boat

Aug 15 – 22

G$61,179 GYD per night

Cottage in Sarasota

4.96 out of 5 average rating, 69 reviews

Luxury large cottage-studio/wth kitchen & bathroom

Jun 8 – 15

G$24,276 GYD per night

Cottage in Sarasota

5.0 out of 5 average rating, 23 reviews

Cozy Cottage near Siesta Key Beach

Apr 8 – 15

G$32,844 GYD per night

Cottage in Bradenton

4.96 out of 5 average rating, 71 reviews

Adorable 1 bedroom close to IMG, AMI beaches

Oct 3 – 10

G$26,456 GYD per night

Cottage in Boca Grande

4.88 out of 5 average rating, 88 reviews

Charming beach cottage house with pool.

Sep 12 – 19

G$84,444 GYD per night

Cottage in Siesta Key

4.83 out of 5 average rating, 41 reviews

Awesome spot on Siesta Key - Walk to Everything!

Aug 13 – 20

G$40,977 GYD per night

Cottage in Bradenton

5.0 out of 5 average rating, 21 reviews

Seagull Cottage Cortez, Sleeps 6, Walk to Beach

Aug 24 – 31

G$35,065 GYD per night

Private cottage rentals

Cottage in Siesta Key

4.84 out of 5 average rating, 132 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Dec 26 – Jan 2

G$48,120 GYD per night

Cottage in Sarasota

4.84 out of 5 average rating, 154 reviews

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

Nov 24 – Dec 1

G$56,303 GYD per night

Cottage in Bokeelia

4.99 out of 5 average rating, 111 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Dec 24 – 31

G$43,956 GYD per night

Cottage in Siesta Key

4.81 out of 5 average rating, 260 reviews

Sunspot Cottage 2BR/2B Getaway w/ private beach

Sep 6 – 13

G$71,989 GYD per night

Cottage in Bradenton Beach

4.91 out of 5 average rating, 183 reviews

Ebb Tide @ Tides Inn

Sep 23 – 30

G$44,063 GYD per night

Cottage in Bradenton Beach

4.91 out of 5 average rating, 129 reviews

Historic Beach Cottage with private garden

Jul 8 – 15

G$62,158 GYD per night

Cottage in Sarasota

4.87 out of 5 average rating, 131 reviews

Charming Lido Cottage

Sep 22 – 29

G$62,974 GYD per night

Cottage in Sarasota

4.83 out of 5 average rating, 108 reviews

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

Apr 27 – May 4

G$54,007 GYD per night

Destinations to explore