Holiday rentals with a kayak in Siesta Key

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Top-rated rentals with kayak in Siesta Key

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Guest favourite

Apartment in Nokomis

5 out of 5 average rating, 42 reviews

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

Superhost

Apartment in Bradenton

5 out of 5 average rating, 3 reviews

Intracoastal Connections-Incredible Sunsets-Luxury

Experience waterfront luxury at this stunning 3-bed, 3-bath gem in Marina Walk, One Particular Harbor. Just 1.8 miles from Anna Maria Island's beaches, this home offers breathtaking views of Anna Maria Sound. Monthly guests enjoy resort pools, fitness center, nature trails, kayaking, and Sky Bar. Short-term visitors access the pool, splash park, and BBQ areas. Relax on the lanai, savor sunsets, or explore local attractions. Fully equipped with beach essentials, it’s your perfect coastal escape!

Guest favourite

Home in Ruskin

4.93 out of 5 average rating, 72 reviews

Silverking Keys Retreat!

Come stay and play at this beautiful 2 bedroom 2 bathroom house (only 1st story) located right on the Tampa Bay! It faces downtown Tampa and St. Petersburg. You can cook breakfast and view the bay straight from the kitchen dinette. The property is located on a dead end street. Fish, and star-gaze from two private docks, one being a two-story. Fish, kayak, snorkel, and you can bring your own boat! A natural sanctuary for dolphins, manatees, red fish, blue herring, snook, ospreys, and eagles!

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 17 reviews

Beautiful MidCentury Modern Home

Our charming 2BR/2Bath mid-century modern home just steps from the water. Explore Sarasota's beautiful mangroves and beaches with our kayak or bicycle to nearby attractions. Enjoy the open floor plan, modern kitchen, and comfortable living room with sectional couch and TV. The primary bedroom offers a queen bed and office space. The second bedroom has a full bed and TV. Recently remodeled bathrooms and a separate laundry room add convenience. Siesta Key Beach is only six miles away. No pets.

Guest favourite

Apartment in Sarasota

5 out of 5 average rating, 23 reviews

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

This unique 2 bedroom/ 2 bath condo is right on the waterfront in Siesta Key! It is the upper condo of a two story complex that has a perfect view and feels like your own personal getaway! It comes with a full kitchen, living room, and two decks. Part of what makes it amazing is the private dock on the Pass. Perfect for kayaking and exploring! Or maybe you'd like to just relax and take a dip in the heated pool? Located in the quiet end, you can enjoy the calm, or head to Siesta Village!

Guest favourite

Tiny home in Sarasota

4.96 out of 5 average rating, 330 reviews

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Guest favourite

Houseboat in Palmetto

4.88 out of 5 average rating, 17 reviews

Serenity with Kayaks Fishing Beach Gear & Sunsets

Escape to tranquility and experience the magic of life on the water. Whether you're seeking relaxation, adventure, or a bit of both, we welcome you with open arms. Let the gentle waves, fresh sea breeze, and waterfront views create the perfect getaway. Living the dream has never been this easy! Come aboard and make unforgettable memories. ⚓ 📢 Special Offer: * First two nights—No cleaning fee! * After three nights—$75 cleaning fee applies. Book your stay and let the adventure begin!

Guest favourite

Home in Bradenton

5 out of 5 average rating, 26 reviews

Waterfront/Kayak with Manatees/Pool/Fish

Relax with the whole family at this peaceful home on a natural waterway/cove with saltwater pool, bikes, kayaks & firepit! Lots of wildlife, water fowl, manatees, turtles & flying fish. This home is completely remodeled with the most modern & best features. This home has 3 Bedrooms, 2 Spa Baths & a Queen sleeper sofa in a open, spacious floor plan with cathedral ceilings. On the Sarasota/Bradenton border, conveniences are just blocks away & beaches & airport are a short drive away.

Superhost

Townhouse in Sarasota

4.78 out of 5 average rating, 139 reviews

Peaceful Oasis: King Bed & Incredible Views

You have arrived, upon entering you will go upstairs to your spacious duplex. You will be greeted by an amazing view of the intercoastal waterway. You will love kayaking on the waterway & seeing all the amazing wildlife. You can sit on your downstairs patio with a cup of coffee or you can take a stroll to Turtle Beach & enjoy the sunset. Hop aboard the trolley & go to the Village & eat and drink at one of our famous restaurants or one of our favorite hot spots. See Guidebook.

Guest favourite

Home in Venice

4.95 out of 5 average rating, 134 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Welcome to our Mid Century Modern waterfront getaway on the highly sought after Curry Creek. Perfectly situation between Nokomis Beach (2 miles) and Venice Beach (3 miles). Enjoy spending time fishing on the private dock or getting out on the water with our 4 kayaks and slip. We're located a half mile away from The Legacy Bike Trail (we have 6 bikes for guest use). large firepit, charcoal grill, cornhole, tons of supplies for shark teeth hunting and days spent at the beach

Guest favourite

Home in Bradenton

5 out of 5 average rating, 81 reviews

River House with Kayaks. Relax on the River.

Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.

Superhost

Townhouse in Ruskin

4.94 out of 5 average rating, 222 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.