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Island Grand at TradeWinds

4.0 star property
Travelers find the perfect balance of adventure and relaxation at this beachfront resort with five outdoor pools and plenty of water activities

Choose dates to view prices

Island Grand at TradeWinds on Upham Beach offers beach/poolside bars, two restaurants, volleyball, ecotours, kayaking, five outdoor pools, a waterslide, and a kids' club. Perfect for families seeking excitement and relaxation.

Reviews

7.8 out of 10
Good

Popular amenities

  • Hot tub
  • Spa
  • Pet friendly
  • Free WiFi

Room options

Available filters for rooms
Showing 9 of 9 rooms

View all photos for Villa, 2 Double Beds, Balcony (Gulf Front View)

Villa, 2 Double Beds, Balcony (Gulf Front View) | Pillowtop beds, in-room safe, desk, laptop workspace

Villa, 2 Double Beds, Balcony (Gulf Front View)

  • Ocean view
  • 300 sq ft
  • 1 bedroom
  • Sleeps 5
  • 2 Double Beds
  • Free WiFi

View all photos for Room, 2 Queen Beds, Balcony (Tropical View)

A hotel room with two beds, a TV, a dresser, and a balcony with a city view.

Room, 2 Queen Beds, Balcony (Tropical View)

8.0 out of 10
Very good
(28 reviews)
  • Resort view
  • 300 sq ft
  • 1 bedroom
  • Sleeps 5
  • 2 Queen Beds
  • Free WiFi

View all photos for Villa, Multiple Beds, Balcony (Tropical View, 2 Queen & 2 Double)

A hotel room with a dining table, chairs, a sofa, and a balcony with a view.

Villa, Multiple Beds, Balcony (Tropical View, 2 Queen & 2 Double)

7.2 out of 10
Good
(7 reviews)
  • Resort view
  • 820 sq ft
  • 1 bedroom
  • Sleeps 9
  • 4 Queen Beds
  • Free WiFi

View all photos for Villa, 2 Double Beds, Balcony (Tropical View)

A hotel room with a large window offering a city view, a sofa with patterned cushions, a dining table with chairs, and a blue textured rug.

Villa, 2 Double Beds, Balcony (Tropical View)

7.2 out of 10
Good
(9 reviews)
  • Resort view
  • 426 sq ft
  • 1 bedroom
  • Sleeps 5
  • 2 Double Beds
  • Free WiFi

View all photos for Deluxe Room, 2 Double Beds

A hotel room with two beds, a desk, a chair, a dresser, and a mirror.

Deluxe Room, 2 Double Beds

7.6 out of 10
Good
(69 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 5
  • 2 Double Beds
  • Free WiFi

View all photos for Studio Suite, 2 Double Beds (Courtyard)

A living room with a sofa, a dining table with chairs, a lamp, and a TV mounted on the wall.

Studio Suite, 2 Double Beds (Courtyard)

  • 384 sq ft
  • 1 bedroom
  • Sleeps 5
  • 2 Double Beds
  • Free WiFi

View all photos for Room, 1 King Bed, Balcony (Tropical View)

A hotel room with a large bed, a balcony with a view, a seating area, and a desk.

Room, 1 King Bed, Balcony (Tropical View)

7.2 out of 10
Good
(21 reviews)
  • Resort view
  • 300 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 1 King Bed

A hotel room with a large bed, a desk, a chair, a TV, and a bathroom visible through an open door.

Deluxe Room, 1 King Bed

8.6 out of 10
Excellent
(14 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed
  • Free WiFi

View all photos for Room, 2 Queen Beds, Balcony (Gulf Front View)

A hotel room with two beds, a balcony with a view of the ocean, and a seating area with a table and chairs.

Room, 2 Queen Beds, Balcony (Gulf Front View)

7.0 out of 10
Good
(14 reviews)
  • Ocean view
  • 300 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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About the neighborhood

Located in St. Pete Beach, Island Grand at TradeWinds is on the beach. Travelers eager for a bit of culture can stop by Salvador Dali Museum, while those wishing to experience the area's natural beauty can explore St. Petersburg - Clearwater Beaches and Pass-a-Grille Beach. Dolphin Landings Charter Boat Center and Upham Beach are two other places to visit that come recommended. Looking to get your feet wet? Scuba diving and fishing adventures can be found near the property. Visit our St. Pete Beach travel guide
View more Resorts in St. Petersburg - Clearwater
Map
5500 Gulf Blvd, St. Pete Beach, FL, 33706

What's nearby

  • A pink hotel with a beach and ocean in the background.
    St. Petersburg - Clearwater Beaches
    1 min walk - 0.0 miles
  • A water park with a large pool, slides, and inflatable rings.
    Splash Island Water Park
    2 min walk - 0.1 miles
  • A dock with boats and a sign that reads "Boat Rides Dolphin Landings".
    Dolphin Landings Charter Boat Center
    13 min walk - 0.7 miles
  • An aerial view of a coastal resort with a beach, water, and a hotel.
    Pass-a-Grille Beach
    14 min walk - 0.8 miles
  • A wooden boardwalk with benches, surrounded by tall grass and palm trees, leading to a beach with buildings in the background.
    Upham Beach Park
    17 min walk - 0.9 miles

Getting around

  • St. Petersburg, FL (SPG-Albert Whitted)
    17 min drive

Restaurants

  • Coconut Charlie’s Beach Bar & Grill
    8 min walk
  • TradeWinds Lobby & Bar
    1 min walk
  • Crabby Bill's Seafood
    7 min walk
  • Jimmy B's Beach Bar
    9 min walk
  • Dunkin'
    6 min walk

About this property

Island Grand at TradeWinds

  • Upscale family-friendly resort near Upham Beach
  • Located close to Dolphin Landings Charter Boat Center, Island Grand at TradeWinds provides 2 poolside bars, a beach bar, and a grocery/convenience store. This resort is a great place to bask in the sun with a beachfront location, beachfront dining, and sun loungers. Treat yourself to a massage or other spa services. At the 4 on-site restaurants, enjoy breakfast, lunch, dinner, and Mexican cuisine. The 24-hour gym offers yoga classes and fitness classes; other things to do include volleyball, ecotours, and kayaking. In addition to a terrace and shopping on site, guests can connect to free in-room WiFi.
  • Other perks include:
    • 5 outdoor pools and a children's pool, along with a waterslide and sun loungers
    • Self parking (surcharge), a roundtrip airport shuttle (surcharge), and express check-out
    • A water park (surcharge), a children's club (surcharge), and 2 outdoor pickleball courts
    • Wedding services, ATM/banking services, and a paddleboard on site
    • Guest reviews speak highly of the family-friendly amenities, beach locale, and helpful staff
  • Room features
  • All 381 rooms boast comforts such as laptop-friendly workspaces and air conditioning, as well as thoughtful touches like free WiFi and desk chairs. Guest reviews speak positively of the clean rooms at the property.
  • Other conveniences in all rooms include:
    • Pillowtop mattresses, rollaway/extra beds (surcharge), and cribs/infant beds (surcharge)
    • Bathrooms with designer toiletries and shower/tub combinations
    • HDTVs with premium channels
    • Refrigerators, microwaves, and cookware/dishes/utensils

Similar properties

Property grounds
RumFish Beach at TradeWinds
St. Pete Beach
  • Pool
  • Hot tub
  • Spa
  • Pet friendly
8.2 out of 10, Very Good, 2,180 reviews
$225 nightly
The price is $254
Jul 27 - Jul 28
Total with taxes and fees
RumFish Beach at TradeWinds
Compare similar properties

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Roundtrip airport shuttle (surcharge)
  • Self parking on site (USD 25 per night; includes in/out privileges)
  • Limited onsite self parking
  • Wheelchair-accessible parking available

Food and drink

  • 2 coffee shops/cafes
  • 2 poolside bars
  • 4 bars/lounges
  • 4 restaurants
  • A beach bar
  • Snack bar/deli

Restaurants on site

  • Coastal Pizza
  • Palm Court Italian
  • Pete's Gulf Bistro
  • Playa Taco
  • Salty's Beach Lounge

Things to do

  • 2 hot tubs
  • 2 outdoor pickleball courts
  • 24-hour gym
  • 5 outdoor pools
  • Arcade/game room
  • Beach volleyball
  • Beach yoga
  • Boat tours
  • Children's club
  • Children's pool
  • Ecotours
  • Fitness classes
  • Kayaking
  • Mini golf
  • Outdoor pool (guest access)
  • Paddleboard
  • Parasailing
  • Personal motorized watercraft
  • Shopping
  • Snorkeling
  • TV in common areas
  • Water park
  • Water sports equipment
  • Waterslide

Family friendly

  • 5 outdoor pools
  • Arcade/game room
  • Children's club (surcharge)
  • Children's pool
  • Crib (surcharge)
  • Grocery/convenience store
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Mini golf
  • Rollaway/extra bed (surcharge)
  • Snack bar/deli
  • Water park (surcharge)
  • Waterslide

Conveniences

  • 24-hour front desk
  • ATM
  • Gift shop/newsstand
  • Grocery/convenience store
  • Laundry facilities

Guest services

  • Dry cleaning/laundry service
  • Housekeeping (daily)
  • Multilingual staff
  • Porter/bellhop
  • Tour and ticket assistance
  • Wedding services

Business services

  • Conference center
  • Meeting rooms

Outdoors

  • Beach loungers
  • Beach towels
  • Beach umbrellas
  • On the beach
  • Pool loungers
  • Terrace

Spa

  • Massage
  • Spa services

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Braille/raised signage
  • Elevator
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible lounge
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible registration desk

More

  • 7 floors
  • Ballroom
  • Banquet hall
  • Designated smoking areas
  • Reception hall

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Crib (surcharge)
  • Pillowtop mattress
  • Rollaway/extra bed (surcharge)

Bathroom

  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shower/bathtub combination
  • Towels provided

Entertainment

  • Flat-screen TV with premium cable channels

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Refrigerator

More

  • Access via exterior corridors
  • Air conditioning (climate-controlled)
  • Connecting rooms available
  • Desk
  • Desk chair
  • Iron/ironing board
  • Laptop workspace
  • Phone
  • Safe

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: midnight
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM
Contactless check-out available
Express check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 75 per accommodation, per night
Service animals are welcome, and are exempt from fees
Welcoming dogs only

Children and extra beds

Children are welcome
2 children, up to the age of 17 years, can stay for free if using existing beds when occupying the parent or guardian's room
Rollaway/extra beds are available for USD 25.0 per night
Cribs (infant beds) are available for USD 25.0 per night

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 62.15 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • Beach access
  • Beach loungers
  • Beach towels
  • Business center/computer access
  • Concierge service
  • Fitness center access
  • Fitness/yoga classes
  • In-room coffee
  • In-room safe
  • Partner property access
  • Partner property pool access
  • Pool access
  • Sporting facilities or equipment

We have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 25.00 per night (in/out privileges)
  • Pet fee: USD 75 per accommodation, per night
  • Service animals are exempt from fees
  • Crib (infant bed) fee: USD 25.0 per night
  • Rollaway bed fee: USD 25.0 per night

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a smoke detector
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

We should mention

Reservations are required for massage services; reservations can be made by contacting the property prior to arrival, using the contact information on the booking confirmation
The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation

Frequently asked questions

Does Island Grand at TradeWinds have a pool?

Yes, this property has 5 outdoor pools and a children's pool.

How much does it cost to stay at Island Grand at TradeWinds?

As of Jul 22, 2026, prices found for a 1-night stay for 2 adults at Island Grand at TradeWinds on Jul 27, 2026 start from $287, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Island Grand at TradeWinds pet-friendly?

Yes, dogs are allowed at this property. There's a fee of USD 75 per accommodation, per night. Service animals are exempt from fees.

How much is parking?

Self parking is available for USD 25.00 per night. Limited spots are available.

What time is check-in at Island Grand at TradeWinds?

Check-in start time: 4:00 PM; Check-in end time: midnight.

What time is check-out at Island Grand at TradeWinds?

Check-out is at 11:00 AM.

Does Island Grand at TradeWinds provide a shuttle to the airport?

Yes, there's an airport shuttle.

Where is Island Grand at TradeWinds located?

Nestled on the beach, this St. Pete Beach resort is within a 15-minute walk of Upham Beach and Dolphin Landings Charter Boat Center. John's Pass Village & Boardwalk and Salvador Dali Museum are also within 12 mi (20 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Island Grand at TradeWinds Reviews

7.8

Good

7.8

Cleanliness

8.0

Amenities

8.2

Staff & service

7.2

Property conditions & facilities
Rating 10 - Excellent. 556 out of 1273 reviews
Rating 8 - Good. 269 out of 1273 reviews
Rating 6 - Okay. 220 out of 1273 reviews
Rating 4 - Poor. 118 out of 1273 reviews
Rating 2 - Terrible. 110 out of 1273 reviews

Reviews

Verified

10/10 Excellent

Ariel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very family friendly. Everyone one is super accommodating and helpful Would definitely stay here again
Stayed 3 nights in Jul 2026
Verified

6/10 Okay

Ariana

Liked: Amenities
Overall is a good resort,a lot of amenities and friendly staff. The food at the restaurants is delicious. The cons are that near the elevators smells bad, and the entrance from the bedrooms and elevators are dirty.
Stayed 5 nights in Jul 2026
Verified

10/10 Excellent

John T

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was our second visit to tradewinds grand Island resort. We visited when our children were younger six years ago and returned recently. Both times we were impressed with the amenities, convenient location, beautiful beach, views, and family, friendly activities.
Stayed 2 nights in Jul 2026
Verified

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful trip, had a bunch of included amenities and an overall amazing value. Will go back!
Stayed 3 nights in Jun 2026
Verified

10/10 Excellent

Jeff

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff and location are great. Poolside bar and restaurant is amazing. Close to restaurants, shopping, and pier 60.
Stayed 3 nights in Jun 2026
Verified

10/10 Excellent

Maria

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We come here all the time best food best entertainment best service
Stayed 3 nights in Jun 2026
Verified

6/10 Okay

Sushila

Liked: Staff & service
Beach was beautiful and staff there were very kind and helpful and its very family friendly
Stayed 3 nights in May 2026
Verified

10/10 Excellent

Adrian

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was clean, the staff was helpful and friendly, and the food service was excellent.
Stayed 3 nights in May 2026
Verified

10/10 Excellent

Kayla

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The beach was beautiful, the rooms were clean and did not smell musty, and the kids had a wonderful time with all the amenities!
Stayed 3 nights in May 2026
Verified

8/10 Good

Marcos

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The beach was pretty good. The rooms were clean.
Stayed 2 nights in May 2026
Verified

10/10 Excellent

Carl

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a great week long vacation at the Island Grand/Tradewinds. Staff very professional, excellent house keeping daily, resort amenities were great, beach attendants friendly and helpful. Overall an excellent resort and will come back again. Beach and gulf water was delightful!
Stayed 7 nights in May 2026
Verified

10/10 Excellent

Stephen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
What a wonderful experience at your resort. Great helpful staff, room was great with an even better view of the gulf. Great activities for kids from slides to crafts and pool movie, reptile class, jewelry making♥️‼️Highly recommended
Stayed 6 nights in Mar 2026
Verified

8/10 Good

jeanette

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel was average, but the room was very beautiful, very comfortable and had everything I needed. Staff was incredibly nice ! Not much to do at the hotel, but being right next to the gulf and turquoise water made up for it!
Stayed 3 nights in May 2026
Verified

10/10 Excellent

Jarrod

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great if you have kids
Stayed 3 nights in May 2026
Verified

8/10 Good

Jillian

Liked: Cleanliness, staff & service
Family friendly
Stayed 4 nights in May 2026
Verified

10/10 Excellent

Angie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
So many activities for all ages and lits of restaurant options right on the property! Great stay!
Stayed 4 nights in Mar 2026
Verified

8/10 Good

Elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We love how family friendly the property is. We’ve gone five times and i feel like it gets better each time. It is alittle pricey but with the new restaurants we didn’t mind since the food was really good. The arcade is not great but other than that we love it!
Stayed 5 nights in May 2026
Verified

10/10 Excellent

Vanessa

Liked: Cleanliness, staff & service, amenities
Perfect location and plenty of activities for both adults and kids
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Gabrielle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I’ve been coming here since a kid. This place is very clean. The service is wonderful. Champagne toast upon arrival (included in resort fee) slide on beach, water fitness, stuff for kids like crafts and such, movies at night in the pool for the kids.. and little peddle boats that you can ride around resort. Not to mention free professional photo with their photographer on beach. (Have to call to set up, I recommend doing it ahead.. we didn’t get to get our photo) The pool side service with drinks and all is 🔥🔥 if in this area I recommend staying here. Been a fav since I was a kid.
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

Annie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
very close to beach and plenty to do
Stayed 4 nights in Feb 2026
Verified

8/10 Good

Vita

Liked: Cleanliness, amenities, property conditions & facilities
Amenities: Excellent. A lot of kids game/activity, pool, beach access. Perfect resort for family. Room: Clean. Very clean. Staff: pool staff were friendly n helpful. Salty's bartender (female) maybe can be little but nice since we also paid 20% tips for every drink we purchase. Other: I wish they told me in detail by email which type of balcony room that i was upgrading. Got room 2238 which balcony is only 45cm length and noise in the morning from staff's talking near laundry room or sth. Overall, the place was amazing.
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was great and friendly
Stayed 6 nights in Mar 2026
Verified

10/10 Excellent

Fatos

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place for a family vacation. Everything from check-in to check-out was great. Shpresa at the fron desk was absolutely wonderful and she made the stay pleasant and hassle free.
Stayed 4 nights in Apr 2026
Verified

8/10 Good

carolyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very friendly staff, amenities galore, always something going on and things to do with the kids. Only complaint would be the shower. When a hotel caters to families, a pull down showerhead would be so beneficial!! The littles had a hard time getting shampoo and conditioner out. And of course as a female, I much prefer a pulldown showerhead, sand gets everywhere!
Stayed 4 nights in Jun 2026
Verified

10/10 Excellent

Elizabeth Anne

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lots of activities for kids.
Stayed 4 nights in Apr 2026