Family-friendly holiday rentals in Harbour Island

Davis Islands' Historical Gem

Enjoy a 5 star hideaway on the grounds of an original 1926 Davis Islands home. This second-floor vintage space oozes charm and history. Living room with open kitchen area, spacious bedroom with queen bed, and walk-in closet—all with gleaming hardwood floors. Original cedar-paneled walls & ceilings in bedroom and bath. Marble floor and shower in bathroom. Relaxing balcony with privacy curtains, dining table & glider chairs. Apartment is totally separate from the family home. Private & safe.

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

Pool Side Getaway, Walk/Bike Tampa River Walk

Experience Tampa from our little slice of Heaven right in the heart of Tampa Heights. This is a detached private Pool House in our backyard. At 264 sqft, It has a full Bath, Kitchen, and studio space with a Queen memory foam mattress, and work space / breakfast table. Enjoy the Pool and its tropical surroundings or just relax in a lounge chair. We are walking distance to Lee’s Pizza, Armature Works, River Walk, and much more... Included is a smart TV, WIFI, and Two Bicycles to go explore.

Charming private guest house.

Our charming one bedroom guest cottage on Davis Islands sleeps 2 (queen-sized bed). Bathroom with large shower. Clean and cozy room has cable tv, wi-fi, mini fridge, microwave, Keurig coffee maker. Gorgeous neighborhood, walking distance to downtown DI restaurants, coffee shops, rentable bikes, Amalie Arena, the Riverwalk, Hyde Park, downtown Tampa, the Convention Center, Channelside & TGH. 2 miles from cruise port. 15 min. drive to Bush Gardens. Enjoy the sunset at the end of the island.

Now Reopened! - The Highland Hideaway

Enjoy our beautiful guest house privately for up to two guests. Perfect for the solo traveller or couple looking to see and do the best Tampa has to offer! Located less than 15 minutes from the Tampa River Walk, Downtown Tampa and Ybor City, and less than 10 minutes from Busch Gardens Amusement Park and the famous Zoo Tampa, your options are many. From restaurants to kayaking, bike trails to BBQs... We welcome you to find your peace (or adventure) as you nestle in at The Highland Hideaway.

Newly Built Above-Garage Apartment near Downtown

Enjoy walking to the best Tampa has to offer! Walking times: -> 10-15 minutes to Armature Works, The Riverwalk, breweries, and coffee shops -> 25 minutes to Ybor City -> 40 minutes to the Convention Center, or an 8-minute Uber ride Built in 2021, this above-garage studio unit is modern and clean, with high-quality finishes including real wood floors, marble countertops, and a 60" TV. The wet bar makes it easy to enjoy your morning coffee or evening wine on the patio or in the reading nook.

Tiny House Oasis Blue Vatican . Near MacDill Base

Enjoy this small and beautiful Oasis, a perfect hideaway to forget about the noise of the city, relax with the aroma diffusers and your favorite music; In the mornings fall in love with our solarium while having a good coffee. We are located in South Tampa just 3 minutes away from the MacDill Airbase. 5 min Picnic Island Park, 10 min Port Tampa Bay Cruise and Downtown, 15 min International Airport. 15 min Raymond James Stadium, 40 min Clearwater Beach. Free Parking for up to 2 cars.

cute comfy & cozy 2nd Floor Guest Suite (Seashell)

Welcome to my 400sqf one bedroom second floor Mother-In-Law private guest suite. Its very cute and cozy. Once you come up the stairs, you will find a deck with outside sitting to enjoy the great Florida weather. Inside there is a full kitchen with everything you need to cook a meal and relax on the sofa and watch some streaming shows before heading to your even or wonder around ybor city or down town. My place is in a neighborhood about 1-4 miles from most of what Tampa has to offer.

King Bed~ Stylish, Bright & Cozy 4 min to Downtown

Discover the perfect blend of style, comfort, and convenience at our 3BR 3Bath Tampa Heights Oasis, a gem nestled in the city's heart, just minutes from Downtown Tampa. This vibrant neighborhood boasts excellent restaurants, shops, attractions, and landmarks, making it an ideal base for your Tampa getaway. ✔ 3 Cozy Bedrooms w/ Premium Bedding ✔ Open Concept Living Area ✔ Fully Equipped Gourmet Kitchen ✔ Smart TVs ✔ Fast Wi-Fi (300 Mbps) ✔ In-Unit Washer/Dryer ✔ Free Parking

Boho-Inspired Retreat • Close to Downtown & Ybor

Make yourself at home in this cozy 2-bedroom, 1-bath apartment featuring a full kitchen and in-unit washer and dryer—perfect for a weekend escape, a weeklong stay, or an extended trip. Located in Palmetto Beach, one of Tampa’s historic neighborhoods, this home is just minutes from iconic spots like Ybor City, Channelside, Amalie Arena, the Tampa Convention Center, and much more. Whether you're here for business, a concert, or just to explore, this is your perfect home base.

Private Studio w/Free Parking Walk to Bucs Stadium

Charming private studio just minutes from Raymond James Stadium. Enjoy a private entrance, furnished outdoor area, kitchenette, A/C, smart TV, and free parking(for 2spots). Perfect for business or leisure travelers attending local events. Conveniently located near the airport and downtown. Relax in a quiet, well-equipped space with self check-in, fresh linens, coffee, and all the essentials for a pleasant stay. Great location, safe neighborhood, and fast Wi-Fi included.

Sonia's Little House

Welcome to your perfect home base in Tampa! This charming and private efficiency unit offers everything you need for a comfortable stay—whether you're visiting for business, vacation, or an extended stay. Located in a quiet residential neighborhood just minutes from downtown Tampa, Raymond James Stadium, Midtown, and Tampa International Airport, you'll enjoy easy access to all the city’s highlights while coming home to a peaceful retreat.