Best Vacation Homes in Pelican Key
Villa
10.0(75 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
R10,645/Night
7 Nights - R74,505
House
10.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
13993.08 ft²
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
R13,266/Night
7 Nights - R92,863
R21,234/Night
7 Nights - R148,631
Villa
10.0(52 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Pool
- Ocean View
- Balcony/Terrace
View
R4,876/Night
7 Nights - R34,130
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Parking
Air Conditioner
Internet
Child Friendly
R3,593/Night
7 Nights - R25,148
Villa
10.0(44 Reviews)
3 Bedrooms
2 Baths
6 Guests
2153 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R12,426/Night
7 Nights - R86,980
Condo
10.0(29 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R3,637/Night
7 Nights - R25,461
Villa
10.0(27 Reviews)
8 Bedrooms
7 Baths
18 Guests
5597 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R14,749/Night
7 Nights - R103,246
Pelican Key Luxury Rentals
Villa
7 Bedrooms
8 Baths
14 Guests
Fireplace/Heating- Air Conditioner
- Internet
- Child Friendly
R95,583/Night
7 Nights - R669,079
House
10.0(1 Review)
6 Bedrooms
7 Baths
14 Guests
6000 ft²
- Balcony/Terrace
Kitchen- Parking
- Air Conditioner
R82,710/Night
7 Nights - R578,967
Villa
8 Bedrooms
9 Baths
16 Guests
5995.5 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R57,829/Night
7 Nights - R404,809
Villa
10.0(1 Review)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R26,060/Night
7 Nights - R182,415
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
2153 ft²
- Kitchen
- Parking
- Air Conditioner
- Internet
R22,201/Night
7 Nights - R155,404
Villa
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R21,395/Night
7 Nights - R149,768
House
4 Bedrooms
4 Baths
8 Guests
2691 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R20,723/Night
7 Nights - R145,071
House
10.0(6 Reviews)
5 Bedrooms
5 Baths
10 Guests
13993 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R19,975/Night
7 Nights - R139,831
Pelican Key Pet Friendly Vacation Rentals
House
10.0(6 Reviews)
4 Bedrooms
4 Baths
6 Guests
- Pool
- Balcony/Terrace
Pet Friendly- Kitchen
R10,712/Night
7 Nights - R74,983
Villa
9.1(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
1291.67 ft²
Private Beach- Oceanfront
- Pool
- Ocean View
R7,251/Night
7 Nights - R50,758
Villa
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R14,359/Night
7 Nights - R100,510
Apartment
7.9(16 Reviews)
1 Bedroom
1 Bath
3 Guests
548.96 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,049/Night
7 Nights - R14,337
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
Hot Tub- Pool
- Ocean View
- Balcony/Terrace
R6,158/Night
7 Nights - R43,095
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R4,473/Night
7 Nights - R31,312
Villa
9.8(30 Reviews)
5 Bedrooms
4 Baths
10 Guests
2600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R19,734/Night
7 Nights - R138,133
Villa
9.8(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R4,466/Night
7 Nights - R31,262
Pelican Key Large Vacation Homes
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
2200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R5,718/Night
7 Nights - R40,029
Villa
10.0(1 Review)
1 Bedroom
3 Baths
8 Guests
1700.7 ft²
- Pool
- Balcony/Terrace
- View
- Parking
R9,419/Night
7 Nights - R65,936
Villa
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R3,911/Night
7 Nights - R27,373
Apartment
7.9(899 Reviews)
20 Bedrooms
4 Baths
16 Guests
336.37 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R2,661/Night
7 Nights - R18,639
Villa
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Air Conditioner
- Internet
R2,632/Night
7 Nights - R18,424
Villa
10.0(2 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Kitchen
- Parking
R8,177/Night
7 Nights - R57,234
Villa
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
R11,934/Night
7 Nights - R83,536
Villa
9.8(81 Reviews)
3 Bedrooms
1 Bath
6 Guests
2850 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R10,382/Night
7 Nights - R72,676
Why Choose Rent By Owner for your Pelican Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Pelican Key Vacation Rentals
Where are the best neighborhoods to stay in Pelican Key?
Pelican Key in Simpson Bay offers a vibrant and picturesque setting for your stay, featuring a variety of convenient locations that cater to different preferences. Whether you’re seeking the tranquility of beachfront properties or the lively atmosphere of nearby amenities, this neighborhood provides an ideal backdrop for your Sint Maarten vacation. With its accessible location within Simpson Bay, Pelican Key ensures you are close to the island’s best attractions while maintaining a peaceful environment. When booking through trusted platforms, you'll find a range of comfortable options designed to enhance your experience in this beautiful part of Sint Maarten.
Cay Bay
In this part of the region, you can enjoy a peaceful atmosphere while being close to the area's vibrant amenities. It’s an ideal spot for travelers seeking a tranquil retreat with convenient access to local attractions and pristine beaches.
View 1434+ Rentals in Cay BaySimpson Bay
This lively neighborhood offers a perfect blend of relaxation and entertainment, making it a favorite among visitors looking to immerse themselves in the local culture. Here, you'll find stylish vacation rentals that place you near beautiful waterfront views and popular dining options.
View 424+ Rentals in Simpson BayBest Times to Visit Pelican Key
When should you plan your Vacation Rentals stay?
Timing your visit to Pelican Key in Simpson Bay allows you to experience this tropical paradise at its best, with considerations for peak seasons and weather patterns ensuring a memorable and enjoyable stay.
Peak Season Highlights
December to April
This period marks the peak season when visitors flock to the area for its warm weather and lively atmosphere, making it an ideal time to secure your vacation rental.
Average Temperature Daytime: 28°C (82°F) - Nighttime: 21°C (70°F)
June to August
During summer months, the region experiences high demand as travelers enjoy sunny days and vibrant events, so early booking is recommended for your preferred vacation rentals.
Average Temperature Daytime: 30°C (86°F) - Nighttime: 24°C (75°F)
Off-Season Highlights
May to June
This shoulder season offers fewer crowds and more flexible availability, making it a great time to find affordable vacation rentals and enjoy quieter beaches.
Average Temperature Daytime: 29°C (84°F) - Nighttime: 22°C (72°F)
September to November
The area sees lower visitor numbers during these months, providing a peaceful retreat with plentiful options for vacation rentals at attractive rates.
Average Temperature Daytime: 29°C (84°F) - Nighttime: 23°C (73°F)
Weekly Weather Forecast for Pelican Key
How to Book Your Pelican Key Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Pelican Key
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool for relaxing and swimming in the warm Caribbean sun.
- Take advantage of lush, landscaped gardens that create a serene outdoor atmosphere.
- Make use of spacious patios or balconies ideal for outdoor dining and entertaining.
- Benefit from direct access to nearby beaches, perfect for sunbathing and water activities.
- Utilize outdoor grills for hosting barbecues amidst tropical surroundings.
- Experience well-maintained walking paths or jogging trails within the property grounds.
- Relax in shaded lounge areas designed for unwinding while enjoying scenic views of the destination.
Top Attractions Around Pelican Key
What attractions are nearby?
During your stay here, you'll find plenty of nearby activities to enjoy, from relaxing on beautiful beaches to exploring vibrant local dining and entertainment options in the region.
Family Activities
- Snorkeling at Maho Bay: Discover vibrant marine life and crystal-clear waters just a short trip from your Pelican Key accommodation, perfect for family-friendly underwater adventures.
- Sunset Sailing Tours: Experience breathtaking sunsets over the Caribbean Sea aboard a family-oriented sailing tour, making for unforgettable memories here in the region.
- Explore Simpson Bay Lagoon: Engage in calm, shallow waters ideal for paddleboarding or kayaking, offering safe and fun aquatic activities suitable for all ages.
- Visit local beaches: Relax and play on pristine sands at nearby beaches where gentle waves and scenic surroundings provide the perfect setting for family outings in this area.
Adult Activities
- Sailing and Yacht Charters: Experience the thrill of exploring the waters surrounding the area on a private sailing or yacht charter, perfect for enjoying the scenic coastline and vibrant marine life.
- Relaxing Beach Days: Spend your day lounging on pristine beaches, where crystal-clear waters and soft sands offer a peaceful retreat just moments from your vacation rental.
- Nightlife and Sunset Cruises: Enjoy the lively nightlife scene or book a sunset cruise that offers unforgettable views while you unwind with signature cocktails.
- Water Sports Adventures: Engage in exhilarating water sports such as jet skiing, paddleboarding, or snorkeling right here, making the most of the calm Caribbean waters.
Other Places to Stay in Pelican Key
Flamingo Beach
Hollywood Casino
Lay Bay Beach
Pelican Key Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Sampling the region’s authentic cuisine will enrich your stay and give you a true taste of this destination’s vibrant culture.
- Plan outdoor activities early in the day: Taking advantage of the area's pleasant weather allows you to enjoy beaches and water sports without the midday crowd.
- Utilize local transportation services: Making use of convenient transport options helps you easily access key spots and explore the region at your own pace.
- Respect local customs and environment: Being mindful of the community and natural surroundings ensures a responsible visit that preserves the area’s beauty for future travelers.
Transportation Options
- Car Rentals: Local car rental services offer convenient mobility, allowing you to explore the area and its stunning surroundings at your own pace during your stay.
- Taxis and Ride-Sharing Services: Reliable taxis and ride-sharing options provide quick, hassle-free transportation within this destination, making it easy to access popular spots and amenities.
- Public Buses: Public bus routes connect key parts of the region, offering an affordable and eco-friendly way to get around and experience the local vibe.
- Private Transfers and Shuttle Services: Customized transfer services can be arranged for seamless, comfortable journeys between the airport, your accommodation, and nearby attractions here.
Local Customs Options
- Greetings and Respect: In this tropical destination, it’s customary to greet others with a friendly handshake or a warm 'Good morning' to show respect and friendliness.
- Language Etiquette: While English is widely spoken, locals appreciate polite greetings and basic phrases in Dutch or Patois as a sign of cultural appreciation.
- Celebrating Local Festivals: Participating respectfully in local festivals and events highlights your interest in the region's vibrant traditions and community spirit.
- Dress Code for Religious Sites: When visiting churches or religious sites here, modest dress is expected to honor local customs and maintain decorum.
Frequently Asked Questions About Pelican Key?
1. What are the top vacation rentals in Pelican Key?
There are a lot of options in Pelican Key. If you plan on staying in the Pelican Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pelican Key:
- WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
- Oceanfront villa with breathtaking views–2BR/2BA in Pelican Key, Simpson Bay
- Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
- ENJOY THE BEAUTY OF ST MAARTEN BY STAYING RIGHT ON THE OCEAN IN LUXURY CONDO
- Villa Seaclusion accommodates 18 guests 9 beds 5 villas Ocean view pool
- very nice condo full equiped
- Stunning 2BD oceanfront villa; spacious, modern, and close to restaurants/bars
- New Listing, Exceptional 3 bed & bath with private pool in Pelican Cove
- A breath of fresh air right on the sea - relax and enjoy!
- Peaceful Paradise
2. How many vacation rentals have private pools in Pelican Key?
There are 42 vacation rentals with private pools near Pelican Key. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Pelican Key are best for families?
If you are looking for a family-friendly vacation home in Pelican Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pelican Key:
4. How many Rentbyowner vacation rentals are available in Pelican Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 165 in the Pelican Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pelican Key.
5. What is the cancellation policy for vacation rentals in Pelican Key, Simpson Bay?
The cancellation policy varies depending on the property listing. You should review the specific terms outlined in the booking details or contact the property owner directly to understand the cancellation options available.
6. How do I inquire about amenities and availability for rental properties in this region?
You can use the booking platform to send inquiries directly to property owners. It's recommended to review the listing description for details about amenities and confirm availability by reaching out through the messaging system provided.
7. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning fees, security deposits, or service charges are typically listed on each property’s page. Be sure to check the specific listing details or contact the owner for comprehensive information on extra costs.
8. What is the check-in and check-out process for vacation rentals in this area?
Check-in and check-out procedures are specified in each property listing. Owners may offer flexible times or require specific instructions, so it’s best to review the details or ask the host directly to ensure a smooth arrival and departure.
9. Is it possible to modify my reservation after booking a vacation rental near Simpson Bay?
Reservation modifications depend on the property's policies. Contact the owner or support through the booking platform to request changes, and they will advise you on the possibilities and any applicable fees.
Pelican Key Top Rated Vacation Rentals
Apartment
10.0(19 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R2,323/Night
7 Nights - R16,266
House
10.0(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R6,500/Night
7 Nights - R45,501
Apartment
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
377 ft²
- Pool
- Ocean View
- View
- Kitchen
R1,915/Night
7 Nights - R13,398
Condo
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
R8,085/Night
7 Nights - R56,592
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Kitchen
- Parking
R3,626/Night
7 Nights - R25,379
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R3,131/Night
7 Nights - R21,918
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R2,802/Night
7 Nights - R19,611
Villa
9.8(46 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R5,768/Night
7 Nights - R40,375
