Ski-in/Ski-out holiday rentals in Hillsborough County

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals in Hillsborough County

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Home in INDIAN RK BCH

4.67 out of 5 average rating, 15 reviews

Beach Waterfront 5*star Location Indian Rocks Bch

INTRACOASTAL WATERFRONT HOUSE & DOCK with BEACH ACCESS. Florida room with French Doors and windows gives 270 degree views of the waterfront. You'll feel like your you're on a yacht! Enjoy watching the boats go by lounging on the hammock. Private yard with dining table and plenty of chairs and lounges for your guests. Stocked with books & games. Walk, Bike or Trolley everywhere. The Key Lime Cottage Indian Rocks Beach and JD's Restaurant and Tiki Bar are infamous to our regular vacationers.

Tiny home in Anna Maria

4.62 out of 5 average rating, 29 reviews

Villa la Esperanza Jacaranda Cottage

Beach cottage on Anna Maria Island. This unique living space can house up to 4 guest providing 1 queen size bed and 2 bunk beds. It's designed to provide privacy for the guest even in a cozy space. Only a few steps from the beach you can e on the soft Anna Maria sand within 5 minutes. The main house will not be used while the cottage is rented so feel free to enjoy the Olympic sized pool as well as the boat dock with lift. Get all the amenities this house has to offer at an affordable price.

Guest favourite

Guest suite in Tampa

4.89 out of 5 average rating, 139 reviews

Tranquil Tampa Hideaway

This memorable place is anything but ordinary. This hideaway is fully equipped with 1 queen bed, a full bathroom, and a coffee machine. It comes with dinnerware, silverware, cookware, extra towels, and toiletries. Tampa International Airport - 10 minutes away Downtown Tampa + Ybor City - 20 minutes away Zoo Tampa - 20 minutes away Florida Aquarium - 25 minutes away Busch Gardens + Adventure Island - 30 minutes away Clearwater Beach + St. Pete Beach - 40 minutes away Wifi is included.

Home in Anna Maria

Rainbow Reef: Near Bean Point, Pool, Game Room

Rainbow Reef by Anna Maria Life Vacation Rentals 720 Holly Rd, Anna Maria, FL 34216 What You'll Love About This Home: Location! 2 Blocks to the Beach! 5 Bedrooms / 3 Bathrooms 2 Kings, 1 Queen, 4 Fulls Private Pool Pool Loungers & Umbrellas Gas Grill Patio Dining for 6 Hammock Ping Pong, Foos Ball, Pool Table Professional Linen Service, Washer & Dryer Complimentary WIFI Beach Towels, Beach Chairs, Beach Wagon Parking for 3 Cars VR16-000153

Superhost

Home in Largo

New place to stay

2035 SqFt | King Bds | BBQ | W/D | No C/O Instr

Spacious 4BR/4BA coastal oasis in Largo, FL! This stylish waterfront home sleeps 10 and features a private screened pool, modern kitchen, and bright open living spaces. Enjoy outdoor dining, a propane grill, and a small dock for fishing or water sports. Ideal for families or groups, with king beds, bunk room, ensuite baths, and family-friendly extras like a Pack N Play and high chair. Minutes to beaches, dining, and Tampa Bay attractions!

Home in Tampa

4.65 out of 5 average rating, 82 reviews

Beautiful New Home Near Ybor and Downtown

Relax with the whole family at this peaceful place to stay with New House Enjoy staying in the heart of Historic Ybor City with all the modern amenities, enjoy visiting downtown Tampa, the Riverwalk, Raymond James Stadium, Channelside Cruise port, Armature Works, Amphitheatre, Casino Busch Garden, Tampa Zoo International Airport, University, beaches and more!