Bungalow vacation rentals in Siesta Key

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Top-rated bungalow rentals in Siesta Key

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

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Guest favourite

Bungalow in Sarasota

4.92 out of 5 average rating, 309 reviews

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with cypress wood floors and lots of natural light, located in a quiet neighbourhood on the downtown core edge. Enjoy a spacious and fenced in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

Jan. 27 – Feb. 3

$377 CAD per night

Guest favourite

Bungalow in Sarasota

4.94 out of 5 average rating, 127 reviews

West of Trail Home Near SMH, Siesta & Lido Key

This renovated, mid-century home - rarely available in Cherokee Park/West of Trail area - is safely situated among multi-million dollar homes and gorgeous large oaks. No need for a car with biking distance to Siesta Key, downtown Sarasota, Sarasota Memorial Hospital and Bayfront Park. Walk to Southside Village shops & restaurants, or Selby Gardens. Take a stroll in this walkable neighborhood to see the sun set over the water down the street. This 2/2 home makes for the vacation of a lifetime.

Oct. 15 – 22

$570 CAD per night

Guest favourite

Bungalow in Bradenton

4.95 out of 5 average rating, 102 reviews

Sugar Sand Cottage

Charming 2 Bedroom, 1 Bath bungalow centrally located in Sunny Bradenton Florida. The Sugar Sand Cottage is 8.4 miles from the beach! Anna Maria Island, Coquina, and Manatee Beaches are some of the best beaches! The downtown life is 2 miles away. The bus stop is less than a quarter mile away. Watch Spring Training at LECOM PARK which is 0.9 miles away. PUBLIX is 1.9 miles away. Walmart is 3.3 miles away. I follow cleaning guidelines set by Airbnb between stays for your security and comfort!

Dec. 20 – 27

$316 CAD per night

Guest favourite

Bungalow in Sarasota

4.81 out of 5 average rating, 129 reviews

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

This wonderful pool home is located in the heart of Sarasota and just minutes away from the world-famous Siesta Key Beach! This fantastic vacation home offers 4 relaxing bedrooms and 3 full baths - there is also a Queen-size pull out sofa in the living room. A real bonus is having two master suites! The first offers a King-size bed with an adjoining bathroom featuring a walk-in shower plus his & her sinks. The second master is appointed with a Queen-sized bed and adjoining bathroom.

Oct. 27 – Nov. 3

$510 CAD per night

Guest favourite

Bungalow in Anna Maria

4.88 out of 5 average rating, 121 reviews

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Apr. 14 – 21

$625 CAD per night

Guest favourite

Bungalow in Gulfport

4.96 out of 5 average rating, 154 reviews

Gulfport - St. Pete bungalow centrally located

Cozy and private apartment perfectly situated between St Pete Beaches, downtown St. Petersburg, and the quirky vibrant downtown Gulfport Arts District. This is a private apartment with 2 rooms, 1 bath, kitchenette, and patio. We live on the property in the other side of the Duplex, but your suite is completely private with your own entrance. Nature Park & bike trails: down the street! Downtown gulfport: 1mi / 3min St. Pete beach 4.6mi / 10min Downtown St Pete : 5mi / 10min

Feb. 7 – 14

$235 CAD per night

Guest favourite

Bungalow in Osprey

4.77 out of 5 average rating, 319 reviews

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

Floridian Tiny Cottage! Buttonwood Cottage is wonderfully located central to the downtowns and beaches of Sarasota and Venice with a private patio space and hot tub. 15 minutes away for the number 1 beach in USA "Siesta Key" . You'll feel that you stepped back in time upon arrival to our charming homestead. I follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights:

Jul. 14 – 21

$199 CAD per night

Guest favourite

Bungalow in Englewood

4.96 out of 5 average rating, 169 reviews

TROPICAL OASIS, MINUTES FROM THE BEACH!!

This charming 2 bedroom/2 bathroom, dog friendly home in Englewood is located 2 miles away from our beautiful Manasota Beach. Call this your home away from home, as you will find a flat screen TV, Dish, free wireless internet and a gas grill, washer/dryer, and a fully equipped kitchen. Bring your boat (boat ramp is located in the neighborhood), bathing suits, beach towels and sunscreen. We have the rest ready for you.

Oct. 15 – 22

$199 CAD per night

Superhost

Bungalow in Gulfport

4.9 out of 5 average rating, 124 reviews

Jackie O Suite/1 block to shops/Restaurants

The Jackie O is an elegantly decorated apartment with-in walking distance to the beach and downtown amenities of Gulfport FL. Enjoy local jazz music in town and Tuesday markets for finding unique items. The locals will make you feel like one of them and the beach will soothe your soul. We try to provide everything you will need for your comfort and will respond immediately with any issues or concerns.

Jun. 22 – 29

$231 CAD per night

Guest favourite

Bungalow in Sarasota

4.97 out of 5 average rating, 172 reviews

The Sarasota Sea Turtle Cottage

Paradise found at the private Cottage in a lush and quiet area with modern amenities and decor that feels artistic and comfortable -- all at once. The location is sublime -- walking distance to vibrant downtown SRQ & short car-ride to the beach. Please see our newest luxury accommodations "The Mermaids & Corkscrew Loft". http://abnb.me/EVmg/rt4iVIO3cF.

Jul. 30 – Aug. 6

$200 CAD per night

Guest favourite

Bungalow in Sarasota

4.98 out of 5 average rating, 59 reviews

*Waterfront house with dock and heated pool

Bring your boat! Sandy Crab Retreat is a fresh, clean, chic beach house located on Philippi Creek! Newly updated three bedroom, two bathroom with a POOL & dock to fish. We are located 1.5 miles from Siesta Key, the #1 beach in USA, and only 10 mins from downtown. Lots of shopping, restaurants, and outdoor activities.

Sep. 1 – 8

$486 CAD per night

Guest favourite

Bungalow in Gulfport

4.9 out of 5 average rating, 164 reviews

Historic Gulfport Charmer

This home is a classic 1920's Florida Craftsman style bungalow. In the heart of historic downtown Gulfport, it is half a block from fabulous dining, unique boutiques and beautiful Boca Ciega bay. Just a short drive to white sand Gulf coast beaches and hip artsy St Petersburg. Dogs are welcome $100 fee.

Oct. 21 – 28

$248 CAD per night