Four adults · two rooms · flights separate · home by Sunday, Jan 3

Five grand buys
a very good New Year.

A full week in Puerto Rico—or five nights in a real spa, beach resort or distinctive island hotel. Every priced stay below is for the whole group, and every card opens the exact property and dates.

14verified stays
$1,353lowest lodging total
$3,109average lodging total
7 nightslongest verified stay
01

If seven nights matter most

Puerto Rico

Villa del Sol gives the group a full week for $3,164.

02

If spa + beach matters most

St. Martin

Hommage is $2,727; Oyster Bay is $3,402.

03

If value matters most

Jamaica

Hotel 39 has a spa and rooftop pool for $1,781.

04

If character matters most

St. Croix

The Fred is beachfront, adults-only and $3,386.

The short answer

Five ways to win.

These are ordered by the family tradeoff they solve—not simply by price. The first three are the cleanest decisions; Hotel 39 and The Fred are the two smart wildcards.

Courtyard pool at Hotel Villa del Sol
Expedia gallery
01

Best full week

Hotel Villa del Sol

Isla Verde · San Juan

Seven nights in Isla Verde, an excellent guest score, a pool and a genuinely easy walk to the beach.

Palm-lined garden walkway at Hommage Hotel
Expedia gallery
02

Best spa value

Hommage Hotel & Residences

Nettlé Bay · French side

The cleanest luxury-for-less result: real spa, white-sand beach, two pools and room service for well under budget.

Pool at Oyster Bay Beach Resort
Expedia gallery
03

Best polished resort

Oyster Bay Beach Resort

Oyster Pond · Dutch side

The most complete classic-resort package under the cap: Dawn Beach, infinity pool, spa and a strong review base.

Rooftop pool at Hotel 39 Jamaica
Official property site
04

Best hotel value

Hotel 39 Jamaica

Hip Strip · Montego Bay

A rooftop pool, onsite spa and central location for less than many single rooms cost elsewhere over New Year.

Historic exterior of The Fred in Frederiksted
Official property site
05

Best distinctive boutique

The Fred · Adults Only

Frederiksted · St. Croix

A historic beachfront boutique with spa, pools and real personality—plus direct holiday availability under the cap.

Our recommendation

Choose between Villa del Sol and Hommage first.

Villa del Sol wins on time, simplicity and price. Hommage wins if “this should feel like a resort vacation” is the deciding sentence. Oyster Bay is the polished upgrade; Hotel 39 is the value play.

Date strategy

The tradeoff is simple.

Starting Dec 27 preserves a full week, but the credible sub-$5k results concentrate in Puerto Rico. Starting Dec 29 cuts the stay to five nights and unlocks the real resort/spa set.

The verified board

Compare every stay.

All prices are lodging only for four adults. Hotel results use two rooms; the Anguilla home uses four guests. Taxes and fees are included wherever the booking source displayed them.

14 verified staysPrices checked Aug 27, 2026
Courtyard pool at Hotel Villa del Sol
Expedia gallery
Easy route
Best full week 01

Puerto Rico · Isla Verde · San Juan

Hotel Villa del Sol

$3,164lodging total
Dec 27–Jan 37 nights 9.2/102,148 reviews 2 hotel roomsTwo rooms · seven nights · taxes and fees included
full weekpool1 block to beachrefundableno passport
Why it works

Seven nights in Isla Verde, an excellent guest score, a pool and a genuinely easy walk to the beach.

Know before choosing

A small, friendly hotel—not a full-service resort or spa. Book one dedicated spa day elsewhere.

Getting thereNonstop JFK–SJU; about 5 minutes from the airport.

Expedia · checked Aug 27, 2026 · availability and price can move

Palm-lined garden walkway at Hommage Hotel
Expedia gallery
Easy route
Best spa value 02

St. Martin · Nettlé Bay · French side

Hommage Hotel & Residences

$2,727lodging total
Dec 29–Jan 35 nights 8.4/10731 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
full-service spawhite-sand beach2 poolsrefundable
Why it works

The cleanest luxury-for-less result: real spa, white-sand beach, two pools and room service for well under budget.

Know before choosing

Five nights rather than a full week, and the French-side location is calmer than the Dutch-side nightlife.

Getting thereNonstop JFK–SXM; about 14 minutes from the airport.

Expedia · checked Aug 27, 2026 · availability and price can move

Pool at Oyster Bay Beach Resort
Expedia gallery
Easy route
Best polished resort 03

St. Martin · Oyster Pond · Dutch side

Oyster Bay Beach Resort

$3,402lodging total
Dec 29–Jan 35 nights 8.8/101,003 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
full-service spaDawn Beachinfinity poolrefundable
Why it works

The most complete classic-resort package under the cap: Dawn Beach, infinity pool, spa and a strong review base.

Know before choosing

The east-side location is scenic but not the best base for walking to the island’s main restaurant districts.

Getting thereNonstop JFK–SXM; roughly 35 minutes across the island.

Expedia · checked Aug 27, 2026 · availability and price can move

Rooftop pool at Hotel 39 Jamaica
Official property site
Easy route
Best hotel value 04

Jamaica · Hip Strip · Montego Bay

Hotel 39 Jamaica

$1,781lodging total
Dec 29–Jan 35 nights 8.6/10818 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
sparooftop poolnear beachcentralbest price
Why it works

A rooftop pool, onsite spa and central location for less than many single rooms cost elsewhere over New Year.

Know before choosing

It is a city boutique base, not an enclosed beach resort; Doctor’s Cave Beach is nearby rather than private.

Getting thereNonstop JFK–MBJ; about 8 minutes from the airport.

Expedia · checked Aug 27, 2026 · availability and price can move

Historic exterior of The Fred in Frederiksted
Official property site
Moderate route
Best distinctive boutique 05

U.S. Virgin Islands · Frederiksted · St. Croix

The Fred · Adults Only

$3,386lodging total
Dec 29–Jan 35 nights 8.4/10351 reviews 2 available roomsTwo displayed available room totals summed · five nights
beachfrontspaadults-only2 poolsdirect rate
Why it works

A historic beachfront boutique with spa, pools and real personality—plus direct holiday availability under the cap.

Know before choosing

The quoted pair mixes a queen sea-view room and a king garden-view room; the direct rate requires a 50% deposit.

Getting thereUsually one stop JFK–STX; about 20 minutes from the airport.

Direct hotel booking · checked Aug 27, 2026 · availability and price can move

Caribbean view at SeaGarden Beach Resort
Official property site
Easy route
Best prepaid simplicity 06

Jamaica · Montego Bay

SeaGarden Beach Resort · All Inclusive

$3,760lodging total
Dec 29–Jan 35 nights 7.6/102,217 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
all-inclusiveprivate beach clubpoolspa treatmentsrefundable
Why it works

The easiest resort budget: beach club, pool and all-inclusive rate without taking lodging anywhere near $5,000.

Know before choosing

The 7.6 score is the weakest finalist. This is solid midrange convenience, not quiet five-star luxury.

Getting thereNonstop JFK–MBJ; a short prearranged transfer.

Expedia · checked Aug 27, 2026 · availability and price can move

Beach, pool and ocean at The Palms Hotel and Spa
Hotels.com gallery
Easy route
Best no-island luxury 07

Miami · Mid-Beach · Miami Beach

The Palms Hotel & Spa

$5,000lodging total
Dec 29–Jan 35 nights 9.2/101,916 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
full-service spabeachfrontheated poolluxury
Why it works

A true beachfront spa hotel with an excellent score, warm-weather ease and no international logistics.

Know before choosing

Exactly at the lodging ceiling before any rate movement; the islands should feel warmer and more transporting.

Getting thereMany nonstop JFK/LGA–MIA flights; about 25 minutes from MIA.

Hotels.com · checked Aug 27, 2026 · availability and price can move

Turquoise water and beach near Seaside Splendor
Expedia gallery
Boat transfer
Best family layout 08

Anguilla · Sandy Hill Bay

Seaside Splendor

$2,280lodging total
Dec 29–Jan 35 nights 9.4/1044 reviews Whole home · 3 bedroomsEntire home · five nights · taxes and fees included
3 bedrooms2 bathspool5-minute walk to beachkitchen
Why it works

Everyone gets a real bedroom, with a pool, deck and beach access for less than half the lodging budget.

Know before choosing

No hotel service or spa, only 44 reviews, and Anguilla adds a boat transfer on both ends.

Getting thereNonstop JFK–SXM, then ferry or boat transfer to Anguilla.

Expedia vacation rental · checked Aug 27, 2026 · availability and price can move

Art Deco exterior of Hotel Greystone
Official property site
Easy route
Best polished Miami value 09

Miami · South Beach

Hotel Greystone · Adults Only

$3,686lodging total
Dec 29–Jan 35 nights 9.0/101,000 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
adults-onlyrooftop poolnear beachdesign hotel
Why it works

Adults-only calm, a rooftop pool and strong reviews at more than $1,300 under the ceiling.

Know before choosing

Beach service rather than direct beachfront, and no full spa complex.

Getting thereMany nonstop JFK/LGA–MIA flights; no car needed in South Beach.

Hotels.com · checked Aug 27, 2026 · availability and price can move

Pool at La Vue Boutique Inn
Official property site
Boat transfer
Best Anguilla hotel value 10

Anguilla · South Hill

La Vue Boutique Inn

$3,573lodging total
Dec 29–Jan 35 nights 9.0/10260 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
poolpanoramic viewrestaurantisland base
Why it works

A well-reviewed, personal boutique hotel with sunset views and a pool, leaving plenty of lodging budget for nicer rooms.

Know before choosing

Hillside, not beachfront, and no onsite spa; this works best with a rental car or trusted driver.

Getting thereNonstop JFK–SXM, then ferry or boat transfer to Anguilla.

Expedia · checked Aug 27, 2026 · availability and price can move

Pool and white buildings at Anchors Hotel
Official property site
Moderate route
Best east-coast Puerto Rico base 11

Puerto Rico · Sardinera · Fajardo

Anchors Hotel

$2,843lodging total
Dec 27–Jan 37 nights 9.4/10213 reviews 2 hotel roomsTwo rooms · seven nights · taxes and fees included
full weekpoolrefundableFajardono passport
Why it works

A full week with an exceptional score near Fajardo’s marinas, Seven Seas and the El Yunque side of the island.

Know before choosing

This is not San Juan. A rental car is strongly recommended, and it is a boutique base rather than a spa resort.

Getting thereNonstop JFK–SJU, then roughly an hour by car to Fajardo.

Expedia · checked Aug 27, 2026 · availability and price can move

Outdoor pool at Courtyard San Juan Miramar
Official property site
Easy route
Best familiar-brand full week 12

Puerto Rico · Miramar · San Juan

Courtyard by Marriott San Juan Miramar

$4,203lodging total
Dec 27–Jan 37 nights 8.6/101,000 reviews 2 hotel roomsTwo rooms · seven nights · taxes and fees included
full weekpoolMarriottrefundableno passport
Why it works

Seven nights with predictable Marriott operations, a pool and easy access to Condado and Old San Juan.

Know before choosing

Miramar is urban and not beachfront. Villa del Sol is the better value; this is the safer brand choice.

Getting thereNonstop JFK–SJU; about 15 minutes from the airport.

Expedia · checked Aug 27, 2026 · availability and price can move

Art Deco exterior of The Tony Hotel South Beach
Official property site
Easy route
Best Miami price 13

Miami · South Beach

The Tony Hotel South Beach

$2,364lodging total
Dec 29–Jan 35 nights 9.0/101,365 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
rooftop poolnear beachArt Decobest price
Why it works

A 9.0-rated South Beach hotel with a rooftop pool at less than half the lodging ceiling.

Know before choosing

No spa and a livelier neighborhood; request quieter rooms away from the street.

Getting thereMany nonstop JFK/LGA–MIA flights; no car needed in South Beach.

Hotels.com · checked Aug 27, 2026 · availability and price can move

Pool at Toby’s Resort
Official property site
Easy route
Lowest hotel total 14

Jamaica · Hip Strip · Montego Bay

Toby’s Resort

$1,353lodging total
Dec 29–Jan 35 nights 8.6/101,413 reviews 2 hotel roomsTwo rooms · five nights · taxes and fees included
poolwalk to beachfamily-ownedlowest price
Why it works

The cheapest credible two-room hotel on the board, with a real pool and a large review base.

Know before choosing

Simple and cheerful rather than luxurious; choose Hotel 39 if Pascale wants a spa onsite.

Getting thereNonstop JFK–MBJ; only a few minutes from the airport.

Expedia · checked Aug 27, 2026 · availability and price can move

The geography

See the actual places.

Green markers are priced finalists; coral markers are strong properties still awaiting a reliable holiday total. The map uses OpenStreetMap geography.

Map data © OpenStreetMap contributors. Pins represent property locations, not a decorative approximation.

Worth keeping open

Two unpriced contenders.

They fit the property brief, but not yet the evidence bar. Neither is counted as under $5,000 until a live checkout page returns a two-room total.

Tropical grounds at Hôtel Bambou and Spa
Official property site

Martinique · price pending

Hôtel Bambou & Spa

Beachfront, two pools, a full spa and an 8.6 score—the best unpriced match to the brief.

Route

Usually one stop from JFK to FDF; about 40 minutes to Trois-Îlets.

Status

Exact holiday availability loaded, but the booking source did not return a two-room price. Recheck before promoting it into the shortlist.

Wyndham Tortola Lambert Beach Resort from above
Official property site

British Virgin Islands · price pending

Wyndham Tortola BVI Lambert Beach Resort

A real beach resort with one of Tortola’s largest pools and an onsite spa.

Route

One stop to EIS or fly to STT and continue by ferry; this is a higher-friction route.

Status

The property is compelling, but no reliable two-room holiday total surfaced. It stays off the under-$5k board until repriced.

Flights are a separate decision

Use points where they save real cash.

The lodging board does not include flights, food, transfers or activities. That keeps the decision honest and lets Chase, Bilt and JetBlue points compete against cash fares independently.

01

Hold the refundable stay

Where the exact listing is refundable, lock the room before the holiday inventory tightens. Recheck the cancellation deadline at checkout.

02

Price four cash tickets

Start with the best practical itinerary—not the absolute cheapest fare if it introduces an overnight or exhausting layover.

03

Compare points one traveler at a time

Check JetBlue TrueBlue, Chase Travel and Bilt. Mix points and cash only when the cents-per-point value is respectable and the itinerary stays together.

04

Then test the Expedia package

Compare the exact same rooms and flights as a package. A package only wins if its final total and cancellation terms beat the separated booking.

Fastest decision

Villa del Sol

Seven nights, easy route, $3,164 lodging.

Best vacation feeling

Hommage

Spa, beach, two pools, $2,727 lodging.

Best clever value

Hotel 39

Spa + rooftop pool, $1,781 lodging.

Read this before booking

What the numbers mean.

Scope

Four adults. Hotel quotes use two rooms with two adults in each. The Anguilla home uses four adults. No meals, flights, transfers, activities or local transport are included in the lodging ceiling.

Prices

Totals were read from dated property pages on Aug 27, 2026. Most explicitly included taxes and fees. The Fred total is the sum of the two lowest available room totals shown by its direct booking engine.

Ratings

Scores and review counts are the booking source’s displayed figures, not a private quality score. SeaGarden’s lower 7.6 rating is why it ranks below cheaper and better-reviewed alternatives.

Links

Every “exact listing” button points to the property—not a generic Expedia or Hotels.com homepage—and includes the researched dates and room configuration.

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