Oliveto Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Oliveto Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
$1,620
per person
Oct 27 - Nov 2
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this spa hotel in Florence. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Ponte Vecchio are located nearby.
Stunning hotel and maintained to a spotless standard. Bit of a trek to the centre and parking not cheap but good services just outside (tram, bus) - just takes some working out. We probably didn't need to go for the suite considering the time of year (Sauna and jacuzzi not overly used after stomping streets in near 40deg heat!). Breakfast good and staff super friendly/informative.
Reviewed on Aug 11, 2026
Eden Rock Resort
$1,994
per person
Oct 21 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this business-friendly residence in Florence. Enjoy free WiFi, room service, and parking (surcharge). Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on Jul 18, 2026
The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World
Historic Centre of Florence
$5,178
per person
Oct 21 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and room service. Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.
IQ Hotel Firenze
Historic Centre of Florence
$1,698
per person
Oct 21 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this spa hotel in Florence. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.
Friendly staff and very clean. The pool was refreshing on the hot days and the location was good. Easy to walk everywhere.
Reviewed on Aug 13, 2026
Corte Guelfa
Historic Centre of Florence
$1,621
per person
Oct 27 - Nov 2
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Stay at this residence in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cathedral of Santa Maria del Fiore and Piazza del Duomo are located nearby.
Bernini Palace
Historic Centre of Florence
$2,928
per person
Oct 21 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Piazza della Signoria and Ponte Vecchio are located nearby.
Top Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Borgo Scopeto Wine & Country Relais
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Book a stay at this luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Book a stay at this business-friendly B&B in Castelnuovo Berardenga. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and ...
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
Book a stay at this spa hotel in Gaiole in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gaiole in Chianti Stadium and Castello ...
Borgo San Felice Resort
San Felice Castelnuovo Berardenga SI
Book a stay at this luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Popular attractions San Felice Winery and Castle ...
Castello di Leonina Relais
Strada Di Leonina 5 Asciano SI
Book a stay at this spa hotel in Asciano. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Siena Circuit and Torre dell'Orologio are located ...
Hotel Le Fontanelle
SP 408-km 14.7 Castelnuovo Berardenga SI
Book a stay at this luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Piazza del Campo and Chianti ...
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Museo Diocesano and Santa Maria Nuova are ...
Dievole Wine Resort
Loc. Dievole 6 / Vagliagli Castelnuovo Berardenga SI
Book a stay at this luxury guesthouse in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
B&B Hotel Arezzo
Via Einstein, 4 Arezzo AR
Book a stay at this business-friendly hotel in Arezzo. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions UCI Cinemas Arezzo and Porta ...
Hotel Continentale
Piazza Guido Monaco, 7 Arezzo AR
Book a stay at this business-friendly hotel in Arezzo. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Piazza Grande and Piazza ...
Il Gentiluomo Hotel & SPA
Via Raccordo Autostradale, 1/a Arezzo AR
Book a stay at this spa hotel in Arezzo. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Arezzo Equestrian Centre and Area Naturale ...
Hotel Minerva
Via Fiorentina, 4 Arezzo AR
Book a stay at this business-friendly hotel in Arezzo. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Castello di Tornano Wine Resort
Loc. Tornano Gaiole in Chianti SI
Book a stay at this luxury farm stay in Gaiole in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Meleto Castle and Castello ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Sep 17 - Wed, Sep 23
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$249
Roundtrip
found 2 days ago
Wed, Oct 21 - Wed, Nov 4
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$253
Roundtrip
found 2 days ago
Sun, Oct 18 - Mon, Nov 2
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$299
Roundtrip
found 2 days ago
Thu, Sep 17 - Wed, Sep 23
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$330
Roundtrip
found 2 days ago
Sat, Oct 17 - Mon, Nov 2
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$338
Roundtrip
found 2 days ago
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