Holiday rentals with breakfast in Siesta Key

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Tiny House Downtown St.Pete: Surprisingly Spacious

Tiny House is located only 3 blocks away from the Art District on Central Ave and John Hopkin's All Childrens. You will be impressed by how much space and storage Tiny House offers! The cozy decor invites you in to charming St. Petersburg with a warm sunshine filled hug. We have curated this Tiny Home for you all to enjoy St. Pete through local art and making this your home away from home. We hope you love our comfortable beds, various coffees, and our beautiful neighborhood. Adventure awaits!

Updated Nottingham Bungalow Near Siesta Key Beach

Book your Summer 2026 getaway - 30% off stays of 28+ nights. Pet-friendly Nottingham Beach Bungalow near the #1 rated - Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy a remodeled bath, stocked kitchen, T-Mobile 5G Wi-Fi, smart-lock self check-in, beach gear, assigned parking for 2 cars, private front-yard dining table & umbrella w/ seating for 4, & a charcoal grill. The shared fenced backyard w/ fire pit & propane grill. Best for 2; sleeps up to 4 to 6 with sleeper sofas.

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Spacious Suite Centrally Located Guest Favorite

You will fall in LOVE with area being so close to everything. Bright, open-concept design Suite with a complete kitchen, full bath, A/C, WiFi (100mbps), you have a private entrance and all amenities of home. New queen size bed. You are 15 min from St Pete Beach and 10 min to downtown St Pete. You have off street parking. Very safe and quiet location. Easy check in via lock box. You have beautiful gardens surrounding the property and Amazing deck. We have plenty of secret spots to recommend.

Apollo Beach is your getaway destination!

Receive a $25 gift card when you book this Tampa luxury private retreat. Just minutes from Apollo Beach Nature Reserve, Manatee Viewing Center, Downtown, Riverwalk, Busch Gardens, Florida Aquarium, & more! The perfect spot for family & friends, to relax or if you just want to enjoy a great chartered fishing trip sightseeing shopping and let's not forget our beautiful beaches Apollo Beach is just minutes from the interstates for quick easy access for whichever direction you want to travel

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

Historic Uptown 3/2 walkable to DT

Welcome to our newly renovated boho 2nd floor guesthouse in Historic Uptown. This 3 bedroom, 2 bath is an easy walk, bike, or short drive to St Pete downtown restaurants, bars, microbreweries, antique shops, museums, live entertainment and so much more. Central Ave is less than a mile and the beach is a 20 minute drive away. This centrally located, quiet, peaceful space includes Wi-Fi, 65" and 55" smart TVs, fully stocked kitchen, central air, and a zen inspired covered front porch.

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Peacock Way by Duncan Real Estate

Welcome to Peacock Way!This lovely 1 bedroom duplex side is tucked away on quiet Peacock Lane for a fantastic island getaway with a private pool. The ground level cottage style rental offers a spacious living area with fully equipped kitchen and bistro breakfast area. The property sleeps a total of 4 featuring the king bedroom and the living room sofa that can convert into a full size sleeper. Enjoy all new furnishings after the recent complete remodel!

Garage Mahal near downtown St. Petersburg, FL

Light, bright and brand spanking new St. Pete garage apartment located only a 5-minute drive from downtown restaurants, bars, entertainment scene, museums, major league baseball park and Tampa Bay waterfront. 15-minute drive to the Gulf Coast beaches rated tops in the US! Just 20-minutes from the Tampa airport. Includes in-unit washer and dryer, internet, and cableTV. Brand new central AC. Off-street parking and secure bike storage.

Perfect Location! Steps to Beach~Heated Pool!

Experience coastal luxury at Villa #2 Shrimp 🌴✨, a stylish studio just a 2-minute walk to Manatee Beach 🌊. Enjoy a king bed 👑, spa-like bath 🚿, kitchenette 🍽️, and a private tropical patio 🌿. Relax by the shared resort-style pool 💦, grill out 🍔, or explore nearby shops and dining 🚎🛍️. Dog friendly 🐾 with approval and includes 1 parking space 🚗—your perfect Anna Maria Island escape awaits!