Vacation rentals with a kayak in Holmes Beach

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Top-rated kayak rentals in Holmes Beach

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Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 477 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Aug 10 – 17

ﺩ.ﺇ406 per night

Guest favorite

Home in Longboat Key

4.87 out of 5 average rating, 106 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Nov 20 – 27

ﺩ.ﺇ2,155 per night

Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 152 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Nov 6 – 13

ﺩ.ﺇ1,994 per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Dec 14 – 21

ﺩ.ﺇ491 per night

Guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 407 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Oct 1 – 8

ﺩ.ﺇ530 per night

Guest favorite

Home in Ruskin

4.94 out of 5 average rating, 162 reviews

Private Beach Nature 2 ppl pets Work space remote

Unique, modern beachfront guest house-sits on a MULTI million $ property. Blend of Frank Lloyd Wright & Luis Barragan design. Located on Tampa Bay btwn Sarasota and Tampa/St Pete. Surrounded by palm trees, mangroves, birds chirping, dolphins, manatees, waves gently lapping and breezes. Sand from door to private beach. Fresh sheets, outdoor shower, small fridge, microwave, air fryer, & in and outdoor seating areas. Kayak and paddle board available. SUNRISE'S UNIQUE We are DOG FRIENDLY!

Jan 26 – Feb 2

ﺩ.ﺇ907 per night

Guest favorite

Guest suite in Largo

4.97 out of 5 average rating, 316 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee and tea. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Jul 30 – Aug 6

ﺩ.ﺇ432 per night

Superhost

Condo in Saint Petersburg

4.85 out of 5 average rating, 407 reviews

Waterfront condo on top floor @ Boca Ciega Resort

The view of water is fantastic. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking bay for the condominium guests or can stay indoors and enjoy puzzles and games. We have a kayak that can fit up to 2 adults for our guests to use.

Mar 21 – 28

ﺩ.ﺇ594 per night

Guest favorite

Home in Bradenton

4.92 out of 5 average rating, 118 reviews

Braden River Fishing Bungalow Oasis

Secluded bungalow situated on the Braden River, surrounded by a natural preserve. The river's hideaway is a real Floridian oasis, complete with a large deck that is directly on the river complete with outdoor furniture and grill. We supply everything for your Florida vacation, beach towels, chairs, toys & games. Just a few miles away are lots of shops, bars and restaurants for your enjoyment. We hope you love this oasis as much as our family and friends have.

May 3 – 10

ﺩ.ﺇ552 per night

Guest favorite

Guesthouse in Clearwater

4.98 out of 5 average rating, 191 reviews

Guest House close To Clearwater Beach

Welcome to Clearwater! Located just a short distance from a variety of restaurants, unique shops, and grocery stores, we offer convenient access to anything you might need during your stay. Our studio is 4 miles from Clearwater & 5 miles to Indian rocks Beach. There is no shortage of things to do in the area, local parks, museums, cruises, and a variety of nightlife. Enjoy jet skis, bike trails, tennis, parasailing, and pier fishing!

Jul 10 – 17

ﺩ.ﺇ428 per night

Guest favorite

Apartment in Clearwater

4.85 out of 5 average rating, 136 reviews

Bright & Beachy Studio 2 Blocks to Beach

Updated and welcoming Clearwater Beach studio apartment situated directly on the intracoastal waterfront. Quiet and centrally located neighborhood on the edge of residential and commercial districts, allowing for walking distance to everything on Clearwater Beach! Watersports on-site with office, offering amazing Island Jet ski tours, kayak & paddleboard rentals, parasailing!

Oct 14 – 21

ﺩ.ﺇ422 per night

Guest favorite

Apartment in Bradenton Beach

4.92 out of 5 average rating, 262 reviews

Las Palmas Beach Rentals unit 3

Las Palmas located on Anna Maria Island just steps to the Gulf of Mexico. Close to restaurants and shopping. Kayak, fishing, diving, nature trails, guided tours and more! Loads of adventure the challenge will be to just relax at the beach and catch the sunsets. We offer luggage drop off if you arrive prior to the unit being ready.

Aug 29 – Sep 5

ﺩ.ﺇ902 per night