14 Best Places to Visit in Florida in May for Warm Water, Open Beaches, and Early Summer Ease

May marks the quiet shift toward summer in Florida. The water has fully warmed, daylight stretches long into the evening, and many destinations regain a sense of openness after spring crowds disperse. While temperatures rise, humidity hasn’t fully settled in yet, creating a window where beach days, boating, and outdoor dining still feel comfortable rather than demanding.

This guide explores the best places to visit in Florida in May, focusing on destinations that benefit from early-summer conditions without peak-season congestion. These are places where May delivers calmer beaches, better availability, and outdoor experiences that feel relaxed and intentional before summer travel accelerates.

1. Anna Maria Island

May is when Anna Maria Island leans fully into its easygoing coastal rhythm. The Gulf is warm and calm, ideal for swimming and paddleboarding, while the island itself feels noticeably quieter after spring break season. Afternoons are best spent on the beach, while mornings and evenings remain comfortable for biking and long shoreline walks.

The island’s residential feel shines in May, with fewer visitors competing for beach access or restaurant reservations. It’s a month that rewards travelers who value simplicity and unstructured days by the water.

Things to do in Anna Maria Island in May

• Swim in warm Gulf water during calm afternoons.

• Bike between Holmes Beach and Anna Maria City in the morning.

• Walk Bean Point in the evening for quieter sunsets.

• Enjoy outdoor dining without spring wait times.

Travel tips for visiting Anna Maria Island in May

• Midday sun is stronger by late May.

• Morning activities are most comfortable.

• Parking is easier than in peak summer.

Wander travel expert on why May feels effortless on Anna Maria Island

“I’ve visited Anna Maria Island across seasons, and May consistently feels the most natural. The water is warm enough to stay in for hours, crowds thin out, and you can structure your days around light and tides instead of reservations and traffic.”

Where to stay near Anna Maria Island in May

• Wander Serendipity Cloud – This beautifully designed retreat blends style and comfort for a serene coastal getaway. Cook gourmet meals in the Chef’s Kitchen or fire up the gas grill by the pool..

• Serendipity Waves – A renovated coastal retreat on Anna Maria Island, offering water views, direct beach access, and a stylish, light-filled interior.

• Wander Serendipity Haven – A luxury beachfront retreat on Anna Maria Island's North End, offering Gulf views, seamless indoor-outdoor living, and upscale features like a chef’s kitchen, outdoor pool, hot tub, and covered porch.

2. Cape Coral

Cape Coral’s canal network comes into its own in May. Warmer water temperatures and calmer mornings make boating and kayaking especially appealing, while the town itself feels quieter before summer family travel begins. Days are long, allowing for extended time on the water without rushing.

May also brings consistent weather, making it easier to plan multi-day boating or paddle routines. It’s an ideal destination for travelers who want space, water access, and a steady pace.

Things to do in Cape Coral in May

• Boat through canals during calm morning hours.

• Kayak before afternoon breezes build.

• Enjoy waterfront dining at sunset.

• Walk neighborhood paths in the evening.

Travel tips for visiting Cape Coral in May

• Early mornings offer the calmest water.

• Afternoon heat builds gradually.

• Sun protection becomes essential.

Wander travel expert on Cape Coral’s May advantage

“In May, Cape Coral feels built for the water. I’ve found the mornings are glassy, the canals are quiet, and you can settle into a routine that revolves entirely around being outside before summer crowds arrive.”

3. Fort Lauderdale

May softens Fort Lauderdale’s pace without dimming its energy. Beaches stay warm and swimmable, but visitor numbers drop after spring, making shoreline access easier. The Intracoastal Waterway remains a focal point, with excellent conditions for paddleboarding and cruising.

Outdoor dining thrives this month, especially in the evenings when breezes move through the city. May suits travelers who want an active coastal city without peak-season pressure.

Things to do in Fort Lauderdale in May

• Paddle the Intracoastal during calm mornings.

• Walk Fort Lauderdale Beach in the evening.

• Dine outdoors along Las Olas Boulevard.

• Take a late-day water taxi ride.

Travel tips for visiting Fort Lauderdale in May

• Humidity increases later in the month.

• Mornings are best for physical activity.

• Evenings remain comfortable near the water.

Wander travel expert on timing Fort Lauderdale in May

“I’ve spent time here in both spring and summer, and May is the sweet spot. The beaches open up again, the water stays perfect, and you can enjoy the city’s outdoor lifestyle without fighting crowds or extreme heat.”

Where to stay near Fort Lauderdale in May

• Wander Fort Lauderdale Harbor – The home boasts an open layout with a brand-new kitchen, alfresco dining, a pool, a jacuzzi, and a gas BBQ for outdoor gatherings.

• Wander Fort Lauderdale Oceanfront – An award-finalist luxury beachfront retreat offering direct access to golden sands. This exquisite property boasts a private ocean-view infinity pool, a corner hot tub, and a sun-drenched patio with a BBQ area for elegant al fresco dining.

4. Gulf Breeze

Gulf Breeze benefits from May’s early-summer calm. The soundside waters warm quickly, creating ideal conditions for paddling and swimming, while Gulf Islands National Seashore feels wide open before summer tourism peaks.

Temperatures are warm but manageable, making May well suited for beach days paired with light exploration. The area’s slower rhythm matches the month perfectly.

Things to do in Gulf Breeze in May

• Paddle calm soundside waters in the morning.

• Walk the Gulf Islands National Seashore comfortably.

• Relax on quieter beaches midweek.

• Watch sunsets over the sound.

Travel tips for visiting Gulf Breeze in May

• Soundside water warms faster than the Gulf.

• Afternoon breezes bring relief from heat.

• Weekdays are especially quiet.

Wander travel expert on Gulf Breeze before summer crowds

“In May, Gulf Breeze still feels untouched. I’ve found it’s the last month where you can enjoy long beach days and empty shorelines before summer traffic really arrives.”

Where to stay near Gulf Breeze in May

• Wander Pensacola Beach – Wake up to the soothing sounds of the waves and step onto the pristine sands just steps from your door. Spend your days swimming in the refreshing outdoor pool or challenging your companions to a game of pool on the conveniently located pool table.

5. Islamorada

May is a standout month in Islamorada for water clarity and warmth. Winds tend to be lighter early in the month, creating excellent conditions for snorkeling, boating, and backcountry exploration. The Keys feel calmer once spring visitors depart.

Long daylight hours support full days on the water, while evenings remain breezy enough for outdoor dining. May suits travelers who want the Keys experience without summer intensity.

Things to do in Islamorada in May

• Snorkel reefs during clear morning conditions.

• Kayak mangroves before midday heat.

• Enjoy sunset dinners along the water.

• Spend full days boating offshore.

Travel tips for visiting Islamorada in May

• Early mornings offer the best water conditions.

• Humidity rises toward late May.

• Light rain showers are brief.

Wander travel expert on Islamorada’s May water conditions

“I’ve logged a lot of time on the water here, and May consistently delivers. The water is warm, visibility is strong, and the islands feel less crowded, which makes boating and snorkeling far more enjoyable.”

Where to stay near Islamorada in May

• Wander Islamorada Beach – This elegant home features three spacious living rooms, a social room, a beachfront terrace, and a stunning third-story oceanfront terrace, perfect for taking in the panoramic views.

• Wander Islamorada Island – This gated Caribbean-style retreat spans over 15 acres of lush tropical landscape surrounded by the mesmerizing blue-green waters of the Atlantic Ocean. Featuring modern utilities, a sparkling pool, private dockage, a tennis court, and a pool house, Wander Islamorada Island offers an unparalleled luxury experience.

• Wander Islamorada Retreat – Outside, guests can enjoy a stunning heated waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats.

6. Marco Island

Marco Island in May offers warm Gulf water and noticeably quieter beaches. Spring crowds have moved on, yet summer vacationers haven’t arrived, creating a rare sense of openness along the shoreline.

May is also an excellent month for exploring the Ten Thousand Islands, as heat remains manageable earlier in the day and wildlife activity stays visible.

Things to do in Marco Island in May

• Swim at Tigertail Beach during calm afternoons.

• Boat through Ten Thousand Islands in the morning.

• Walk the beach in the evening.

• Enjoy waterfront dining at sunset.

Travel tips for visiting Marco Island in May

• Mornings are best for outdoor exploration.

• Afternoons warm quickly.

• Water temperatures are ideal.

Wander travel expert on Marco Island’s May quiet

“Marco Island in May feels expansive. I’ve found the beaches are wide open, the water is perfect, and you can explore the islands without feeling rushed by heat or crowds.”

• Wander Marco Island Waterfront – A luxurious coastal retreat designed for both relaxation and recreation. Nestled along a tranquil canal, this home features a private boat dock, outdoor pool, kayaks, and breathtaking water views. Inside, you’ll find entertainment options like a pool table, game console, and smart TVs throughout.

• Wander Marco Lagoon – A luxurious waterfront retreat offering an unparalleled escape on Marco Island. Spend your days lounging by the sparkling outdoor pool or unwinding in the soothing hot tub, both perfectly positioned to maximize the stunning vista.

• Wander Marco Island Villa – lounging by the sparkling outdoor pool and later relaxing in the soothing hot tub. The private boat dock provides direct access to the shimmering waters, perfect for exploring the coastline or simply enjoying the serene surroundings.

→ Explore our other luxury vacation rentals in Marco Island

7. Naples

May gives Naples a calmer, more residential feel. The Gulf stays warm and flat, ideal for swimming and paddleboarding, while the city itself slows after peak season. Fifth Avenue remains active but easier to navigate.

Evenings are particularly enjoyable in May, with outdoor dining still comfortable before summer humidity builds fully.

Things to do in Naples in May

• Swim during warm, calm Gulf afternoons.

• Paddle Clam Pass early in the day.

• Walk Fifth Avenue in the evening.

• Watch the sunset from the Naples Pier.

Travel tips for visiting Naples in May

• Early mornings are best for activity.

• Afternoon heat increases later in the month.

• Restaurant availability improves after spring.

Wander travel expert on Naples before summer settles in

“I’ve always preferred Naples in May. The city exhales after spring, the water is inviting, and you can enjoy the beaches without the structured pace that defines peak season.”

Where to stay near Naples in May

• Wander Naples Ranch – This 3-bedroom property with lake access and forest views has a full indoor game room with a pool table, ping pong, foosball, and console gaming. Outside, the enclosed heated pool and spa invite you to unwind.

8. Palm Coast

Palm Coast becomes increasingly appealing in May as Atlantic waters warm and crowds thin. The area’s trails, beaches, and Intracoastal waterways support a relaxed outdoor routine, especially earlier in the day.

May suits travelers who enjoy nature-focused days paired with quiet evenings. The slower pace feels intentional rather than seasonal.

Things to do in Palm Coast in May

• Kayak the Intracoastal in the morning.

• Walk Atlantic beaches before midday heat.

• Explore Washington Oaks Gardens.

• Relax outdoors in the evening.

Travel tips for visiting Palm Coast in May

• Morning hours are most comfortable.

• The afternoon sun is strong.

• Bugs increase near waterways.

Wander travel expert on Palm Coast’s May appeal

“I’ve spent time here in different seasons, and May stands out for how calm it feels. You get warm water, open beaches, and enough quiet to actually enjoy the natural surroundings.”

Where to stay near Palm Coast in May

• Wander Palm Coast Dunes – An open floor plan flows to a secluded patio with pool, sun shelf, grill, and wet bar, while upstairs an entertainment lounge opens to a breezy balcony.

• Wander Palm Coast Sea – Perched directly on Cinnamon Beach, this home offers breathtaking ocean views from expansive balconies, a private pool, and seamless beach access.

• Wander Palm Coast Waterfront – A brand-new luxury retreat just a 5-minute walk to the beach, offering elegant coastal living with panoramic lagoon views. Designed for both relaxation and entertainment, this spacious home features two master suites, a chef’s kitchen with a quartz island and 48” gas stovetop.

→ Explore our other luxury vacation rentals in Palm Coast

9. Port St. Joe

May is one of the last months Port St. Joe feels completely unhurried. Gulf waters warm quickly, fishing improves, and beaches remain largely empty. The town’s quiet personality aligns well with May’s slower travel period.

It’s an ideal time for travelers seeking solitude, scenery, and long days outdoors.

Things to do in Port St. Joe in May

• Walk St. Joseph Peninsula State Park.

• Fish along the bay during early mornings.

• Kayak calm coastal waters.

• Watch the sunset along the shoreline.

Travel tips for visiting Port St. Joe in May

• Mornings offer cooler temperatures.

• Limited services require advance planning.

• Evenings cool slightly.

Wander travel expert on catching Port St. Joe at the right moment

“I’ve found May is the month to be here. The water is warm, the beaches are empty, and the town still feels untouched before summer traffic reaches the Forgotten Coast.”

Where to stay near Port St. Joe in May

• Wander Secluded Dunes – This secluded retreat perfectly balances relaxation and fun in a stunning oceanfront setting. Inside, a vibrant game room features pool and ping pong tables for entertainment, while a cozy gas fireplace adds warmth to evenings.

• Wander Cape San Blas – Whether you’re enjoying the sunset by the water, gathering for games, or watching the waves roll in, this home is designed for both comfort and connection.

10. Sarasota

Sarasota in May balances cultural energy with coastal calm. Beaches like Siesta Key remain inviting, while the city’s arts and dining scenes slow slightly after spring events wrap up.

May’s longer days allow visitors to combine beach time with museums, gardens, and waterfront walks without feeling rushed.

Things to do in Sarasota in May

• Swim at Siesta Key during warm afternoons.

• Visit Marie Selby Botanical Gardens.

• Walk the bayfront in the evening.

• Dine outdoors comfortably.

Travel tips for visiting Sarasota in May

• Humidity builds later in the month.

• Morning beach visits are best.

• Parking is easier than in spring.

Wander travel expert on Sarasota’s May balance

“I’ve experienced Sarasota in peak season, and May feels refreshingly calm. You still get everything the city offers, but with more space and fewer crowds shaping your day.”

Where to stay near Sarasota in May

• Wander Sarasota Paradise – The perfect place for 6 guests to indulge in the ultimate relaxation with a private indoor pool and enjoy the on-site mini golf course.

• Wander Sarasota Retreat – A coastal escape for those seeking entertainment, the well-appointed game room provides endless hours of fun, while the private balcony offers a tranquil retreat to enjoy breathtaking views.

• Wander Sarasota Springs – This stunning property boasts a refreshing outdoor pool, perfect for cooling off under the Florida sun, and a spacious patio ideal for al fresco dining.

11. Saint George Island

Saint George Island remains peaceful in May, with warm Gulf water and minimal crowds. The island’s natural beauty takes center stage as beach days stretch longer and fishing conditions improve.

May is ideal for travelers who value simplicity and time spent outdoors.

Things to do in Saint George Island in May

• Walk the beach during early mornings.

• Fish along the shoreline.

• Explore state park trails.

• Watch the sunset from quiet stretches of sand.

Travel tips for visiting Saint George Island in May

• Limited dining options require planning.

• Heat builds midday.

• Mornings and evenings are best.

Wander travel expert on Saint George Island’s early-summer calm

“I’ve visited Saint George Island before summer sets in, and May is exceptional. The island feels wide open, the water is warm, and you can enjoy its natural pace without interruption.”

Where to stay near Saint George Island in May

• Wander St. George Island – Wander St. George Island is an oceanfront beach home with a private boardwalk out to the sparkling sands.

12. Tampa

May signals Tampa’s shift toward summer without full intensity. The Riverwalk, Bayshore Boulevard, and waterfront parks remain comfortable earlier in the day, while evenings are ideal for dining and strolling.

It’s a strong month for travelers who want city energy balanced with outdoor access.

Things to do in Tampa in May

• Walk the Riverwalk in the morning.

• Bike Bayshore Boulevard.

• Dine outdoors in Hyde Park.

• Enjoy the sunset along the bay.

Travel tips for visiting Tampa in May

• Mornings are best for activity.

• Afternoon heat increases late May.

• Evenings remain pleasant.

Wander travel expert on Tampa before peak heat

“I’ve found May is when Tampa still feels approachable outdoors. You can explore the city, enjoy the waterfront, and avoid the full force of summer heat.”

Where to stay near Tampa in fall

• Wander Tampa Bay – This award-winning estate offers a private, resort-style escape featuring a pool, a refreshing plunge pool, golf putting green, and an outdoor shower.

13. Vero Beach

Vero Beach in May feels unhurried and warm. Atlantic waters are ideal for swimming, and the town’s quiet character becomes more pronounced after spring travelers leave.

It’s a month suited to travelers who enjoy beach routines and peaceful evenings.

Things to do in Vero Beach in May

• Swim during warm afternoon hours.

• Walk South Beach Park in the morning.

• Visit botanical gardens.

• Enjoy relaxed waterfront dining.

Travel tips for visiting Vero Beach in May

• Ocean conditions vary with wind.

• Mornings are cooler.

• Evenings stay warm.

Wander travel expert on May’s understated charm

“I’ve always appreciated Vero Beach in shoulder seasons, and May delivers warm water and quiet beaches without the rush that comes later.”

Where to stay near Vero Beach in May

• Wander Vero Beach – With direct beach access just steps away, the experience is both effortless and extraordinary. This vacation rental also honors sea turtle and dune protection regulations, as outlined by Indian River County, ensuring a stay that’s as respectful as it is luxurious.

14. West Palm Beach

May brings warmth and breathing room to West Palm Beach. Beaches remain inviting, while downtown areas feel less congested after spring events end.

Outdoor markets, waterfront paths, and dining thrive in early summer conditions.

Things to do in West Palm Beach in May

• Walk the Lake Trail early in the day.

• Relax at Municipal Beach.

• Explore downtown in the evening.

• Dine outdoors comfortably.

Travel tips for visiting West Palm Beach in May

• The midday sun is strong.

• Afternoons are best near the water.

• Evenings remain breezy.

Wander travel expert on West Palm Beach’s May rhythm

“In May, West Palm Beach slows just enough. I’ve found the beaches open up, the weather stays reliable, and you can enjoy the city without planning every move.”

Where to stay near West Palm Beach in May

• Wander West Palm Beach – This stylish retreat boasts a 2,000 sq ft rooftop terrace, outdoor pool, jacuzzi, a steam room, and modern master suite with bathtub. 

• Wander Palm Beach Horizon – This serene retreat blends contemporary elegance with smart home features, high-end designer furnishings, and a fully equipped chef’s kitchen.

Plan your May escape with luxury vacation rentals in Florida

May rewards travelers who arrive just ahead of peak summer. The best places to visit in Florida in May offer warm water, open beaches, and long days shaped by ease rather than schedules. Choosing the right destination, and looking at the right luxury vacation rentals in Florida sets the tone for a stay that feels relaxed, spacious, and perfectly timed.