Top Caribbean Self-guided Tours & Rentals

Q: What are the best options for Caribbean Self-guided Tours & Rentals?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Self-guided Tours & Rentals are: Beach and Ocean float rental Can Am Rental - YOU DRIVE! Inflatable Paddle Boards Bicycle Rental in Grand Turk Jetski Rental in Providenciales

Q: What are the best kid-friendly options for Caribbean Self-guided Tours & Rentals Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Self-guided Tours & Rentals are: 2 Hour Bike Rental Colonial Zone / Santo Domingo Rental Kayaking or Stand-up Paddle 2H Children's Treasure Hunt Walking Tour Bicycles rental in Old San Juan Clear Kayak Rental Grand Turk Island View all kid-friendly Tours →

Q: Which Caribbean Self-guided Tours & Rentals have Instant Confirmation?

Caribbean Self-guided Tours & Rentals with Instant Confirmation include: Fort-de-France: Caribbean City Puzzle Adventure 2 Hour Bike Rental Colonial Zone / Santo Domingo JET SKI, Skim Board,& Wave Board Rentals Cabarete, Sosua Harbour Lights - Beach Chair & Shared Umbrella Rental Kayaking or Stand-up Paddle 2H View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Self-guided Tours & Rentals have Hotel Pickup?

No problem. These Caribbean Self-guided Tours & Rentals include Hotel Pickup: 4WD Excursion to the Water Cave and Macao Beach Honda Mastering the Aquatic Cave and Macao Cars for Rent in Punta Cana 1 Hour Private Kayak Rental In Grand Turk Puerto Plata Cabarete Inflatable Paddle Board/ Kayak Rental View all Tours with Hotel Pickup →

Q: Got any more Caribbean trip ideas?

We sure do. Check out our curated lists of hand-picked Caribbean Tours. Top 10 Caribbean 2026 Senior-friendly tours Caribbean The best tours and activities for culture lovers in Caribbean Top Day Trips from Caribbean Things to do in Caribbean this summer View all Caribbean Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Caribbean?

Based on our sales data over the past year, the most popular styles of tours and activities in Caribbean are: Caribbean Luxury & Special Occasions Caribbean Luxury Tours Caribbean Tours & Sightseeing Caribbean Shore Excursions Caribbean Port Transfers View all tour styles in Caribbean →

Deep sea fishing in Punta Cana and Bávaro.

The best service and staff in the area! We are known for our knowledgeable and helpful staff who will accompany you throughout the tour. …More

Punta Cana, Dominican Republic

4.9 (30)

Deep sea fishing in Punta Cana and Bávaro.

The best service and staff in the area! We are known for our knowledgeable and helpful staff who will accompany you throughout the tour....

4 hours Free Cancellation

4.9 (30)

from
$520

Private Jeep Tour: Explore Aruba's National Park Off-Road

Your Jeep. Your Crew. Your Aruba Adventure. Experience Aruba your way with our customized 4x4 Private Jeep tours. Our friendly guide will pick you up …More

4.7 (21)

Private Jeep Tour: Explore Aruba's National Park Off-Road

Your Jeep. Your Crew. Your Aruba Adventure. Experience Aruba your way with our customized 4x4 Private Jeep tours. Our friendly guide will pick you up...

4 hours Hotel pickup offered Free Cancellation

4.7 (21)

from
$550

Island Life Jeep Tours - Your Day Your Way Private Excursion!

Experiencing St. Thomas with Island Life Jeep Tours means "Your Day, Your Way"! All destinations are customized with your driver the morning of your tour, …More

Cruz Bay, US Virgin Islands

5.0 (35)

Island Life Jeep Tours - Your Day Your Way Private Excursion!

Experiencing St. Thomas with Island Life Jeep Tours means "Your Day, Your Way"! All destinations are customized with your driver the morning of your tour,...

7 hours Hotel pickup offered Free Cancellation

5.0 (35)

from
$575

Bareboat Zodiac RIB Rentals in St John VI

Experience the natural beauty of St. John, US Virgin Islands with Wharfside Watersports' bareboat Zodiac rentals. Set forth from Cruz Bay and circumnavigate St. John …More

5.0 (159)

Bareboat Zodiac RIB Rentals in St John VI

Experience the natural beauty of St. John, US Virgin Islands with Wharfside Watersports' bareboat Zodiac rentals. Set forth from Cruz Bay and circumnavigate St. John...

4 to 8 hours Free Cancellation

5.0 (159)

from
$595

Sonic Charters - Half Day Boat Charter - 33' Jupiter

Sonic Charters is able to accommodate groups up to 9 passengers on our top of the line power boats. Our trips include: • One of our …More

5.0 (14)

Sonic Charters - Half Day Boat Charter - 33' Jupiter

Sonic Charters is able to accommodate groups up to 9 passengers on our top of the line power boats. Our trips include: • One of our...

8 hours Hotel pickup offered Free Cancellation

5.0 (14)

from
$769

All the guests of our Jet Ski rentals ride on the vessels that are in perfect technical and aesthetical condition. Most of our PWC’s have …More

Grand Cayman, Cayman Islands

5.0 (2)

6 Hour Jet Ski Rental Full Day

All the guests of our Jet Ski rentals ride on the vessels that are in perfect technical and aesthetical condition. Most of our PWC’s have...

6 hours Free Cancellation

5.0 (2)

from
$850

Be freedom on the boat for a beautiful day? With Tropical Boat, you can rent our boat WHITE SHARK 265 with 2 engines 150CV Yamaha …More

5.0 (4)

Rent White Shark 265

Be freedom on the boat for a beautiful day? With Tropical Boat, you can rent our boat WHITE SHARK 265 with 2 engines 150CV Yamaha...

4 to 8 hours Free Cancellation

5.0 (4)

from
$879

Welcome your Caribbean Holidays in a Private Luxury Party style, aboard a Sleek Party Bus, choose your favorite drinks from our Bottle Menu, Play your …More

Punta Cana, Dominican Republic

5.0 (29)

Party Bus Rental

Welcome your Caribbean Holidays in a Private Luxury Party style, aboard a Sleek Party Bus, choose your favorite drinks from our Bottle Menu, Play your...

2 to 6 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$900

Punta Cana Luxury Party Bus Private Group Rental

Our bus screams luxury. Completely renovated in 2021 with 3 air conditioning systems, a DJ booth with professional sound system, a bar with freezer, walls …More

5.0 (1)

Punta Cana Luxury Party Bus Private Group Rental

Our bus screams luxury. Completely renovated in 2021 with 3 air conditioning systems, a DJ booth with professional sound system, a bar with freezer, walls...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,200

Private Yacht Party Boat Rental Excursion in Ocho Rios, Jamaica

What to do in Ocho RIos on your cruise stop, day trip or during your stay? Our Hatteras 55' Yacht offers you a unique experience …More

Runaway Bay, Jamaica

5.0 (27)

Private Yacht Party Boat Rental Excursion in Ocho Rios, Jamaica

What to do in Ocho RIos on your cruise stop, day trip or during your stay? Our Hatteras 55' Yacht offers you a unique experience...

3 to 6 hours Hotel pickup offered Free Cancellation

5.0 (27)

from
$1,290

Fury is a Meticulously maintained vessel with professional, service oriented crew that has been on Island for decades. …More

5.0 (2)

Private Sunset Harbor Sail (25 Max)

Fury is a Meticulously maintained vessel with professional, service oriented crew that has been on Island for decades....

2 hours Free Cancellation

5.0 (2)

from
$1,500

St Thomas Full-Day Boat Rental 37' Intrepid Powerboat

Sonic Charters is able to accommodate groups up to 12 passengers on our top of the line power boats. We have five great powerboats to choose …More

Cruz Bay, US Virgin Islands

5.0 (36)

St Thomas Full-Day Boat Rental 37' Intrepid Powerboat

Sonic Charters is able to accommodate groups up to 12 passengers on our top of the line power boats. We have five great powerboats to choose...

4 to 8 hours Hotel pickup offered Free Cancellation

5.0 (36)

from
$1,600

Ocho Rios Private Deep Sea Fishing Boat rental Jamaica Fishing Tours and Charters for the casual or avid fishing enthusiast from the Ocho Rios Marina on …More

Ocho Rios, Jamaica

Private Deep Sea Fishing Boat Rental Ocho Rios Jamaica

Ocho Rios Private Deep Sea Fishing Boat rental Jamaica Fishing Tours and Charters for the casual or avid fishing enthusiast from the Ocho Rios Marina on...

4 hours

from
$1,600

Welcome aboard the H.R.H Mimosa, the only true luxury yacht charter in Montego Bay, Jamaica. We have taken our experience in delivering five-star villa service …More

Montego Bay, Jamaica

5.0 (2)

4-Hours Private Luxurious Yacht Snorkelling and Paddle Surf

Welcome aboard the H.R.H Mimosa, the only true luxury yacht charter in Montego Bay, Jamaica. We have taken our experience in delivering five-star villa service...

3 to 4 hours Free Cancellation

5.0 (2)

from
$3,000

Recenlty refurbished, ultra stylish, very comfortable charter boat now available in the British Virgin Islands, ready for you to experience. With new and efficient Mercury …More

Tortola, British Virgin Islands

5.0 (1)

Midnight Sun Charters - 43ft ORO

Recenlty refurbished, ultra stylish, very comfortable charter boat now available in the British Virgin Islands, ready for you to experience. With new and efficient Mercury...

7 hours Free Cancellation

5.0 (1)

from
$3,200

Our ultra stylish, and one of the most comfortable charter boats available in the US Virgin Islands at the moment, ready for you to experience. …More

Cruz Bay, US Virgin Islands

5.0 (25)

Midnight Sun Charters - 43ft ONYX

Our ultra stylish, and one of the most comfortable charter boats available in the US Virgin Islands at the moment, ready for you to experience....

7 hours Free Cancellation

5.0 (25)

from
$3,356

Icacos Island Private Charter with Snorkel Stops

Enjoy the boat for yourselves! This is a private boat just for you and your friends and family. We will Include on board Waters, sodas, …More

Luquillo, Puerto Rico

5.0 (2)

Icacos Island Private Charter with Snorkel Stops

Enjoy the boat for yourselves! This is a private boat just for you and your friends and family. We will Include on board Waters, sodas,...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$3,800

Perfect for Any Occasion Whether you're celebrating a special event or just looking for a private escape, our Private Catamaran tour is perfect for every …More

Ocho Rios, Jamaica

Private Group Cruise Catamaran Yacht Ocho Rios Jamaica

Perfect for Any Occasion Whether you're celebrating a special event or just looking for a private escape, our Private Catamaran tour is perfect for every...

4 hours

from
$4,065

Full-Day Luxury Boat Rental in St. Thomas and St. John Island

Hop aboard the only boat of its kind for day charter in the US Virgin Islands. With seating up to 18 (but group size capped …More

4.8 (54)

Full-Day Luxury Boat Rental in St. Thomas and St. John Island

Hop aboard the only boat of its kind for day charter in the US Virgin Islands. With seating up to 18 (but group size capped...

4 to 8 hours Free Cancellation

4.8 (54)

from
$4,500

Book your unforgettable yachting experience in the Dominican Republic. Amazing trip on a luxury private boat! Experience the perfect time on our 50 ft dayboat, …More

Punta Cana, Dominican Republic

5.0 (1)

Exclusive Yacht Rental in Punta Cana

Book your unforgettable yachting experience in the Dominican Republic. Amazing trip on a luxury private boat! Experience the perfect time on our 50 ft dayboat,...

1 day Hotel pickup offered

5.0 (1)

from
$4,935

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Caribbean Self-guided Tours & Rentals?

What are the best kid-friendly options for Caribbean Self-guided Tours & Rentals Tours?

Which Caribbean Self-guided Tours & Rentals have Instant Confirmation?

Which Caribbean Self-guided Tours & Rentals have Free Cancellation?

Caribbean Self-guided Tours & Rentals with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Caribbean Self-guided Tours & Rentals have Hotel Pickup?

Got any more Caribbean trip ideas?

What are the most popular styles of Tours and Activities in Caribbean?