Vacation Rentals & Villas in Guana Bay

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2,825 Houses

(4) Excellent 

25

Villa Fleur De Mer. Sint Maarten Bit of Paradise at introductory prices

Sint Maarten / Guana Bay

Guana Bay villa

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool

Price per night from

$230

Price per night from

$230

Great rentals within 20 miles that match your search

Distance approx 13.82 km from Guana Bay

(5) Excellent 

27

Reality Stops Here: Deluxe New 2BR Villa, 23 ft / 7m Heated Pool Over Atlantic

St. Barthelemy / Colombier

Colombier villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$429

Price per night from

$429

Distance approx 4.77 km from Guana Bay Show on Map

(48) Excellent 

52

studio pinel

Saint-Martin / Cul de Sac

Cul de Sac apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$139

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$139

Distance approx 4.66 km from Guana Bay Show on Map

22

Villa Del Mar, Anse Marcel - Fabulous Ocean View

Saint-Martin / Anse Marcel

Anse Marcel villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$656

Price per night from

$656

Distance approx 4.85 km from Guana Bay Show on Map

(5) Excellent 

26

Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Child Friendly

Price per night from

$374

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$374

Distance approx 10.59 km from Guana Bay

(16) Excellent 

14

Mainstay Villa at Elsie Bay

Anguilla

Anguilla villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Ask about pets

Price per night from

$299

Responds fast!
avg. 3 hours 25 minutes

Price per night from

$299

Distance approx 3.88 km from Guana Bay Show on Map

12

Sea view apartment of 1076 sq ft at Mont Vernon

Saint-Martin / Orient Bay

Orient Bay apartment

1 7 5 nights min

  • 1 bedroom
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$92

Price per night from

$92

Distance approx 4.73 km from Guana Bay Show on Map

(1) Excellent 

15

BEACHFRONTBLISS

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Ask about pets

Price per night from

$346

Price per night from

$346

Distance approx 16.8 km from Guana Bay

23

Villa Moorea Saint-Barthelemy

St. Barthelemy / Marigot

Marigot house

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$519

Price per night from

$519

Distance approx 2.16 km from Guana Bay Show on Map

33

1 or 2 weeks in condo 5 * St. Marteen seaview

Sint Maarten / Philipsburg

Philipsburg apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$460

Price per night from

$460

Distance approx 15.77 km from Guana Bay

26

Villa Eden Island, 3 bedroom

St. Barthelemy / Gustavia

Gustavia villa

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Ask about children

Price per night from

$987

Price per night from

$987

Distance approx 4.98 km from Guana Bay Show on Map

32

Barefoot Oceanfront Condo St Maarten

Simpson Bay / Simpson Bay Beach

Simpson Bay villa

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$307

Price per night from

$307

Distance approx 12.51 km from Guana Bay

4

Gardenia Villa at Indigo Reef

Anguilla / The Valley

The Valley villa

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Nearest beach 0.9 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$374

Price per night from

$374

Distance approx 12.78 km from Guana Bay

(18) Excellent 

20

Little Butterfly

Anguilla / The Valley

The Valley apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Ask about children
“The Little Butterfly that Soars!” We recently visited the beautiful island of anguilla for the third time and stayed at the Little Butterfly for the first time...and it certainly won't be our last! It's a rare gem of stunning accommodations and excep
…see more

Price per night from

$284

Price per night from

$284

Distance approx 9.97 km from Guana Bay

13

Champagne Shores Villa

Anguilla / Blowing Point

Blowing Point villa

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,957

Price per night from

$1,957

Distance approx 12.45 km from Guana Bay

36

Luxurious and Exclusive Beachfront Property

Anguilla / West End Village

West End Village villa

9 18 min stay varies

  • 9 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$14,377

Responds fast!
avg. 3 minutes

Price per night from

$14,377

Distance approx 17.72 km from Guana Bay

15

The Quintessential Villa in Serenity - Anse Toiny

St. Barthelemy / Toiny

Toiny villa

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$2,494

Price per night from

$2,494

Distance approx 4.65 km from Guana Bay Show on Map

10

New Opening "VILLA JWI LAVI" Sea view Terrace Suite "VANILLA" with Breakfast

Saint-Martin / Cul de Sac

Cul de Sac guest house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$171

Price per night from

$171

Distance approx 2.67 km from Guana Bay Show on Map

38

Divi LIttle Bay Beach St Maarten Studio 1BA Suite

Sint Maarten / Philipsburg

Philipsburg apartment

2 2 7 nights min

  • 2 bedrooms
  • sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$172

Responds fast!
avg. 59 minutes

Price per night from

$172

Distance approx 13.24 km from Guana Bay

49

Award Winning Ocean Front Villa Estate

Anguilla

Anguilla house

9 10 min stay varies

  • 9 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$7,243

Responds fast!
avg. 3 minutes

Price per night from

$7,243

Distance approx 4.42 km from Guana Bay Show on Map

17

New - a Two Hundred Million Dollar Yacht on Land

Sint Maarten / Philipsburg

Philipsburg villa

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$353

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$353

Distance approx 7.55 km from Guana Bay Show on Map

20

Villa Friends

Saint-Martin / Terres Basses

Terres Basses villa

14 22 3 nights min

  • 14 bedrooms
  • sleeps 22
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,738

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$4,738

Distance approx 7.14 km from Guana Bay Show on Map

22

Cupecoy Beach Club

Sint Maarten / Cupecoy Bay

Cupecoy Bay condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$346

Price per night from

$346

Distance approx 6.63 km from Guana Bay Show on Map

5

2 Bedroom Oceanfront-Belair Beach Resort

St. Martin Sint Maarten

St Martin / St Maarten apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$302

Price per night from

$302

Distance approx 6.56 km from Guana Bay Show on Map

8

Modern Blue Residence one bedroom Condo, Cupecoy, Sint Maarten

Sint Maarten / Philipsburg

Philipsburg apartment

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$288

Responds fast!
avg. 41 minutes

Price per night from

$288

Distance approx 6.81 km from Guana Bay Show on Map

23

Crepuscule Villa

Saint-Martin / Terres Basses

Terres Basses villa

5 12 1 night min

  • 5 bedrooms
  • sleeps 12
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$3,502

Price per night from

$3,502

Distance approx 3.64 km from Guana Bay Show on Map

(2) Average 

7

Dream pool beach vacation

Saint-Martin / Orient Bay

Orient Bay condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$92

Price per night from

$92

Distance approx 4.99 km from Guana Bay Show on Map

8

Studio Baie Nettle in the hotel complex "Les Flamboyants"

Saint-Martin / Baie Nettle

Baie Nettle studio

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$92

Price per night from

$92

Distance approx 16.27 km from Guana Bay

20

La Plage

Windward / Lorient

Lorient villa

7 14 7 nights min

  • 7 bedrooms
  • sleeps 14
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$8,884

Responds fast!
avg. 3 hours 20 minutes

Price per night from

$8,884

Distance approx 3.07 km from Guana Bay Show on Map

12

Villa LEMON -In a green area at the entrance to Orient Bay

Saint-Martin / Orient Bay

Orient Bay villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly

Price per night from

$675

Price per night from

$675

Distance approx 3.33 km from Guana Bay Show on Map

33

Veronica Villa, 3 rooms in Orient Bay

Saint-Martin / Orient Bay

Orient Bay house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$460

Price per night from

$460

Distance approx 3.43 km from Guana Bay Show on Map

26

Macassi 4, villa with private pool on the beach

Saint-Martin / Orient Bay

Orient Bay villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 2.55 km from Guana Bay Show on Map

7

Paradise on Earth!

Saint-Martin / Cul de Sac

Cul de Sac villa

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden
Inquire for Rates
Inquire for Rates

Distance approx 5.21 km from Guana Bay Show on Map

12

Studio feet in the water

Saint-Martin / Marigot, Saint Martin

Marigot, Saint Martin studio

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
Inquire for Rates
Inquire for Rates

Distance approx 4.91 km from Guana Bay Show on Map

(10) Excellent 

17

Paradise Found at Las Arenas - Beachfront Luxury!

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Paradise Found discribes this condo perfectly” The condo was perfect well stocked with everything you could ever need.The location was excellent on what I consider to be one of the best beaches on the island. The owner Nancy was more then accommodatin
…see more

Price per night from

$411

Price per night from

$411

Distance approx 16.28 km from Guana Bay

17

Sand Castle - 4 Bedrooms at Lorient - Book Now

St. Barthelemy / Anse de Lorient

Anse de Lorient villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$1,438

Price per night from

$1,438

Distance approx 16.36 km from Guana Bay

15

**PLEASE ASK ABOUT OUR SPEICAL OFFERS** Zen - Stunning Ocean Views - 2 Bedrooms

St. Barthelemy / St. Jean

St. Jean villa

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$1,006

Price per night from

$1,006

Distance approx 0.1 km from Guana Bay Show on Map

7

Suite 6/8 pers au Westin Dawn Beach ST Marteen

Sint Maarten / Oyster Pond

Oyster Pond hotel apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$495

Price per night from

$495