Holiday rentals in Bay Pines

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Top-rated holiday rentals in Bay Pines

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

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Top guest favourite
A bright orange sofa is arranged in a welcoming living area featuring decorative pillows and a neon sign reading 'A Bit Beachy.' Two table lamps provide soft lighting beside the sofa, and colorful oars are displayed on the wall above, enhancing the beach-themed decor.
Home in St. Petersburg
4.92 out of 5 average rating, 36 reviews

Spacious and Short Drive to Beach

Nestled in the heart of Bay Pines, Florida, our retreat offers a relaxing family getaway for a fun-filled vacation, being an ideal spot to create unforgettable memories. Our home boasts a central location, just minutes from Gulf beaches, local attractions, and dining/shopping options. Explore nearby parks, catch a sunset at Madeira Beach, or take a short drive to the famous John’s Pass Village & Boardwalk. Our home features spacious living areas, a fully equipped kitchen, and a private backyard.

Top guest favourite
A spacious living area features a large TV mounted on a green accent wall, complemented by wooden flooring. Natural light enters through a window adorned with flowing curtains. A coffee table sits at the center, surrounded by comfortable seating and a decorative plant.
Home in St. Petersburg
4.95 out of 5 average rating, 124 reviews

Charming Of Sand and Sea Home

Make yourself at home in this charming and relaxed house in a quiet family neighborhood. Every detail has been thought out with brand new modern furnishings. The living/dining/kitchen area is spacious with lots of natural light, and can easily accommodate 4-8 guests. A stocked kitchen is open to the living & dining areas equipped with refrigerator and dish washer. There is a full-size washer and dryer. All bed/bath/kitchen/beach linens are supplied. Large driveway available for free parking.

Guest favourite
An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.
Villa in St. Petersburg
4.95 out of 5 average rating, 150 reviews

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Top guest favourite
Home in St. Petersburg
4.96 out of 5 average rating, 239 reviews

Surf’s UP! Pool, Cabana & Poolside bungalow!

Presented by "ST PETE VACATION HOMES". Explore our 15 Airbnb homes online or on our Airbnb profile. Home sleeps 8 guests. OUTDOOR FEATURES: * adorable guest bungalow * saltwater pool w/ optional heater * large tiki hut w/ lounge seating, TV & beverage fridge * lounge seating w/ TV * bar top seating * propane grill * tropical foliage LOCATION: • madeira beach ~6 minutes • walmart, dining + coffee ~1 minute WALK!😇 • john’s pass village & boardwalk~10 minutes • downtown st. pete ~25 minutes

Guest favourite
Home in St. Petersburg
4.97 out of 5 average rating, 177 reviews

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Kick back and relax in this calm, stylish beach-vibin home. The 2 bedroom plus queen size sleeper sofa in sunroom is the perfect spot to get away and never have to leave. Enjoy your morning coffee or afternoon cocktail lounging by the fire pit. Light up the grill and cook your meal while you enjoy a pool heated to 86 degrees for free! Wifi and 3 streaming TV's. If you want to get out and explore, you are only 6 minutes from the award winning beaches and 25 minutes from downtown St Pete.

Top guest favourite
A private outdoor deck is shown with a mix of seating areas. A cozy sectional sofa is paired with square coffee tables, surrounded by decorative chairs. A large umbrella provides shade, while a tree adds a natural element to the space, creating an inviting area for relaxation.
Guest house in Seminole
4.92 out of 5 average rating, 141 reviews

Beachy Bohemian Bungalow with all the perks!

This cozy spot sits in a quiet neighborhood that boasts access to the Pinellas Trail Bike rental close Full kitchen w/ extras Queen bed w/ built in drawers Shelves & clothing rack Smart TV Full bath w/ walk-in shower Ample outlets/ USB Private deck for sun & shade Beach chairs, towels etc for beach Convenient to a dozen parks, beaches, shopping & restaurants. 2 miles to Madeira Beach 3 m - Johns Pass 1.2 m - Seminole City Center 7.6 m - St. Pete/ Clearwater Airport NO SMOKING NO PETS

Top guest favourite
A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.
Home in St. Petersburg
5 out of 5 average rating, 217 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Top guest favourite
Flat in St. Petersburg
4.97 out of 5 average rating, 155 reviews

Coastal Retreat Near Madeira Beach With Game Room

This 2-bedroom unit with a bonus Game Room and Sunroom is the perfect getaway for up to 6 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cul-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive (3.7 miles) to the famous John's Pass Village and Boardwalk.

Guest favourite
A spacious eat-in kitchen is shown with modern cabinetry and stainless steel appliances. A round dining table with four chairs is positioned near a large window. The countertop features bar seating with three stools, and a small potted plant adds a touch of greenery.
Home in St. Petersburg
5 out of 5 average rating, 32 reviews

Bliss on the Bay, Bay Pines, St. Petersburg, FL US

Peaceful and private 1500 square foot, fully furnished 3 BR/2 Bath home in a quiet neighborhood with a 5 minute drive to Madeira Beach. Beautiful kitchen and baths along with an amazing outdoor space which includes a heated, in ground pool, gazebo covered patio and a BBQ grill. The neighborhood has quick access to the Pinellas (walking/biking) Trail. Other amenities include: HVAC, fully equipped kitchen, bath/beach/pool accessories. Just move in and enjoy your stay!

Guest favourite
The living area features a comfortable couch and a cozy sleeper sofa, accompanied by a round coffee table at the center. Soft, ambient light enters through large windows, with light-colored curtains providing a relaxed feel. A side chair and a console enhance the inviting layout.
Home in St. Petersburg
4.9 out of 5 average rating, 81 reviews

2BR home near Madeira Beach, Florida

This quaint home is near world-class beaches and offers a peaceful stay. Enjoy proximity to many wonderful events, restaurants, and shops in the Tampa Bay area. A fully equipped kitchen allows you to enjoy meals on the screened lanai. A porch swing lets you relax with the sea breezes on the front porch. The sandy shores of Madeira Beach are just 6 minutes by car and waterfront restaurants and recreation at John's Pass are just 5 minutes further South.

Guest favourite
Home in St. Petersburg
4.91 out of 5 average rating, 44 reviews

Palm Oasis 2/2 Serene Backyard Private Poolside

Vista Luxury Vacation Rentals Create memories with your loved ones or new friends in this Huge Backyard two-bedroom, two-bath pool house. Relax and have your memories start in this mid-century contemporary home. The house is a one-level home, there are no steps inside the house. There is one step at the entrance to the house's main door and garage door going to the laundry/second bathroom. The best of all is HUGE BACKYARD FULLY FENCED with Pool.

Guest favourite
Home in St. Petersburg
5 out of 5 average rating, 27 reviews

Madeira Beach Pool Home w/Guest House

Freshly renovated coastal retreat just 1.5 miles from Madeira & Redington beaches! The main home offers bright, modern spaces while the attached guest house features its own kitchen, bedroom & bath—perfect for family or friends. Enjoy a private heated pool, fully fenced yard & outdoor dining area, all designed for relaxation and fun. Family-friendly, stylish, and close to beaches, dining & shopping. Pets stay free.

Popular amenities for Bay Pines holiday rentals

When is the best time to visit Bay Pines?

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Avg. price$232 SGD$281 SGD$320 SGD$263 SGD$231 SGD$239 SGD$250 SGD$210 SGD$187 SGD$193 SGD$200 SGD$236 SGD
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

Frequently Asked Questions

  • What are the best places to stay in Bay Pines?

    Accommodations around residential neighborhoods in Bay Pines provide quiet, comfortable stays close to marinas and parks. Many visitors choose vacation rentals with outdoor spaces and access to local amenities.

  • What are the best things to do in Bay Pines with kids?

    Kids enjoy parks with play areas and waterfront activities like paddleboarding, fishing, or shell collecting. The nearby region also has interactive museums and aquariums that families often visit on rainy days.

  • What are some of the best things to do in Bay Pines?

    Explore marina areas, enjoy fresh seafood in local restaurants, or stroll through parks with scenic water views. Cultural history and outdoor activities shape the experience in Bay Pines year-round.

  • How is the weather in Bay Pines?

    Bay Pines has mild winters with temperatures around 53–74°F (12–23°C) and hot, humid summers near 88–91°F (31–33°C). Rainfall increases in summer, especially from June through September, so lightweight clothing and a rain jacket are often recommended.

  • When is the best time to visit Bay Pines?

    Late fall through spring is often recommended for visiting Bay Pines, as temperatures are milder and humidity is lower. These months typically make outdoor activities and waterfront explorations more comfortable.

  • What are the best places to visit in Bay Pines?

    The area is known for its waterfront parks, marina access, and peaceful neighborhoods. The Bay Pines National Cemetery is often visited for its historic significance and quiet reflection spaces.

  • What are some hiking trails in Bay Pines?

    Bay Pines has access to nature trails in nearby preserves, where you can explore coastal habitats and spot local wildlife. Walking paths in waterfront parks are often recommended for a relaxed outdoor experience.

  • What are some family activities we can do in Bay Pines?

    Families often explore local parks, visit waterfront areas for picnics or fishing, and take part in kayak outings. Interactive museums and animal encounters can also be found in the surrounding region.

  • What are some of the best day trip ideas from Bay Pines?

    Popular day trip ideas from Bay Pines include exploring barrier island beaches, visiting art centers, or discovering nature preserves. Urban destinations nearby also have vibrant markets and historic neighborhoods to explore.

  • Are there any pet friendly accommodations available in Bay Pines?

    Bay Pines has a variety of pet-friendly accommodations, including vacation rentals with spacious yards and welcoming policies. Many hosts provide amenities for pets, making it easier to travel with your animal companions.

  • What are some local tips for visiting Bay Pines?

    Locals suggest wearing sun protection, especially during warmer months, and exploring water activities such as kayaking or fishing. Early mornings and evenings are often the most comfortable times for outdoor adventures in Bay Pines.

  • What is Bay Pines known for?

    Bay Pines is recognized for its connection to waterfront recreation, quiet residential neighborhoods, and the Bay Pines National Cemetery, a site of military and community remembrance. Outdoor activities and local fishing traditions are part of daily life.

  • What are the best hidden gems to explore in Bay Pines?

    You can explore locally rooted seafood shacks or tucked-away fishing spots frequently suggested by residents. Small art galleries and walking trails through natural preserves offer quieter ways to experience the community.

  • What are the best foods to try in Bay Pines?

    Seafood is frequently suggested in Bay Pines, where dishes like grouper sandwiches, shrimp, and fresh oysters reflect local tastes. You will also find a range of American comfort foods, Latin-inspired dishes, and southern barbecue in nearby eateries.

  • What should I bring for a trip to Bay Pines?

    Pack lightweight clothing, sun protection, and a hat for warmer seasons. A rain jacket or umbrella, comfortable shoes for outdoor walks, and a refillable water bottle are also useful during your stay.

  • What is the nightlife in Bay Pines like?

    Nightlife in Bay Pines is laid-back, with casual bars, waterfront lounges, and local restaurants hosting live music or trivia nights. For more energetic venues, consider exploring nearby neighborhoods known for their nightlife scenes.

  • What are the most popular events or festivals in Bay Pines?

    Local events in Bay Pines often include community gatherings at parks, arts and craft fairs, and seasonal celebrations tied to holiday weekends. The nearby region frequently hosts seafood festivals and outdoor concerts throughout the year.

  • Are there family friendly vacation rentals in Bay Pines?

    Bay Pines has many family-friendly vacation rentals, including homes with multiple bedrooms, spacious living areas, and amenities like full kitchens or access to pools. Some even include outdoor spaces for children to play.

Quick stats about holiday rentals in Bay Pines

  • Total holiday rentals

    Explore 220 holiday rentals in Bay Pines

  • Nightly prices starting at

    Bay Pines holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 11,220 verified reviews to help you choose

  • Family-friendly holiday rentals

    170 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    220 of Bay Pines holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bay Pines rentals

  • 4.8 Average rating

    Bay Pines stays are highly rated by guests – averaging 4.8 out of 5!

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Bay Pines