Waterfront vacation rentals in Bay Pines

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Top-rated waterfront rentals in Bay Pines

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Saint Petersburg

4.99 out of 5 average rating, 246 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is close to Bay Pines VA Hospital, Madeira Beach, Tyrone Mall, Pinellas Trail, Bay Pines Park for biking and running, and restaurants. Wave runner, boat, kayak & paddle board rental available very nearby. There is a storage area for kayaks, paddle boards and bikes (please lock your items inside) . You’ll love my place because of the beautiful water view, peaceful good for the soul atmosphere and walkable to shopping, eating, and activities to suit all ages. Newly updated interior 2023.

Sep 10 – 17

G$41,957 GYD per night

Guest favorite

Apartment in Treasure Island

4.91 out of 5 average rating, 279 reviews

Attractive Beachfront Studio - Live Like a Local!

The true treasure of Treasure Island! Tucked right off of Gulf Blvd, on a secluded beach, this comfortable newly remodeled private studio is nestled on a lushly landscaped beachfront residential property with renters on-site. This cozy spot is all about barefoot luxury — you're just steps from the beach and biking or walking distance to laid back beach bars, live music & restaurants. Please note: There’s no guest parking available, but paid parking is nearby as well as a frequent public trolley.

Jul 23 – 30

G$29,211 GYD per night

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 112 reviews

"Sunsational" Indian Shores Getaway!

Updated studio perfect for your beach vacation! Great location with the Intercoastal Waterway in your backyard & access to the public beach right across the street in front! When you’re not soaking up the sun & sand, you’ll appreciate the community amenities which include the second largest pool (not heated) on all the barrier islands, boat slips, picnic tables/bbq area, and shuffleboard. The second floor studio is comfortable and equipped with everything you’ll need…just bring your sunscreen!

Jul 17 – 24

G$33,679 GYD per night

Guest favorite

Condo in Treasure Island

4.95 out of 5 average rating, 136 reviews

Exquisite, Modern Waterfront Condo, A Hidden Gem!

Sip coffee in the seating area, read a book by the pool, or enjoy a drink on the beach! Beautifully renovated, second-floor waterfront condo in Treasure Island, 2 blocks from the beach. A short walk to restaurants & shopping includes everything you need to enjoy your vacation. The condo offers high-speed internet, a full kitchen with all cooking needs, 65" Wi-Fi TV, Netflix, a community grill/pool washer/dryer, and free parking steps away. Close to Downtown St Petersburg, Clearwater & Tampa.

Nov 1 – 8

G$36,725 GYD per night

Guest favorite

Home in Largo

4.96 out of 5 average rating, 102 reviews

Stars by the Sea - Cozy home close to beaches

Our home is beautifully updated, fully furnished and decorated in a beach theme. The master bedroom has a comfortable king size bed and the second bedroom has a queen. We have a beautiful pond in the back. Perfect for you to relax and BBQ while enjoying our wonderful Florida weather. The house has a Smart TV, Internet w/Wi-Fi, dishwasher, washer, dryer, and much more. Everything you need to make your stay perfect. We are close to great shopping, dining and to some of Florida's best beaches.

Nov 26 – Dec 3

G$28,343 GYD per night

Guest favorite

Home in St. Petersburg

4.98 out of 5 average rating, 130 reviews

SPARKLING HOT Modern Pool Home- Minutes to beach!

FLAWLESS HOME with a dream kitchen! Just an 8 min. drive to the beaches! Home has 4BR/3BA which includes the poolside guest bungalow. A stunning saltwater pool overlooking a small lake full of wildlife. Smart televisions everywhere in this home and WIFI is included. The decor is a real showstopper! Family neighborhood near dining, shopping, Walmart and beaches! This home is professionally and immaculately cleaned before every guest. Heated pool OPTION is available for additional cost.

Nov 11 – 18

G$86,198 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 238 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.

May 26 – 31

G$26,241 GYD per night

Superhost

Condo in Madeira Beach

4.87 out of 5 average rating, 180 reviews

Beach is steps away! Paradise is waiting!

Our little slice of paradise: 1 bedroom ground floor condo in Madeira Beach Yacht Club. 2 heated pools, gym, jacuzzi, & fishing piers. Across from a Park with tennis courts, basketball, & walking trails. Grocery, CVS, restaurants and bars in walking distance. Beach toys & beach cart provided for you to enjoy the white sands of Madeira Beach, a few steps away. Our charming beach community has plenty of attractions and activities with small-town charm. Just minutes from John's Pass!

Nov 12 – 19

G$31,507 GYD per night

Guest favorite

Apartment in Saint Petersburg

4.89 out of 5 average rating, 145 reviews

The Oasis

Welcome to Boca Ciega Oasis! The "Oasis" suite 409 has been totally remodeled in January 2022. This includes a new queen sofa couch in LR, new refrigerator, stove, washer/dryer, and balcony tables and chairs. The 4th-floor view is the best but 409 is also centered beautifully to take in the expansive Boca Ciega Bay! Directly below the balcony is the swimming pool, Hot tub, and observation pier! The marina is to your left. See all while sitting in our bar height chairs and tables.

Apr 25 – May 2

G$31,359 GYD per night

Superhost

Condo in Treasure Island

4.88 out of 5 average rating, 168 reviews

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

Oct 12 – 19

G$116,878 GYD per night

Superhost

Apartment in Madeira Beach

4.81 out of 5 average rating, 330 reviews

Blue Octopus~Walk 2 beach & Johns Pass~King Bed

Enjoy old Florida Charm at this refreshed (Dec 22) fishing village apartment with views of the canal and "mini marina" filled with fishing boats and the occasional dolphin! 100 yard walk to Johns Pass, stroll the board walk full of restaurants, shops and water sports. Grab some ice cream and walk to the beach (5-10 mins)for the sunset! You can’t beat this location!*King bed* sleeper sofa*equipped kitchen*fast wifi*2 Smart TVs*Waterfront docks and a designated parking space!

Jul 15 – 22

G$29,143 GYD per night

Guest favorite

Condo in Madeira Beach

4.93 out of 5 average rating, 123 reviews

Sunsets in Paradise from Balcony with Gulf Views

The new pool is now open, featuring a sun shelf! Stunning views of the Gulf of Mexico from this beautiful and modern 5th floor condo! This highly rated vacation or relaxation destination is perfectly situated just steps away from the beach in Madeira. You will enjoy your private balcony, a 2 bed/2bath space, community pool and proximity to everything. We offer high speed internet, beach equipment, towels and linens and everything you would need to enjoy your stay. Welcome!

Aug 11 – 18

G$40,513 GYD per night