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Vacation rentals in Prickley Pear Cays

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Prickley Pear Cays

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

Guest favorite

Condo in Meads Bay, Anguilla

5.0 out of 5 average rating, 20 reviews

1 Bedroom Luxury Condo Seconds to Beach + Terrace & Hot Tub

Tranquility Beach Anguilla is Anguilla’s newest beach resort on top-rated Meads Bay Beach on the West End and was voted Best Boutique Hotel in Anguilla 2023. Everything you need for an ultimate beach vacation is at your doorstep and our award-winning staff is at your service. Swim and snorkel in turquoise waters. Walk to resorts, spas and top restaurants. This unit is professionally managed by our friendly resort staff including property manager, concierge team, housekeepers and beach butlers.

Aug 28 – Sep 4

R9,386 ZAR per night
Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 35 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

SPECIAL: MARCH 18-30 @ $800/NIGHT Guaranteed to create a 5-Star experience! Fully air-conditioned 3 BR, 3 1/2 bath Beachfront Villa w/private pool. If you love the ocean & spectacular views, but fine living & comfort are important to you, we have it all! My home offers Personal housekeeper, Private Chef for hire, full Concierge Service, private garage, and gym. Also, food and groceries delivered prior to your arrival, access to all the services and amenities next door at the Oyster Bay Hotel.

May 14 – 21

R19,042 ZAR per night
Superhost

Apartment in Simpson Bay, Sint Maarten

4.87 out of 5 average rating, 177 reviews

Apartment on the beach

Let this tranquil, centrally located, 1 bedroom apartment become your home away from home. This beachfront property is located on the BEST and WIDEST stretch of Simpson Bay beach with gentle waves and no rocks, which makes it a perfect spot for swimming. Although this property is tucked away, and there are never many people on this part of the beach, it is in a heart of Simposn Bay. Simpson Bay beach offers one of the longest stretches of uninterrupted sandy, white coastline on Sint Maarten.

Sep 26 – Oct 3

R3,011 ZAR per night

Popular amenities for Prickley Pear Cays vacation rentals

Other great vacation rentals in Prickley Pear Cays

Superhost

Home in Shoal Bay Village, Anguilla

4.92 out of 5 average rating, 13 reviews

Shoal Bay Coastal Sanctuary, Anguilla

Mar 4 – 11

R12,988 ZAR per night
Superhost

Home in Island Harbour, Anguilla

5.0 out of 5 average rating, 4 reviews

Oceanfront Villa With Pool and Spa Near Shoal Bay

Aug 24 – 31

R8,514 ZAR per night
Guest favorite

Home in Cul de Sac, St. Martin

5.0 out of 5 average rating, 44 reviews

villa koala saint martin un petit coin de paradis

Oct 3 – 10

R7,800 ZAR per night
Guest favorite

Condo in Simpson Bay, Sint Maarten

5.0 out of 5 average rating, 53 reviews

Beach front luxury! Huge 2BR that has it all! 😍🤩😍

Feb 17 – 24

R16,611 ZAR per night
Guest favorite

Apartment in Mount Fortune, Anguilla

5.0 out of 5 average rating, 45 reviews

Fortune Estate (Car rental available)

Dec 15 – 22

R2,525 ZAR per night
Guest favorite

Guest suite in Cul-de-Sac, St. Martin

4.91 out of 5 average rating, 43 reviews

Cozy apartment, private pool & terrace

Sep 23 – 30

R2,061 ZAR per night
Guest favorite

Home in Les Terres Basses, St. Martin

5.0 out of 5 average rating, 8 reviews

Luxury Bungalow Sea & Pool View

Oct 22 – 29

R4,359 ZAR per night
Guest favorite

Apartment in Grand-Case, St. Martin

4.92 out of 5 average rating, 72 reviews

lovely 1 bedroom beach front property

Aug 19 – 26

R2,104 ZAR per night
Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

4.96 out of 5 average rating, 98 reviews

The Blue Door Villa - 4 bed ocean view home

Aug 2 – 9

R17,279 ZAR per night
Guest favorite

Home in Shoal Bay, Anguilla

5.0 out of 5 average rating, 12 reviews

Harmony at Bayview Homes

Dec 24 – 31

R9,930 ZAR per night
Guest favorite

Villa in Upper Prince's Quarter, Sint Maarten

5.0 out of 5 average rating, 20 reviews

Villa Blue Roc

Sep 7 – 14

R10,393 ZAR per night
Superhost

Villa in Seafeathers, Anguilla

4.83 out of 5 average rating, 6 reviews

Oceanview villa with private pool, 5 mins to beach

Sep 7 – 14

R7,555 ZAR per night