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Posh Waterfront Wyndham Hotel in Cabo San Lucas

Wyndham Cabo San Lucas by Tesoro Resorts

Cabo San Lucas, Mexico

Centrally located resort with outdoor pool, onsite dining, and spa overlooking the Cabo San Lucas marina

$462 $209

Resort near Palm Springs

Indian Wells Resort Hotel

Indian Wells, CA

Site of the original Bob Hope Chrysler Classic, this retro-chic hotel features renowned courses and a Rat Pack–inspired lounge

$101 $49

All-Inclusive Cancun Resort

All-Inclusive Grand Oasis Cancun

Mexico

All-inclusive resort in Cancun’s Hotel Zone features themed beach parties and the longest pool in Cancun

$462 $189

Oceanfront Villas on St. Thomas

Crystal Cove Villas

St. Thomas, US Virgin Islands

A resort on an award-winning St. Thomas beach offers condo-style villas, a saltwater pool, and dining and jet-boating credits

$635 $349

All-Inclusive Resort Steps from Caribbean Beach

IFA Villas Bávaro Resort & Spa

Punta Cana, Dominican Republic

All-inclusive Dominican Republic resort steps from white-sand Bávaro Beach; property features two pools and ample dining options

$504 $299

Beachfront Island Resort in Belize

Exotic Caye Beach Resort

Belize

Spacious condos and suites, many with balconies facing the Caribbean Sea and the resort's private stretch of white-sand beach

$545 $359

Private 4-Star Casitas in Costa Rica Jungle

Rio Celeste Hideaway Hotel

Costa Rica

A 4-star eco-resort near famous sky-blue Rio Celeste and amid tropical jungle, with pool with swim-up bar, Costa Rican restaurant, and spa.

$917 $299

Eco Resort in Costa Rican Rainforest

Blue River Resort & Hot Springs

Guancaste

Eco-adventure resort amid Costa Rica's mountains and jungles; getaway includes two activities, such as ziplining or water tubing

$546 $279

4-Star Beachfront Hotel in Puerto Rico’s Capital

San Juan Water Beach Club Hotel

San Juan, Puerto Rico

Trendy four-star hotel near the beach in Puerto Rico’s capital features relaxing rooms, a rooftop lounge, and ocean views

$675 $419

Beachfront Villas on St. Lucia

Windjammer Landing Villa Beach Resort

St. Lucia

Walk from your villa to the beach, where you can enjoy complimentary water-sports rentals; five restaurants onsite

$1,260 $499

4-Star, All-Inclusive Caribbean Resort

AlSol Del Mar Cap Cana

Cap Cana, Dominican Republic

All-inclusive resort with direct beach access, oceanfront infinity pool, and gourmet restaurants and bars

$2,274 $799

Palm Desert Inn near Popular Shopping District

Inn at Deep Canyon

Palm Desert, CA

Hotel is steps from popular El Paseo shopping strip; offers outdoor pool and complimentary hot breakfast

$79 $55

Surf-Inspired Inn on Mexico's Pacific Coast

The Inn at Manzanillo Bay

Troncones, Mexico

Thatched bungalows on the Pacific coast of Mexico; access to prime surfing spots and acclaimed resort restaurant

$562 $289

Secluded Island Resort in Puerto Rico

Sea Breeze Hotel

Culebra, Puerto Rico

A suite hotel on the beautiful island of Culebra located just off of Puerto Rico, minutes from world-class beaches and snorkeling

$378 $199