Simpson Bay

We couldn't find any results for your search

Try searching something else or browse our destinations below.

Destinations

[[ result.label ]]

Homes

[[ result.label ]]

Popular Destinations

Orlando

Caribbean

Tennessee

Palm Springs

California

Barbados

Europe

United States 7200+ homes
- All United States 7200+ homes
- Florida 4800+ homes
  - All Florida 4800+ homes
  - Orlando 3400+ homes
    - All Orlando 3400+ homes
    - Reunion Resort 650+ homes
      - All Reunion Resort 650+ homes
      - Spectrum at Reunion 70+ homes
      - Bear's Den at Reunion 30+ homes
      - Eagle Trace At Reunion 10+ homes
      - Center Court Ridge 4 homes
      - Heritage Crossing 1 home
      - The Terraces Reunion 1 home
    - Champions Gate 450+ homes
    - Encore Resort at Reunion 350+ homes
    - Storey Lake Resort 350+ homes
    - Solterra Resort 250+ homes
      - All Solterra Resort 250+ homes
      - Villatel Village 70+ homes
    - Solara Resort 180+ homes
    - Margaritaville 150+ homes
    - Windsor Island Resort 150+ homes
    - Windsor at Westside Resort 130+ homes
    - Windsor Hills Resort 100+ homes
    - Vista Cay 60+ homes
    - Villatel Orlando Resort 60+ homes
    - Paradise Palms 50+ homes
    - Bella Vida 40+ homes
    - Windsor Palms 30+ homes
    - Formosa Valley Resort 30+ homes
    - Veranda Palms 20+ homes
    - Highlands Reserve 20+ homes
    - Watersong 20+ homes
    - Emerald Island Resort 20+ homes
    - Westhaven Resort 10+ homes
    - Le Reve Resort 10+ homes
    - Festival Resort 10+ homes
    - Sonoma Resort 10+ homes
    - Formosa Gardens 10+ homes
    - Lucaya Village 10+ homes
    - Providence 7 homes
    - Davenport 6 homes
    - Solana Resort 6 homes
    - Villa Domani Resort 5 homes
    - Magic Village 5 homes
    - West Lucaya Village 3 homes
    - Fantasy Island Resort 1 home
  - Cape Coral 400+ homes
  - Destin Area 350+ homes
    - All Destin Area 350+ homes
    - Destin 140+ homes
    - 30A 120+ homes
      - All 30A 120+ homes
      - Miramar Beach 60+ homes
      - Inlet Beach 10+ homes
      - Seagrove Beach 10+ homes
      - Seacrest Beach 6 homes
      - Rosemary Beach 5 homes
      - Seacrest 4 homes
      - Dune Allen Beach 4 homes
    - Santa Rosa Beach 80+ homes
  - Anna Maria Island 150+ homes
    - All Anna Maria Island 150+ homes
    - Bradenton Beach 70+ homes
    - Holmes Beach 60+ homes
  - Clearwater 60+ homes
  - Bradenton 50+ homes
  - Miami 50+ homes
  - Fort Lauderdale 40+ homes
  - Key West 30+ homes
  - West Palm Beach 30+ homes
  - Melbourne Beach 30+ homes
    - All Melbourne Beach 30+ homes
    - Harbor Island 20+ homes
  - Okaloosa Island 20+ homes
  - Charlotte Harbor 20+ homes
  - Fort Myers 10+ homes
    - All Fort Myers 10+ homes
    - Fort Myers Beach 2 homes
  - Panama City Beach 10+ homes
  - Delray Beach 10+ homes
  - Sarasota 9 homes
    - All Sarasota 9 homes
    - Longboat Key 5 homes
  - Pompano Beach 8 homes
  - Florida Keys 8 homes
    - All Florida Keys 8 homes
    - Islamorada 8 homes
  - Lighthouse Point 7 homes
  - Boynton Beach 6 homes
  - Deerfield Beach 5 homes
  - Boca Raton 4 homes
  - Lake Worth 4 homes
  - Rosemary Beach 3 homes
  - Boynton Beach 2 homes
  - Davie 2 homes
  - Perdido Key 2 homes
  - Clearwater Beach 1 home
  - Siesta Key 1 home
- California 850+ homes
  - All California 850+ homes
  - San Diego 250+ homes
  - Palm Springs 220+ homes
    - All Palm Springs 220+ homes
    - Palm Springs Central 70+ homes
    - Indio 50+ homes
    - La Quinta 50+ homes
    - Rancho Mirage 10+ homes
    - Palm Desert 10+ homes
    - Bermuda Dunes 4 homes
    - Indian Wells 3 homes
    - Coachella Valley 1 home
  - Lake Tahoe 120+ homes
  - Mammoth Lakes 60+ homes
  - Anaheim 30+ homes
  - Joshua Tree 30+ homes
  - Los Angeles 20+ homes
  - Malibu 20+ homes
  - La Jolla 10+ homes
  - Beverly Hills 10+ homes
  - Monterey 10+ homes
  - Yucca Valley 10+ homes
  - Pioneertown 3 homes
  - Encinitas 3 homes
  - Del Mar 3 homes
  - West Hollywood 3 homes
  - Coachella 1 home
  - Twentynine Palms 1 home
  - Cathedral City 1 home
  - Landers 1 home
- Tennessee 400+ homes
  - All Tennessee 400+ homes
  - Pigeon Forge 170+ homes
  - Gatlinburg 130+ homes
  - Sevierville 50+ homes
  - Nashville 30+ homes
  - Wears Valley 30+ homes
- Hawaii 190+ homes
  - All Hawaii 190+ homes
  - Big Island 100+ homes
  - Oahu 20+ homes
  - Honolulu 10+ homes
  - Maui 10+ homes
  - Kailua 10+ homes
  - Princeville 10+ homes
  - Koloa 9 homes
  - Haena 2 homes
  - Waimanalo 1 home
  - Waialua 1 home
  - Hanalei 1 home
- Texas 190+ homes
  - All Texas 190+ homes
  - Fredericksburg 50+ homes
  - New Braunfels 40+ homes
  - Canyon Lake 40+ homes
  - Rockport 30+ homes
  - Corpus Christi 10+ homes
  - Kerrville 3 homes
  - Llano 1 home
  - Aransas Pass 1 home
  - Stonewall 1 home
  - Taft 1 home
  - Blanco 1 home
- Arizona 170+ homes
  - All Arizona 170+ homes
  - Scottsdale 100+ homes
  - Phoenix 20+ homes
  - Tempe 10+ homes
  - Paradise Valley 9 homes
  - Mesa 5 homes
  - Gilbert 2 homes
  - Cave Creek 2 homes
  - Munds Park 1 home
  - Flagstaff 1 home
  - Glendale 1 home
  - Fountain Hills 1 home
- Utah 150+ homes
  - All Utah 150+ homes
  - Park City 150+ homes
- Colorado 110+ homes
  - All Colorado 110+ homes
  - Breckenridge 60+ homes
  - Estes Park 30+ homes
  - Steamboat Springs 10+ homes
  - Silverthorne 1 home
- Georgia 90+ homes
  - All Georgia 90+ homes
  - Big Canoe 30+ homes
  - Blue Ridge 20+ homes
  - Tybee Island 10+ homes
  - Blue Ridge 5 homes
  - Jasper 1 home
- Montana 60+ homes
  - All Montana 60+ homes
  - Big Sky 60+ homes
- Idaho 30+ homes
  - All Idaho 30+ homes
  - Sun Valley 30+ homes
- Nevada 10+ homes
- New Mexico 10+ homes
  - All New Mexico 10+ homes
  - Taos Ski Valley 10+ homes
- North Carolina 10+ homes
  - All North Carolina 10+ homes
  - Asheville 10+ homes
- South Carolina 9 homes
  - All South Carolina 9 homes
  - Sea Islands 9 homes
- Virginia 8 homes
  - All Virginia 8 homes
  - Hot Springs 8 homes
Caribbean 1600+ homes
- All Caribbean 1600+ homes
- St Barthelemy 450+ homes
  - All St Barthelemy 450+ homes
  - St Jean 50+ homes
  - Pointe Milou 40+ homes
  - Lurin 30+ homes
  - Gustavia 30+ homes
  - Flamands 30+ homes
  - Colombier 20+ homes
  - Marigot 20+ homes
  - Vitet 20+ homes
  - Anse des Cayes 10+ homes
  - Lorient 10+ homes
  - Toiny 10+ homes
  - Corossol 10+ homes
  - Petit Cul-de-Sac 10+ homes
  - Grand Cul-de-Sac 10+ homes
  - Gouverneur 10+ homes
  - Mont Jean 10+ homes
  - Deve 10+ homes
  - Camaruche 9 homes
  - Petite Saline 6 homes
  - Anse des Lezards 6 homes
  - Grand Fond 4 homes
  - Saline 2 homes
- Barbados 400+ homes
  - All Barbados 400+ homes
  - St. James 250+ homes
    - All St. James 250+ homes
    - Sandy Lane 50+ homes
    - Royal Westmoreland 40+ homes
    - Paynes Bay 30+ homes
    - Sugar Hill Resort 20+ homes
    - Reeds Bay 10+ homes
    - Fitts Village 10+ homes
    - Westmoreland 10+ homes
    - Porters 10+ homes
    - The Garden 8 homes
    - Holetown 8 homes
    - Glitter Bay 7 homes
    - Weston 4 homes
    - Carlton 3 homes
    - Prospect 3 homes
    - Lancaster 3 homes
    - Westmoreland Ridge 1 home
  - St. Peter 80+ homes
    - All St. Peter 80+ homes
    - Mullins Bay 20+ homes
    - Speightstown 20+ homes
    - Gibbes Beach 10+ homes
    - Gibbes Bay 3 homes
  - Christ Church 40+ homes
  - St. Lucy 2 homes
- Saint Martin 150+ homes
  - All Saint Martin 150+ homes
  - Terres Basses 50+ homes
  - Baie Rouge 10+ homes
  - Orient Bay 10+ homes
  - Cupecoy 10+ homes
  - Simpson Bay 10+ homes
  - Plum Bay 10+ homes
  - Baie Longue 9 homes
  - Indigo Bay 5 homes
  - Happy Bay 4 homes
  - Grand Case 2 homes
  - Cole Bay 2 homes
  - Pelican Key 2 homes
  - Anse Marcel 1 home
  - Nettle Bay 1 home
  - Guana Bay 1 home
- Dominican Republic 140+ homes
  - All Dominican Republic 140+ homes
  - Casa de Campo 90+ homes
  - Punta Cana 40+ homes
    - All Punta Cana 40+ homes
    - Punta Cana Resort & Club 20+ homes
    - Cap Cana 10+ homes
    - Cocotal Golf & Country Club 4 homes
  - Sosua 9 homes
  - Cabarete 2 homes
- Turks and Caicos 110+ homes
  - All Turks and Caicos 110+ homes
  - Providenciales 110+ homes
    - All Providenciales 110+ homes
    - Long Bay Beach 30+ homes
    - Grace Bay 30+ homes
    - Chalk Sound 10+ homes
    - Leeward Settlement 10+ homes
    - Babalua Beach 10+ homes
    - Turtle Cove 7 homes
    - Turtle Tail 5 homes
    - Thompson Cove 1 home
    - Turtle Creek 1 home
  - North Caicos 1 home
    - All North Caicos 1 home
    - Bottle Creek 1 home
- Jamaica 100+ homes
  - All Jamaica 100+ homes
  - Montego Bay 60+ homes
  - Ocho Rios 10+ homes
  - Discovery Bay 10+ homes
  - Runaway Bay 4 homes
  - Treasure Beach 1 home
  - Whitehouse 1 home
- Aruba 70+ homes
  - All Aruba 70+ homes
  - Noord 20+ homes
  - Malmok 10+ homes
  - Westpunt 10+ homes
  - Oranjestad-West 10+ homes
  - Oranjestad 6 homes
  - Palm Beach 4 homes
  - Savaneta 1 home
  - Eagle Beach 1 home
  - Santa Cruz 1 home
- Cayman Islands 60+ homes
  - All Cayman Islands 60+ homes
  - Rum Point 30+ homes
  - West Bay 6 homes
  - Old Man Bay 5 homes
  - George Town 4 homes
  - Bodden Town 4 homes
  - North Side 4 homes
  - Gun Bay 2 homes
  - Savannah 2 homes
- Saint Lucia 50+ homes
  - All Saint Lucia 50+ homes
  - Cap Estate 20+ homes
  - Rodney Bay 10+ homes
  - Marigot Bay 5 homes
  - Soufriere 5 homes
- Anguilla 30+ homes
- Grenada 10+ homes
- Saint Vincent and the Grenadines 7 homes
- Belize 1 home
- Antigua 1 home
Europe 1100+ homes
- All Europe 1100+ homes
- Italy 700+ homes
  - All Italy 700+ homes
  - Tuscany 300+ homes
    - All Tuscany 300+ homes
    - Siena 90+ homes
    - Florence 50+ homes
    - Arezzo 40+ homes
    - Pisa 30+ homes
    - Lucca 20+ homes
    - Grosseto 20+ homes
    - Livorno 10+ homes
    - Pistoia 10+ homes
    - Cortona 5 homes
    - Massa Carrara 3 homes
    - Prato 2 homes
    - Campiglia Marittima 1 home
    - Montecatini Val di Cecina 1 home
    - Palaia 1 home
    - Massarosa 1 home
    - Sarteano 1 home
    - Pomarance 1 home
  - Umbria 100+ homes
  - Sicily 70+ homes
  - Marche 40+ homes
  - Apulia 20+ homes
  - Sorrento Coast 20+ homes
  - Emilia-Romagna 20+ homes
  - Sardinia 20+ homes
  - Lazio 10+ homes
  - Piedmont 10+ homes
  - Amalfi Coast 10+ homes
  - Liguria 10+ homes
  - Lake Como 10+ homes
  - Lombardy 7 homes
  - Abruzzo 5 homes
  - Campania 4 homes
    - All Campania 4 homes
    - Capri 1 home
  - Puglia 4 homes
  - Veneto 3 homes
  - Venice 2 homes
  - Campalto 1 home
  - Montecarlo 1 home
  - Calabria 1 home
  - Ischia 1 home
- Greece 250+ homes
  - All Greece 250+ homes
  - Crete 50+ homes
    - All Crete 50+ homes
    - Chania 3 homes
    - Rethymno 2 homes
    - Gerani 1 home
  - Corfu 50+ homes
  - Mykonos 40+ homes
  - Kefalonia 40+ homes
  - Paxos 20+ homes
  - Santorini 10+ homes
  - Skopelos 8 homes
  - Paros 7 homes
  - Lefkada 5 homes
  - Zakynthos 4 homes
  - Alonnisos 2 homes
  - Meganisi 2 homes
  - Prinos 1 home
- Spain 80+ homes
  - All Spain 80+ homes
  - Mallorca 30+ homes
  - Ibiza 10+ homes
    - All Ibiza 10+ homes
    - San Carlos 3 homes
    - San Antonio 2 homes
    - San Jordi 2 homes
    - San Josep 2 homes
    - San Joan 2 homes
    - San Rafael 1 home
    - Santa Eularia 1 home
  - Andalusia 8 homes
    - All Andalusia 8 homes
    - Nerja 4 homes
    - Frigiliana 2 homes
  - Lanzarote 7 homes
  - Fuerteventura 6 homes
  - Menorca 6 homes
  - Costa Blanca 3 homes
  - Marbella 2 homes
  - Tenerife 1 home
- Croatia 30+ homes
  - All Croatia 30+ homes
  - Brac 10+ homes
  - Split-Dalmatia 9 homes
  - Hvar 4 homes
  - Ciovo 3 homes
  - Dubrovnik-Neretva 2 homes
- United Kingdom 30+ homes
  - All United Kingdom 30+ homes
  - Kent 30+ homes
    - All Kent 30+ homes
    - Canterbury 10+ homes
    - Margate 6 homes
    - Broadstairs 4 homes
    - Ramsgate 3 homes
    - Lyminge 3 homes
    - Wickhambreaux 1 home
    - Whitstable 1 home
- Portugal 10+ homes
  - All Portugal 10+ homes
  - Algarve 10+ homes
- Cyprus 6 homes
Central America 240+ homes
- All Central America 240+ homes
- Costa Rica 130+ homes
  - All Costa Rica 130+ homes
  - Playa Herradura 50+ homes
  - Tamarindo 30+ homes
  - Hacienda Pinilla 10+ homes
  - Playa Conchal 3 homes
  - Herradura Bay 3 homes
  - Playa Hermosa 2 homes
  - Playa Grande 1 home
  - Osa Peninsula 1 home
  - Playa Flamingo 1 home
- Mexico 100+ homes
  - All Mexico 100+ homes
  - Cabo 90+ homes
  - La Paz 10+ homes
  - Cancun 1 home
Asia 220+ homes
- All Asia 220+ homes
- Thailand 150+ homes
  - All Thailand 150+ homes
  - Koh Samui 110+ homes
    - All Koh Samui 110+ homes
    - Bophut 20+ homes
    - Chaweng 10+ homes
    - Bang Por 10+ homes
    - Lipa Noi 10+ homes
    - Maenam 10+ homes
    - Taling Ngam 7 homes
    - Laem Sor 5 homes
    - Choeng Mon 5 homes
    - Bangrak 4 homes
    - Lamai 4 homes
    - Laem Sett 3 homes
    - Plai Laem 2 homes
    - Nathon 2 homes
    - Tongson Bay 2 homes
    - Chaweng Noi 1 home
  - Phuket 30+ homes
    - All Phuket 30+ homes
    - Phang Nga 10+ homes
    - Kamala 10+ homes
    - Nai Thon 4 homes
    - Surin 3 homes
    - Cape Yamu 3 homes
  - Chiang Mai 1 home
- Indonesia 70+ homes
  - All Indonesia 70+ homes
  - Bali 70+ homes
    - All Bali 70+ homes
    - Canggu 20+ homes
    - Seminyak 20+ homes
    - Bukit 7 homes
    - Samur Ketewel 6 homes
    - Seseh Tanah Lot 6 homes
    - Tabanan 3 homes
    - Jimbaran 2 homes
    - Ubud 2 homes
    - Candidasa 2 homes
    - Nusa Lembongan 2 homes
    - Umalas Keroboken 1 home
    - Nusa Dua 1 home

[[ _LC.models.mainDatepicker.dates.checkin.format('Do MMM YYYY') || 'Check in' ]] [[ _LC.models.mainDatepicker.dates.checkout.format('Do MMM YYYY') || 'Check out' ]]

Vacation homes in Simpson Bay

[[_LC.models.shadowArray.length - _LC.models.budgetPlus.length || '...']] homes found in Simpson Bay

[[ _LC.visualToggle.showDescription ? 'Show less' : 'Read more about Simpson Bay' ]]

Hailed as one of the most beautiful beaches in the Caribbean, Simpson Bay is a great choice for a dream island vacation. With its wide sandy bays and sparkling blue seas, Simpson Bay is a paradise setting, ideal for couples, families and groups on vacation. Simpson Bay vacation rentals are perched in idyllic hillside and beachfront locations, with private pools, generous living spaces and breathtaking ocean views.

These homes are part of the world's leading villa collection World Travel Awards Winner

We're experiencing very high levels of interest in our properties right now. Please refresh the page to try that search again.

Only [[ _LC.percentageLeft ]][[ _LC.percentageLeftSymbol === '%' ? _LC.percentageLeftSymbol + ' of listings' : ' properties']] are left for these dates matching your criteria. We recommend booking a place soon.

Showing [[_LC.models.chunkArray.length]] out of [[_LC.models.shadowArray.length]] homes

No vacation homes found. Try widening your search criteria.

Popular Destinations

North America

Central America

Caribbean

Europe

Asia

Popular Collections

Collections

Orlando Resorts

Vacation Rentals by Size

Vacation homes in Simpson Bay

[[_LC.models.shadowArray.length - _LC.models.budgetPlus.length || '...']] homes found in Simpson Bay

Popular Destinations

North America

Central America

Caribbean

Europe

Asia

Popular Collections

Collections

Orlando Resorts

Vacation Rentals by Size

Availability

[[_LC.models.enquiryProperty.name]]

from [[ (_LC.models.enquiryProperty.from.abta || _LC.models.enquiryProperty.from.basic) / 7 | currency:'$':2 ]] per night

Call us for rates

Luxury Travel Planners

Vacation homes in Simpson Bay

[[_LC.models.shadowArray.length - _LC.models.budgetPlus.length || '...']] homes found in Simpson Bay