Vacation rentals with a kayak in Gulfport

Sunny PaG Island rental w/bikes-just steps2beach

Welcome to your beach getaway! This cheerful, sun-soaked cottage is steps from the sand—or your next ice cream or seaside meal at a nearby restaurant. Perfect for couples or solo travelers, a comfy queen bed, a breezy living room, and a kitchen and dining area. Sip your morning drink on the upstairs porch as salty breezes drift by, or fire up the BBQ on the downstairs patio. Two bikes are yours to cruise the island like a local—Everything you need for a relaxing, joy-filled beach escape is here

Central Bungalow Near DTSP with Swim Spa

Vacation like a local at this centrally located bungalow style residence. This 3BR 2 Bath home is set to entertain our guests. Indoor living space Includes two sitting areas, fireplace and workstation. The dining room and kitchen welcomes you home with all the amenities you need to keep everyone happy. For our outdoor lovers, we welcome you to the tavern. This fully functional outdoor living space includes a grill, tv, sectional seating, full size bar. Be our guest and enjoy St Pete like a local

Waterfront tiny in St Petersburg - The ‘V’

The ‘V’ is your perfect getaway to make fun memories. Note: You MUST have a 5 star rating on airbnb ! Take yourself back to the good old days of simplicity and relaxation. Paddle-board from your own private mangrove beach through the canals and to Tampa Bay. Experience dolphins swiming along side you, manatees feeding on sea grass or baby sharks out by the sandbar just 200 yards from the beach. The ‘V’ rests in a culd-de-sac in a quiet waterfront neighborhood just 10 minutes south of DT.

Coral Reef~90° Heated Pool~Remodeled~2 min 2 beach

LOCATION! LOCATION! LOCATION! Completely renovated vacation rental located 1.5 blocks to the beautiful beach & across the street from Brown Park. This unit is located on the 2nd floor of a small two story building w/ 4 units. Out back is a large HEATED pool, lounge chairs, a dining table, grill, surfboard shower, fire pit and more. Walk two minutes down a beautiful palm tree lined path to the beach! We provide you w/ all your beach needs, towels, umbrella, beach chairs, floats and much more!

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam king bed & secured safe.

Walk score 82 | bikes | kayak | 214mbps | foam bed

♡ 400ft²/38m² private craftsman studio apartment on shared property ♡ ☞ Walk Score 82 (walk to cafes, dining, shopping..) ☞ Bike Score 75 (2 bikes provided) ☞ Memory foam mattress + sofa couch ☞ Fully equipped + stocked kitchen (K-cup) ☞ Free kayaks + beach gear ☞ Onsite parking ☞ Smart TV w/ Netflix ☞ 214Mbps Wi-Fi ☞ AC & Heat 5 min → Salvador Dall Museum, Vinoy Park, St. Pete Pier 15 min → Airport & St Pete Beach ***Send me a message for current promos***

Key Rossman

A familiar taste of the Florida Keys, right in the heart of St. Petersburg. Peacefully and centrally located to coastal views, downtown Gulfport and St. Pete. Relax by the camp fire or cruise on down the Pinellas Bike Trail. We have everything you need for your sunny getaway within reach. Whether chasing the night life , enjoying the Florida scenery or having a cocktail at a tiki bar is your thing, you'll love it here at Key Rossman!

Beachy Bayfront Condo Walk to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

Florida Gulf Coast Luxury Oasis

This newly-renovated property features all new appliances and wood-effect porcelain tile floors throughout. Elegantly and expertly furnished, this house is as cozy and comfortable as it is luxurious, boasting all-cotton bedding and bath towels as well as a 55-inch flat screen smart TV with plenty of free streaming options. As for location, Gulfport is conveniently located between downtown St Pete and the Gulf of Mexico beaches.

Waterfront condo on top floor @ Boca Ciega Resort

Great view of water. 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 the intercoastal or stay indoors and enjoy puzzles and games.